The three pastoral letters or epistles are books of the canonical New Testament: the First Epistle to Timothy (1 Timothy) the Second Epistle to Timothy (2 Timothy) and the Epistle to Titus. They are letters from Paul the Apostle to Timothy and to Titus. They are generally discussed as a group (sometimes with the addition of the Epistle to Philemon) and are given the title pastoral because they are addressed to individuals with pastoral oversight of churches and discuss issues of Christian living, doctrine and leadership. While the title is not technically quite correct in that the Epistles do not deal with pastoral duties in the sense of the cure of souls, yet it is popularly appropriate as denoting the essentially practical nature of the subject matter as distinguished from the other Epistles attributed to Paul. The term "pastorals" was popularised in 1703 by D. N. Berdot and in 1726 by Paul Anton.

Titus 3:3 We were

Titus 3:3 At one time we too were foolish, disobedient, deceived and enslaved by all kinds of passions and pleasures. We lived in malice and envy, being hated and hating one another.
In more than one place the New Testament describes life before Christ, the life all believers lived before coming to know him, especially those outside Judaism. Paul uses a number of words or phrases to describe how it was in the past here in Titus 3:3. By nature we were foolish - morally corrupt; we were disobedient - unwilling and unable to obey God; deceived - how little did we understand of our plight and how to be delivered from it; enslaved by all kinds of passions and pleasures - we thought we were free but far from it, we had no choice but to follow our desires; there was also those twin evils of malice and envy. On the one hand we were hated by others and on the other we were those who were hating others. What a hopeless mess it was. This is how it continues to be for the unbeliever. What misery they know, misery that can only be removed in Christ.

Titus 2:11 All People

Titus 2:11 For the grace of God has appeared that offers salvation to all people.
The word For alerts us to the fact that there is a connection between Titus 2:9 and what has gone before. What has gone before is instruction for Titus on the need to teach different groups in the church (older and younger men, older and younger women and slaves). This would suggest that the all people in the verse is not absolute but refers to different types of people (older and younger men, older and younger women and slaves). Paul's point then is that all sorts of people need to be taught how to live the Christian life because the grace of God has appeared that offers salvation to all people. The first part of the verse is a little like the phrase that appears in Titus 3:4 the kindness and love of God our Saviour appeared. In both cases Paul is thinking of the incarnation that being the quintessential appearing of the grace or free and loving favour of God. This grace "brings" or  offers salvation to all people. There is no verb so that has to be supplied and one could argue over that. That point, however, is that salvation has begun to be offered and indeed comes to all sorts of people now that the grace of God has appeared. Ministers and their churches, therefore, must never be narrow in who they offer the gospel to or who they encourage to live the Christian life.

Titus 2:3-5 Women's Lessons

Titus 2:3-5 Likewise, teach the older women to be reverent in the way they live, not to be slanderers or addicted to much wine, but to teach what is good. Then they can urge the younger women to love their husbands and children, to be self-controlled and pure, to be busy at home, to be kind, and to be subject to their husbands, so that no one will malign the word of God.
In Titus 2 Titus is taught that he must teach what is appropriate to sound doctrine and do this bearing in mind the sort of people in the churches - older men, younger men, older women and younger women. In verses 3-5 he cleverly rolls the instructions to the younger women into what the older women are to be told. Older women are told positively to be reverent in the way they live and to teach what is good and negatively not to be slanderers or addicted to much wine something that could easily happen with time on their hands. By this means they will be a good influence on the rising generation of women who they can urge in at least five things - loving their husbands and children, being self-controlled and pure, being busy at home, being kind, and being subject to their husbands. The pastors role is clearly not to teach young women but to he is to teach the older women - encouraging reverence and warning against gossip and drink and helping them to teach the younger women to love their families, subject to their husbands, be self-controlled and pure, work hard at home and be kind in general. Paul sees this is vital because the last thing they needed in Crete was to give people an excuse to malign the word of God. No churches want that.

Titus 1:10 Vain-talkers, Mind-deceivers

Titus 1:10 For there are many rebellious people, full of meaningless talk and deception, especially those of the circumcision group.
What Paul says to Titus in his own day is probably true to some extent of every period. There are many with a rebellious spirit. Such people are full of meaningless talk and deception. These vain-talkers and mind-deceivers have a great deal to say but it is both empty and deceptive. Paul singles out the circumcision group but such rebels can be found in other forms. Like the circumcision group they have a veneer of religion but in truth they are rebels who are empty and insincere hypocrites who oppose the truth and must be resisted. 1 Timothy 1:6 also refers to meaningless talkers and this strand of thought is found throughout the pastoral letters. See 1 Timothy 1:4-6, 6:3-5, 2 Timothy 3:13, 4:4. The faithful minister will expect such rebellion and warn his people against it while avoiding rebellion, empty talk, deceit and all forms of hypocrisy and false religion himself.

Titus 1:5 Left Unfinished

Titus 1:5 The reason I left you in Crete was that you might put in order what was left unfinished and appoint elders in every town, as I directed you.
In this verse Paul summarises why he left Titus on the island of Crete and what he wanted him to do. The reason Titus was there, in general terms, was that he might put in order what was left unfinished or lacking - the things that remain to be done. The work of planting churches had now been completed but there was still work to be done and it was to be Titus's task to see that it was done. A top priority for him was to be the appointing of elders in every town. Paul had previously spoken to Titus about this but here he reminds him of his task. Once churches have been planted there is still work to be done, if they are to be truly for the glory of God. The appointing of elders is an essential part of the work and one that should be given some priority. It is in the light of this need that Paul later reminds Titus of the sort of men they are looking for to carry out this task. The mechanics of appointing these elders is not spelled out but the more important matter of the sort of men to be sought is.

2 Timothy 4:16, 17 God's Deliverance

2 Timothy 4:16, 17 At my first defence, no one came to my support, but everyone deserted me. May it not be held against them.  But the Lord stood at my side and gave me strength, so that through me the message might be fully proclaimed and all the Gentiles might hear it. And I was delivered from the lion’s mouth.
Here Paul explains how defending himself against the opposition of the Roman authorities (probably at the beginning of his last trial) no one came to his support, but everyone deserted him. Immediately, he adds May it not be held against them. Paul knew better than to seek personal vengeance. He was not dismayed either, even though he was left alone, because, as had happened at other times, the Lord stood at his side and gave him strength (poured power into him). This meant that through Paul the message was fully proclaimed so that all the Gentiles might hear it. Further, he was, he says, delivered from the lion’s mouth which may be a reference to Caesar (Nero) or possibly to Satan or is perhaps even a literal reference. These verses are every specific to Paul but the lessons are more general - sometimes believers do let us down but we must not hold it against them. We can always expect God's help even though men fail us, especially if the gospel is advanced.

2 Timothy 4:11, 12 Fellow Workers

2 Timothy 4:12 Only Luke is with me. Get Mark and bring him with you, because he is helpful to me in my ministry.  I sent Tychicus to Ephesus.
These verse mention three of Paul's fellow workers, two of them famous as Gospel writers and the third much less well known. Luke is the author of the third Gospel and also of Acts. He was a companion of Paul and evidently a medical doctor. There are various ideas about Luke's background but it seems he was a Gentile, perhaps from Antioch and converted under Paul's early ministry there with Barnabas. Clearly he travelled with Paul on his missionary journeys and there is evidence to connect him closely with the church at Philippi in the early days. Here it is Luke's loyalty that is emphasised. Paul is greatly encouraged by Luke's presence at this difficult time. Mark, of course, is another Gospel writer and another missionary companion to Paul, although we know that initial experience turned out rather badly at the end. Here that early disappointment is forgotten and although Mark is not with Paul at the moment Paul desires it because he feels Mark is helpful to me in my ministry. Paul feels in contrast that he can spare Tychicus, who he has sent to Timothy in Ephesus. Tychicus is another companion of Paul mentioned five times altogether in the New Testament. He went from his native Asia (probably Ephesus) to Macedonia with Paul (Acts 20:4) and is mentioned in the Ephesian and Colossian letters as a dear brother ... a faithful minister and ... a faithful servant in the Lord (Ephesians 6:21; Colossians 4:7). He is also mentioned in Titus 3:12 and may have travelled to Crete on Paul's behalf. He is another of the unsung heroes of the New Testament, faithfully serving wherever needed. Loyalty, helpfulness and service are such needed virtues in churches to this day.

2 Timothy 4:7 Task Complete

2 Timothy 4:7 I have fought the good fight, I have finished the race, I have kept the faith.
2 Timothy 4:7 glances back to Chapter 2 and the references in verses 4-6 to serving as a soldier competing as an athlete though probably not The hardworking farmer but the humble servant of verse 24. Paul can say in all humility that as death approaches, as for soldiering, he has fought the good fight, (the one he urged Timothy to fight well in, in 1 Timothy 1:18) he has finished the race and he has kept the faith as a humble servant. He has kept it well guarded. It must be wonderful thing to say such things as one draws near to the end of one's ministry. The only way it can happen, of course, is if today we fight and run and serve as we ought to. What an example Paul was to Timothy and to us too. The fight is against the flesh, the world and the devil, the race is to heaven along the track marked out by the Lord and the service required is to faithfully keep the true doctrines in our hearts without letting them fall to the ground and defending them from attack. All this is done only through the grace of the God Paul served and Timothy too.

2 Timothy 3:2-4 Last Days

2 Timothy 3:2-4 People will be lovers of themselves, lovers of money, boastful, proud, abusive, disobedient to their parents, ungrateful, unholy, without love, unforgiving, slanderous, without self-control, brutal, not lovers of the good, treacherous, rash, conceited, lovers of pleasure rather than lovers of God –
These verses list 18 characteristics of those who will be found in the world in these last days. In each case Paul uses mostly single words to describe these people. They are self-lovers, money-lovers, boasters, proud, blasphemers, disobedient to parents, unthankful, unholy, truce-breakers, hard-hearted, slanderers (or devils), unself-controlled, untamed, not loving the good (only here), traitors, headstrong, puffed up, pleasure lovers rather than God lovers. Such verses warn us both what to expect even from people who profess to be Christians and the sorts of things that we who are true believers must also be aware of and seek to run from so that we love others, avoid the love of money, remain humble, speak purely, obey those in authority, give thanks, be holy, be honest, be loving, speak kindly, be self-controlled, be quiet, love the good, be loyal, keep your head, and love God rather than pleasure.

2 Timothy 2:25, 26 Gentle Instruction

2 Timothy 2:25, 26 Opponents must be gently instructed, in the hope that God will grant them repentance leading them to a knowledge of the truth, and that they will come to their senses and escape from the trap of the devil, who has taken them captive to do his will.
These verses describe how Timothy or others like him should deal with opposition or with opponents. The basic idea is that they should be gently instructed that is taught or trained with meekness. This is in contrast to the arrogant and argumentative approach that he might be tempted to fall into. The hope is that by this means God will grant them repentance or change their minds, which will lead them to a knowledge of the truth. Once they come to their senses in this way they will escape from the trap of the devil, who has taken them captive to do his will. This is a very optimistic approach when we consider that Paul clearly has in mind people who are stubborn and lack repentance, who are ignorant of the truth, senseless and trapped by the Devil, who is currently getting them to do his will. However, we cannot simply give up on people straight away. We must do all we can to win them back.

2 Timothy 2:18 Truth Denied

2 Timothy 2:18 who have departed from the truth. They say that the resurrection has already taken place, and they destroy the faith of some.
2 Timothy 2:18 refers to Hymenaeus and Philetus, referred to in the previous verses and who are examples of the godless chatter, which if indulged in leads to greater and greater ungodliness. It spreads like gangrene. These men Paul is in no doubt have departed from the truth. One of the false things they were saying was that the resurrection has already taken place. This was believed by some and was destroying their faith, as such a notion must obviously do. On what basis such people claimed the resurrection had already passed we do not know. It is unlikely that they thought the resurrection in connection with Christ's own resurrection was the resurrection. it is more likely that they were saying that new birth is the only resurrection or that when a Christian dies he rises to a form of life and there is no more. Heresies come in all shapes and sizes. The important thing is that we take care not to deviate from the truth and that we do all we can to help those whose faith is in danger of being overthrown by such nonsense.

2 Timothy 2:2 Timothy Principle

2 Timothy 2:2 And the things you have heard me say in the presence of many witnesses entrust to reliable people who will also be qualified to teach others.
This verse has become something of a mantra to some in recent years and people even speak of the Timothy principle, usually in reference to one to one discipleship programmes. It would be wrong to narrow down the verse as though it was teaching some particular way of discipling others. Paul simply urges Timothy to teach others just as he himself has taught Timothy. First, then there is Paul, representative of the apostles. Then there is Timothy, representative of the next generation - people who knew the apostles but not Christ on earth. Thirdly, there are those reliable people who knew neither Christ or his apostles but to whom Timothy is to entrust the truth. Fourthly and finally, there are others who learn from them. So what Timothy heard Paul say in the presence of many witnesses he is to entrust to reliable people who will also be qualified to teach others. In other words Timothy is to have in mind passing on the gospel to later generations. All pastors should share this same concern. What they have from the Word of God they must entrust to reliable people who they preach to with the hope that these people will also be qualified to teach others. This means the message must be clear and faithful but in a form that will connect with succeeding generations.

2 Timothy 1:16-18 Helpful Onesiphorus

2 Timothy 1:16-18 May the Lord show mercy to the household of Onesiphorus, because he often refreshed me and was not ashamed of my chains.  On the contrary, when he was in Rome, he searched hard for me until he found me.  May the Lord grant that he will find mercy from the Lord on that day! You know very well in how many ways he helped me in Ephesus.
Verses 16-18 are about a man called Onesiphorus. We know nothing about this man except what is here (and in the passing reference in 4:19). We are told four things about him. First, that he was eager to do good. Paul says that when he was in Rome, he searched hard for me until he found me no doubt to help the apostle in his need. Second, helping was his default position. Timothy would have been well aware as Paul says of how many ways he helped me in Ephesus. Thirdly, he refreshed or revived Paul in Rome, either by providing physical help or though his very words, perhaps. Fourth, he was not ashamed of my chains. He sounds like a wonderful Christian man. The way Paul writes here suggests he is dead by this point, hence the wish for his household to know mercy and for him to be granted mercy on that day. Onesiphorus is one of the many unsung heroes of the New Testament that we catch only a glimpse of. Their counterparts are alive today and a church that has an Onesiphorus is a church that is blessed indeed. A lot depends on ministers but not everything. Without men who will be eager to do good, who help in different ways, who are able to refresh God's servants and who are not ashamed of Christ and his servants are a real asset. Appropriately, the name means "bringing profit".

2 Timothy 1:12 I know

2 Timothy 1:12 That is why I am suffering as I am. Yet this is no cause for shame, because I know whom I have believed, and am convinced that he is able to guard what I have entrusted to him until that day.
It is because Paul is a herald and an apostle and a teacher of the gospel that he suffers as he does. Most of his troubles came from persecution and the rest was due chiefly to his efforts to take the gospel far and wide and to care for the churches. He is not ashamed of his sufferings in any way because, as he says here, I know whom I have believed, and am convinced that he is able to guard what I have entrusted to him until that day. Paul has not discovered a system or a way of life but has come to know and believe in a person and to him, the Lord Jesus Christ, he has committed himself, his person and all he has and is. He has done this, confident that Christ is able to guard what he has entrusted to him until that day that is the day of judgement. All Christians, and ministers especially, should have the same attitude. Yes we may suffer but we've committed ourselves to the Lord and there is no way that he will ever let us down. We can face the coming day of judgement with great confidence.

2 Timothy 1:3 Constantly Remembering

2 Timothy 1:3 I thank God, whom I serve, as my ancestors did, with a clear conscience, as night and day I constantly remember you in my prayers.
Early in this second letter to Timothy, as in other letters, Paul gives thanks to God, although with a different word to the usual one. "I have gratitude" he says. He refers to God as the God he serves, as my ancestors did, with a clear conscience. This backward glance is probably in preparation for his reference to the sincere faith in your grandmother Lois and in your mother Eunice. Indeed, it is the reminder of this that prompts his thankfulness. We do not know how far Paul had to go back to find godly ancestors but he was descended from Abraham and Jacob and Benjamin. How far back his clear conscience goes is debatable too. Paul is conscious, however, of God's grace down the ages to him, as well as to Timothy. He is thankful to God for this as night and day he constantly remembers Timothy in his prayers. The prayer life of the apostle must have been something to behold. It included not only whole churches but many individuals too. He always remembered those he wanted to pray for. What an example he is to busy pastors to find time to pray and not to forget others.

1 Timothy 6:19, 20 Guard, Reject

1 Timothy 6:19, 20 Timothy, guard what has been entrusted to your care. Turn away from godless chatter and the opposing ideas of what is falsely called knowledge, which some have professed and in so doing have departed from the faith. Grace be with you all.
The very last words of the first letter to Timothy are final words of exhortation to the young pastor followed by a general final blessing. Timothy is told to guard what has been entrusted to his care. He is like a person who has been entrusted with a very valuable gift that he must pass on to the next generation. In particular, Paul wants him to Turn away from godless chatter and the opposing ideas of what is falsely called knowledge. He must reject babbling and opposition of people with their pseudo knowledge. This is what some have professed and in so doing have departed from the faith. The problem of false teachers is every bit as much of a problem today as then and the guarding of the gospel by faithful pastors is so very important. The need of all of us to know the grace of God is a constant one.

1 Timothy 6:7, 8 Be Content

1 Timothy 6:7, 8 For we brought nothing into the world, and we can take nothing out of it. But if we have food and clothing, we will be content with that.
People talk about a simple lifestyle but here is Paul advocating it back in the first century. He observes first that we brought nothing into the world a baby is born naked and with nothing. It will die if it is not provided for pretty quickly. Something similar pertains at the end of life - we can take nothing out of the world. When you die you leave everything behind. In between all that really matters then is that we have food and clothing. As Christians we ought to be content with that as enough, especially when we remember that to desire to be rich is to fall into temptation and a trap and into many foolish and harmful desires that plunge people into ruin and destruction ( 9) For the love of money is a root of all kinds of evil that has often led to people wandering from the faith and piercing themselves with many griefs (10). Godliness with contentment is clearly the thing to aim for. This is probably not so much a matter of lifestyle choices as reminding ourselves of the realities of birth, death and life here on earth. Ministers should set an example in this respect and their teaching should re-enforce these ideas.

1 Timothy 5:23 Drink Wine

1 Timothy 5:23 Stop drinking only water, and use a little wine because of your stomach and your frequent illnesses.
We get the impression that Timothy was a rather timid and, it seems, a fastidious man. This verse suggests that he was in the habit of drinking only water rather than wine, no doubt for reasons of sobriety. The problem was that it was not doing his stomach any good and he was frequently ill. Given the unreliable nature of the water supply in those days he was pursuing a risky strategy and Paul very practically advises that he should abandon this practice and start drinking wine, which being alcoholic was, of course, much safer. This raises a number of issues including the need to look after our health, especially if we are preachers, and the danger of over-conscientiousness being detrimental to a person's overall usefulness. It is Paul's ability to cut through issues and see what really matters that is part of his genius. He sees that fastidiousness about drinking wine is ruining Timothy's health and so must not be allowed to continue. Better to drink wine and be well. The applications of such an understanding are many.

Commentaries - Carson's take

Like others, Don Carson (in his Survey of NT commentaries) chiefly recommends Knight, Marshall and Mounce on the pastorals.
He also mentions J D Quinn on Titus as well as Luke Timothy Johnson and Quinn and Wacker on 1 and 2 Timothy (ECC)
Others he mentions include Conzelmann and Dibelius, D Arichea, Margaret Davies, Houlden, C K Barrett, Reginald Fuller, Guthrie, A T Hanson, Hultgren and Aus, Raymond F Collins, Walter Liefeld, J N D Kelly, Gordon D Fee, Thomas D Lea, Philip Towner, Moule, Stott, Reese, Douglas Milne, Michael Bentley, Bruce Barton, Michael Griffiths, C Michael Moss.
Classics in print he says include Fairbairn, Erdman, Liddon and Calvin.

1 Timothy 5:17 Double Honour

1 Timothy 5:17 The elders who direct the affairs of the church well are worthy of double honour, especially those whose work is preaching and teaching.
At the end of Chapter 5 there is a brief section on elders. In verse 17 Paul mentions elders and he makes two distinctions. First, he speaks of those who direct the affairs of the church well which must refer to outstanding men in the eldership. He then qualifies that with especially those whose work is preaching and teaching. All elders direct the affairs of the church but not in the same way. The latter qualification suggests that not all elders are preaching and teaching elders and the former that not all direct the affairs of the church as well as others. When he says these people are worthy of double honour he probably means not just respect (as in 1 Thessalonians 5:12, 13) but pay, as the context of verse 18 which supports Paul's idea would suggest. There are examples of Roman soldiers being given double pay for outstanding acts. Double what? Perhaps double what the widows were given or double the average or simply a way of saying pay them well. Most elders it seems then are not paid but some are. Those who are paid will most likely be those involved in the preaching and teaching. Most churches that have elders seem aware of these distinctions - not all elders preach, not all elders are paid, those who are paid tend to be the preachers. The idea of paying such people well is still not accepted by some though many do see it.

1 Timothy 5:3, 4 Proper Recognition

1 Timothy 5:3, 4 Give proper recognition to those widows who are really in need.  But if a widow has children or grandchildren, these should learn first of all to put their religion into practice by caring for their own family and so repaying their parents and grandparents, for this is pleasing to God.
It is probably the mention of how Timothy should relate to older women that leads Paul on to speak about widows. Timothy has a responsibility to Give proper recognition to ... widows but only those who are really in need. There seems to have been a list in those days of people who were helped by the church and who helped the church. Today things are different but the need to give proper recognition to those who work in the church continues. Some will be paid staff (ministers, assistant ministers, caretakers, secretaries, musicians) others will act voluntarily (deacons, cleaners, caterers, musicians, etc) but ought to be thanked. What Paul is guarding against here is putting people on the list who should not be on it. If a widow has children or grandchildren, he says these should learn first of all to put their religion into practice by caring for their own family and so repaying their parents and grandparents, for this is pleasing to God. The danger of simply relying on the church to provide money and other physical benefits is a real one and must be avoided. If a church employs staff, it needs to consider whether things can be trimmed down. People must recognise the voluntary principle, especially where their own families are concerned. This is an outworking of the doves and serpents principle that Jesus iterates in the context of mission in Matthew 10.

Commentaries - Yet more recommendations

Michael de Walt mentions

#1 1 & 2 Timothy and Titus, by Patrick Fairbairn
From the preface by the author. This expository volume on the Pastoral Epistles had its origin in a department of labour connected with my official duties. Till lately, it was for many years my lot to conduct a class of Pastoral Theology for advanced students preparing for the work of the Christian ministry; and a portion of the time during each session was usually devoted to the exposition and illustration of more or less of those Epistles. Practically, it was found impossible to overtake more, in any particular session that a comparatively limited portion of them. But as comments on the whole had been prepared, I have thought that the publication of them might be of some advantage to students of Sacred Scripture, especially those who are either in the position of candidates for the ministry, or without lengthened experiences in the discharge of its duties.

#2 Sermons on 1 & 2 Timothy and Titus, by John Calvin
John Calvin still speaks through timeless works such as this one, where he explores the aging Paul’s pastoral counsel to two younger apostles on church and doctrinal issues. Abridged and adapted for today’s reader.

#3 The Message of 1 Timothy & Titus: The Bible Speaks Today Series, by John Stott
For the postmodern world the very notion of objective truth is open to question if not ridicule. In a cultural climate of soft footings and cracking walls, Paul’s unambiguous commitment to the church as "the pillar and foundation of the truth" is a timely metaphor. It calls us to reconsider the architecture of a truly Christian worldview and to re-examine the gospel and tradition we have inherited. Paul’s burden in these letters to Timothy and Titus is inheritance, the faithful guarding and delivering of the inheritance of gospel truth. Nearing the end of his life, Paul is intent on securing the heritage of gospel truth for the next generation.

#4 2 Timothy: MacArthur New Testament Commentary, by John MacArthur
In the face of spiritual warfare and the daily bombardment of worldly evils, you need a message of encouragement to "fight the good fight." The ammunition? MacArthur’s motivating commentary on doctrinal truths and church life armed with a bibliography and subject, Scripture, and Greek word indexes. About 224 pages, hardcover from Moody.

#5 A commentary upon the Epistle of St. Paul written to Titus, by Thomas Taylor
C. H. Spurgeon said, "The title-page calls Thomas Taylor ‘a famous and mast elaborate divine.’ He was a preacher at Paul’s Cross during the reigns of Elizabeth and James I, and a voluminous writer. This Commentary will well repay the reader."
*
Andreas Kostenberger goes for

Johnson, Luke Timothy. Letters to Paul’s Delegates: 1 Timothy, 2 Timothy, Titus. New Testament in Context. Valley Forge, PA: Trinity Press International, 1996.
Knight, George W. III. The Pastoral Epistles. NIGTC. Grand Rapids: Eerdmans, 1992.
Köstenberger, Andreas J. “1 and 2 Timothy, Titus.” EBC. Rev. ed. Grand Rapids: Zondervan, 2006, 487–625.
Marshall, I. Howard. The Pastoral Epistles. ICC. Edinburgh: T. & T. Clark, 1999.
Mounce, William D. Pastoral Epistles. WBC. Nashville: Thomas Nelson, 2000.
Quinn, Jerome D. and William C. Wacker. The First and Second Letters to Timothy. ECC. Grand Rapids: Eerdmans, 2000.
Towner, Philip H. The Letters to Timothy and Titus. NICNT. Grand Rapids: Eerdmans, 2006.
 
Tom Schreiner also recommends Knight, Marshall and Mounce.

Commentaries - Grace Online Recommendations

 Pastoral Epistles (WBC) by William D. Mounce

Commentaries - More recommendations

One non-commentary I ought to mention is the collection of essays edited by Andreas J. Köstenberger and Terry Wilder, Entrusted with the Gospel: Paul’s Theology in the Pastoral Epistles (Nashville: Broadman & Holman, 2010). Wilder deals with the problem of authorship in one of the first essays, and I. Howard Marshall contributes an essay on the Pastorals in Recent Study. On the issue of Paul’s statement on women see the essays collected in by Andreas J. Köstenberger, Thomas R. Schreiner, and H. Scott Baldwin, Women in the Church: A Fresh Analysis of 1 Timothy 2:9-15 (Grand Rapids, Mich.: Baker, 1995).
 
I. Howard Marshall, The Pastoral Letters (ICC; Edinburgh: T&T Clark, 2004). Marshall’s contribution is perhaps the most detailed exegetical commentary on the list, as is to be expected from an ICC volume. Marshall replaced Walter Lock’s 1924 commentary in the series. The book caused a stir when it was released since Marshall (beloved by many evangelicals) rejected Pauline authorship of these letters. The introduction to the commentary develops Marshall’s view of authorship. The body of the commentary contains detailed bibliographies for each section followed by an overview of the text. The format of the commentary is a phrase-by-phrase unpacking of the Greek text, including textual, lexical and syntactical issues. He interacts with a broad range of scholarship, with Marshall includes a number of excellent excursuses (on Household Codes, in Titus, for example).
 
Philip H. Towner, The Letters to Timothy and Titus (NICNT; Grand Rapids, Mich.: Eerdmans, 2006); 1-2 Timothy & Titus (IVPNTC; Downers Grove, Ill: InterVarsity, 1994). Towner’s recent commentary in the New International Commentary series is an excellent exegetical commentary. The body of the commentary proceeds through the text phrase-by-phrase, with Greek treated in the footnotes in detail.  Towner has excellent exegetical notes and also demonstrates a expertise in Greco-Roman literature as well, especially in the virtue/vice lists.  I also mention here his IVP volume, written more than ten years before the larger commentary. This series is designed for busy pastors who need a basic commentary, although an interested layman would find this a very readable commentary. His comments are on the English Bible and all references to Greek are in footnotes.
 
Luke Timothy Johnson, The First and Second Letters to Timothy (AB; New Haven: Yale University, 2001). Johnson is one of the more prolific New Testament scholars, and his Anchor Bible volume on the letters to Timothy is one of the best of the series. He spends about fifty pages on the authorship of the Pastorals, fairly describing and assessing the “conventional approach.” He offers five problems which this consensus view rarely discusses, and finally settles on the view that these letters are genuinely Pauline. He knows that authenticity cannot be demonstrated, but he sees these letters are representing Paul’s own thinking even if they are written through a delegate of some kind. As with all the Anchor commentaries, the body of the commentary includes a fresh translation followed by phrase-by-phrase notes, all Greek is transliterated. After the notes, Johnson provides a comment section which deals with the overall themes of the section, usually including the special contribution of the section to a kind of “pastoral epistles theology.” Johnson does not include Titus in this volume. The Anchor Bible series has a separate volume for Titus, Jerome D. Quinn, The Letter to Titus (AB; New Your: Doubleday, 1990). Quinn, who died before finishing this commentary, includes an introduction on all three pastoral letters. (Ben Witherington calls Quinn’s commentary the “only real standout” commentary on Titus.  He may be right, since there are precious few commentaries on Titus alone!)
 
William D. Mounce, Pastoral Epistles (WBC; Nashville: Thomas Nelson, 2000). While he is better known for his ubiquitous Greek Grammar, Mounce has produced a fine commentary on the Pastoral Epistles. His introduction is very well written and is a good overview of the methodological issues which stand behind the problem of authorship. Mounce settles on a form of amanuensis theory to explain the differences between the Pastorals and the other letters of Paul. He includes an excursus on Pseudepigraphy and Canon which is one of the better overviews of the problem I have read. (The introduction is 136 pages; I wish that the Word series would dispense with Roman numerals for introductions when they run this long!) The body of the commentary follows the pattern of the Word series: Bibliography, followed by a fresh translation with textual notes, form/structure, formal commentary and explanation. The Formal commentary is on the Greek text without transliteration, and like the rest of the series, there are no footnotes, all sources are cited in-text. As might be expected, Mounce’s comments on the syntax of the Greek are detailed, but he does not merely identify forms, he consistently draws out theological conclusions based on his exegesis.
 
Ben Witherington III, Letters and Homilies to Hellenized Christians. Volume 1 (Downers Grove, Ill.: InterVarsity, 2006). Witherington’s socio-rhetorical commentary for the Pastoral Epistles was published by IVP rather than Eerdmans, and under the title this more verbose title. If you do not read the subtitles, you might miss the fact that the three volumes are commentaries. They are roughly the same style as the other socio-rhetorical commentaries, providing notes on the English text with Greek transliterated. As with his other similar commentaries, Witherington attempts to read these letters as examples of Greco-Roman rhetoric categories. An interesting wrinkle in this series is that he starts with Titus, rather than 1 Timothy. Usually commentaries start with Timothy and give Titus too little attention. I do find it odd that he includes the letters of John in this volume, making it impossible for me to put the book in a proper place on my OCD shelf.
 
Conclusion. There are a few books I left off this list to keep it to five.  Even though I slipped a few extras into the mix, there are a number of good commentaries I know I have omitted.
 

Commentaries - Tim Challies Recommends

George W. Knight, III - The Pastoral Epistles (New International Greek Testament Commentary). D.A. Carson lists more “best buys” for the pastoral epistles than for any other book or books and at the very top of his list is Knight’s volume in the NIGTC which he commends as “cautious, conservative and thoughtful.” As you may know, this series is quite technical and requires at least some knowledge of Greek. If you know Greek and are teaching or preaching one of the pastoral epistles, you will want to add this volume to your collection post haste.

I. Howard Marshall - The Pastoral Epistles (International Critical Commentary). After commending Knight, Carson also commends Marshall and says his work is “packed with thoughtful, well-written reflection on every issue of importance.” Yet, oddly, Marshall does not believe that the epistles were written by Paul and this, not surprisingly, influences some of his interpretations. Still, it receives high recommendations and will prove valuable, especially for the teacher or preacher.

William D. Mounce - Pastoral Epistles (Word Biblical Commentary). The experts all recommend this one. Keith Mathison writes, “Many will recognize William D. Mounce as the author of the widely used Basics of Biblical Greek Grammar. His commentary on the Pastoral Epistles in the Word series is very helpful. Mounce thoroughly discusses all of the important issues raised by Paul (whom he believes wrote these epistles), and when dealing with controversial parts of the letters, he fairly represents those with whom he disagrees. All in all, a very good commentary.”

Philip H. Towner - The Letters to Timothy And Titus (New International Commentary on the New Testament). While not as technical as George Knight’s volume, this one still weighs in at a hefty 900 pages and should probably be the first choice for teacher or preachers who do not have knowledge of Greek and, therefore, cannot get a lot out of the NIGTC. Towner provides a conservative interpretation that assumes Pauline authorship.

Donald Guthrie - The Pastoral Epistles (Tyndale New Testament Commentaries). I always try to include at least one volume that is reader-friendly and suitable for someone who wants to do a relatively light study. Guthrie’s fits the bill. He writes from a conservative position, addresses those who take an opposing view, and then helpfully opens up the three epistles. Anyone will be able to read, understand, and enjoy it.

There are a couple of volumes that look good, but for which I have not been able to find reviews. Philip Ryken’s 1 Timothy from the Reformed Expository Commentary series is bound to be good, as Ryken has a long track record as a skilled commentator. Bryan Chapell’s 1 and 2 Timothy and Titus from the Preaching the Word series would be similar in that it is a sermon-based commentary from a skilled preacher.

Dates

If it is true that Paul was released from prison (after the close of the book of Acts, possibly AD 59-61), then is there any early tradition of his post-prison activities (i.e. preaching in Spain, cf. Romans 15:24,28)? There are the pastoral Letters (cf. 2 Timothy 4:10) and 1 Clement 5. These suggest that Paul preached in the east and west (i.e. Spain) and was killed under "the prefects" (i.e. Tigellinus and Sabinus, who functioned in the last year of Nero's reign, A.D. 68). The Muratorian Fragment gives a list of canonical books from Rome about AD 180-200. Eusebius' Historical Ecclesiastical History 2:22:1-8, states that Paul was released from Roman imprisonment
It seems that 1 Timothy and Titus were written close together before Paul's re-arrest. 2 Timothy is Paul's last writing and good-bye while in prison.
Suggested dates therefore
 
1 Timothy – 62-63 AD
Titus – 62-63 AD
2 Timothy – 65-67 AD

1 Timothy 4:15 Full immersion

1 Timothy 4:15 Be diligent in these matters; give yourself wholly to them, so that everyone may see your progress.
These matters refers back to the call to Timothy to give himself to the public reading of Scripture and to preaching and pastoring and to verse 12 where he is told to be an example - in speech, in conduct, in love, in faith and in purity. He is now told that he must Be diligent in these matters. The AV has "meditate on" and the ESV "practice". These things must fill his mind and he must take care to do them. He must give himself wholly to them. He must keep on in them. Be fully immersed in them. It cannot be a hobby or pastime. Although he may only be reading Scripture and preaching only a short time each week and although all his direct pastoring may only amount to so many hours work, he is an example whenever he is seen and so must arrange his week that everything is geared to this programme and centred around these things. The reason Paul gives for this unified and highly focussed approach is so that everyone may see your progress. You see tour guides in London holding up an umbrella or a stick and leading their party. The people in the group know to go where the guide leads. Timothy is to lead the way like that. It is the task of all ministers to do the same.

1 Timothy 4:1 Demonic Teaching

1 Timothy 4:1 The Spirit clearly says that in later times some will abandon the faith and follow deceiving spirits and things taught by demons.
No doubt the later times that Paul talks about here refers to the whole period between the first and second coming of Christ. 2 Timothy 3:1ff says something similar (But mark this: there will be terrible times in the last days, etc). Quite how the Spirit has said clearly is not made set out but Paul is perhaps thinking of recorded Old Testament prophecies and ones from the New Testament period that have not all been recorded. Certainly Jesus himself said that At that time many will turn away from the faith and will betray and hate each other, etc (Matthew 24:10). The prophecy is that some will abandon the faith and that some will follow deceiving spirits and things taught by demons. Such information should give some comfort when we see apparent Christians apostatise and when we see large numbers of people believing things that run clean contrary to what God's Word teaches. Deceiving spirits are active and demons promulgate everything from the theory of evolution through the legitimacy of abortion and assisted suicide to the JW teaching against blood transfusions. Such wild ideas have been taught down the ages - the inferiority of certain races, the acceptability of bull or bear baiting, of human trafficking and crucifixion. This is what we must expect and not become alarmed at. It is part of a minister's calling to tell people that this is the case.

1 Timothy 3:8, 9, 12 Deacons Qualifications

1 Timothy 3:8, 9, 12 In the same way, deacons are to be worthy of respect, sincere, not indulging in much wine, and not pursuing dishonest gain.  They must keep hold of the deep truths of the faith with a clear conscience. .... A deacon must be faithful to his wife and must manage his children and his household well.
The seven main qualifications for a deacon (the Greek word simply means servant) are found in these verses. The In the same way at the beginning points to the fact that these qualifications are very similar to those for the elders. Both lists contain similar items - worthy of respect (respectable), not indulging in much wine (not given to drunkenness) and not pursuing dishonest gain (not a lover of money). Sincere appears and keeping hold of the deep truths of the faith with a clear conscience but not above reproachtemperate, self-controlled, hospitable, able to teach. Faithful to his wife and managing his children comes in verse 12. The deacon then has to be a mature believer but he may not have a gift to teach. His home life is again an important test of his ability in church life. Irreproachability and hospitableness are desirable but not of the essence of the work. We get a clear idea then of a New Testament deacon. One almost in every way like an elder but with a less public persona. If a church has faithful deacons getting on with the practical matters that always need to be thought of and so freeing the elders to do their real work then all the members will be greatly blessed indeed.

1 Timothy 3:2, 3 The Overseer

1 Timothy 3:2, 3 Now the overseer is to be above reproach, faithful to his wife, temperate, self-controlled, respectable, hospitable, able to teach, not given to drunkenness, not violent but gentle, not quarrelsome, not a lover of money.
These verses contain the basic qualifications for an overseer or elder. Some 11 characteristics are listed - the very number suggests, perhaps, someone above the average. The seventh qualification is different to all the others in that it does not necessarily have a moral dimension. This is the requirement that the overseer be able to teach. The other requirements would be desirable in all Christians. They are necessary for the teacher because without them his teaching will be hollow and hypocritical. So what is being looked for is an irreproachability, faithful monogamy, temperance, self-control, gravity, hospitableness, sobriety, gentleness, calmness and unselfishness. To be above reproach does not mean that a man is perfect but that there is no obvious flaw in his character and life. Some have assumed that an overseer must be married but the point is that he must be faithful to one wife if he is married. If she dies, he is not suddenly disqualified. The checklist serves both as  an indicator of what to look for in a possible overseer and as a reminder to overseers of what is required of them. If an elder finds he is becoming intemperate, say, or reclusive, violent, quarrelsome or is tempted to be unfaithful or get drunk or is lacking self control or thinking about money all the time then he is in serious trouble. He is no longer above reproach or respectable and is in danger of being unfit to teach.

1 Timothy 2:13, 14 Adam, Eve

1 Timothy 2:13, 14 For Adam was formed first, then Eve. And Adam was not the one deceived; it was the woman who was deceived and became a sinner.
In 1 Timothy 2:11, 12 Paul states plainly that though A woman should learn she should do so in quietness and full submission. Paul says I do not permit a woman to teach or to assume authority over a man; she must be quiet. He gives his arguments for this view in verses 13 and 14. His first argument is from creation and his second from the Fall. His first argument is from the very way God made man and woman in the first place. God could have made the woman first or the man and the woman at the same time but he did not. Rather, he deliberately, and Paul suggests pointedly, formed Adam first, and then Eve. Surely, says Paul there is something to learn from that very fact. It is a reminder to read our Bibles carefully. Secondly, reminding us of the Fall, he says And Adam was not the one deceived; it was the woman who was deceived and became a sinner. His point here seems to be that the Fall occurred only because basics like the precedence of man over woman were forgotten. When Eve took the lead she was deceived and so became the first sinner. Adam was not deceived though he still ate. Those who deny the Genesis account will, of course, struggle with Paul's reasoning here, but those who accept Genesis will also readily accept the rule that women should not be teachers or have authority over men in the church. This is an office reserved to men who God calls.

1 Timothy 2:3, 4 Pleasing God

1 Timothy 2:3, 4 This is good, and pleases God our Saviour, who wants all people to be saved and to come to a knowledge of the truth.
Having begun the chapter by urging prayer for all sorts of people Paul goes on to say why he is urging this activity and what it is in the character of God that lies behind this. So firstly he urges prayer for peace that leads to godliness because (forThis is good, and pleases God our Saviour. When peace prevails and godliness flourishes then that is good in itself, everybody benefits, and it is pleasing to God our Saviour. That is what he wants. In fact God wants all people to be saved and to come to a knowledge of the truth which no doubt means that God wants all sorts of people to be saved and to know the truth rather than that he wants every individual to be saved, which would surely contradict his purpose in election. Of course, there is a sense in which he does want all people to be saved as there is never any pleasure in God in the death of the wicked. It is interesting to note the way being saved and coming to a knowledge of the truth are linked here. They are clearly parallel. You cannot be saved without coming to a knowledge of the truth. Pastors must recognise what pleases God and so do all that they can to promote godliness. They must be concerned to see all sorts of people saved too, reaching out in many directions. They must also understand that it is as people get to know the truth that they are saved and so they will be preaching the truth at all times.

1 Timothy 1:20 Handed Over

1 Timothy 1:20 Among them are Hymenaeus and Alexander, whom I have handed over to Satan to be taught not to blaspheme.
In 1 Timothy 1:19 Paul talks about the way some have rejected faith and a good conscience and so have suffered shipwreck with regard to the faith. In verse 20 he gives the example of Hymenaeus and Alexander. A Hymenaeus (probably the same one) is mentioned in 2 Timothy 2:17 but we know nothing more about these two or what exactly happened but it is clear that whereas at one point they showed promise at a later point they, like Judas and Demas and others, became apostate. Paul says that he had handed them over to Satan, which is a phrase that Paul uses in 1 Corinthians 5 and is clearly a reference to church discipline. Paul did this with the hope that these blasphemers may be stopped. Whether Paul was hopeful of restoration or simply means that he was antiseptically removing the source of the blasphemy is not clear. What the verse reminds us is that people can become apostate, real people, people we know. It also makes clear that such people must be dealt with. They must be removed from the church so that they will not cause others to reject the faith and good conscience held out in the gospel. If such people are restored all to the good but if not at least the rot is stopped from spreading.

1 Timothy 1:7 Ignorant Bluffers

1 Timothy 1:7 They want to be teachers of the law, but they do not know what they are talking about or what they so confidently affirm.
Paul is talking to Timothy in this verse about the false teachers who he wants him to oppose. He points out the disconnect between their aspirations and the reality. They aspire to be teachers of the law. They want to be considered to be knowledgeable people, experts, those able to give instruction on matters of the law. In reality, they are ignorant and do not know what they are talking about or what they so confidently affirm. They are bluffers. They make out as if they are talking sense with their confident affirmations but the truth is that they have nothing of value to say. This is a phenomenon that is seen to this very day and that exists in many spheres. The first thing we must do, especially if we are preachers, is to make sure that we are not guilty of the same thing. Okay you want to be a minister, a pastor, an elder, a teacher. Nothing wrong with that. But do make sure that you know what you are talking about and that your emphatic assertions have real solidity. In order to do that there is need for time to study - study to prepare for the work in general and study to deliver the particular message at the time. Without that we will be subject to more and more people who may sound knowledgeable and who may speak reassuringly and yet who are ignorant bluffers. Where we see this in others we must do what we can to expose their ignorance and bluff in order that others will not be led astray.