THEREFORE WHEN WE COULD ENDURE IT NO LONGER, WE THOUGHT IT BEST TO BE LEFT BEHIND AT ATHENS ALONE: Dio meketi stegontes (PAPMPN) eudokesamen (1PAAI) kataleiphthenai (APN) en Athenais monoi : (1Thes 3:5; 2:17; Jeremiah 20:9; 44:22; 2 Corinthians 2:13; 11:29,30) (Acts 17:15)

Paul had just explained his desire to see them but how Satan had thwarted him...

But we, brethren, having been bereft of you for a short while-- in person, not in spirit-- were all the more eager with great desire to see your face. For we wanted to come to you-- I, Paul, more than once-- and yet Satan thwarted us. (see notes 1Thessalonians 2:17; 18)

And what was the result of Satan's impeding Paul's personal return to Thessalonica? There were actually two results, one the letter we are reading today and second the sending and maturing of Timothy as a disciple maker in the lineage of his spiritual father Paul. What Satan meant for evil, God used for good, once again emphasizing His sovereignty over His creation including the fallen angels.

Therefore (1352)(dio) is a relatively emphatic marker of a result, usually denoting that the inference is self-evident. Synonyms include words or phrases like: so then; consequently, for this reason, on which account.

Therefore or on account of Paul's  affection for them (his "hope and joy and glory" 1Thes 2:19; 20), and the frustration of his attempts to return to them.

Lightfoot writes that therefore means...

on account of the very fervent desire, which I was unable to gratify

J Vernon McGee explains the therefore noting that...

this important word ties this chapter back in with what Paul had talked about in the previous chapter: the family relationship that exists in the church. He had been a mother to the church, a father to them, and a brother. He had led them to the Lord, and he loved them. He said that they would be his glory and his joy at the coming (parousia) of Christ, at the appearance of the Lord Jesus when all believers will receive their rewards.

Now because Paul had a real affection for them, he was frustrated in not being able to return to them. He had been hindered by Satan. Paul had to leave Thessalonica so quickly that there were many unfinished teachings and doctrines that he had not been able to develop fully. He not only longed to return, but he wondered about the future of the believers there. Paul desired to comfort them. In other words, he was demonstrating the thing he mentioned at the beginning of the letter—a labor of love.

Love is not affection or just a nice, comfortable, warm feeling around your heart. Love seeks the welfare of another. That is the way love is expressed for anyone. If you love someone, you seek his welfare and you actually would jeopardize your own life for the person whom you love. (McGee, J V: Thru the Bible Commentary:  Thomas Nelson or Logos)

We - In the present context Paul clearly states he was alone so his use of the plural pronoun here is what some refer to as an "editorial we". There are a few commentaries such as Hiebert which feel the "we" is used in the sense that all three missionaries shared these feelings and agreed to the plan of action to send Timothy.

Green agrees with Hiebert and has a reasonable explanation commenting that...

The verb we thought it best is the same as that found in 2.8, and the first person plural indicates that this decision was collective. If the plural is real and not editorial (we for “I”), the implication is that at some point Silvanus and Timothy traveled from Macedonia to Athens. Paul expresses his own, particular sentiments in v5, but the inclusion of this personal note does not negate the collective nature of the concern or the decision indicated in v1.  According to the narrative in Acts 17.14, Paul departed from Macedonia and traveled on to Athens, leaving Silvanus and Timothy in Berea. When he arrived, those who accompanied him went back to Macedonia “with instructions for Silas and Timothy to join him as soon as possible” (Acts 17.15). It appears that they did precisely this. After coming to Athens, Timothy was sent back to Thessalonica, at which time Paul and Silas were “left behind” in Athens. Silas himself returned to Macedonia as well, though this is not specifically mentioned but only implied from the Acts narrative. Paul left Athens and headed south to Corinth where Silas and Timothy caught up with him upon their return from Macedonia (Acts 18.1, 5). Acts does not include all the details of the comings and goings of several people who appear in the narrative, so the omission of some movements of the characters does not surprise us. (Pillar NT Commentary. Logos)

No longer (3371)(meketi from me = not + éti = anymore, yet, with k [kappa] inserted for phonics) means no more, no further, no longer. And in verse 5 Paul makes virtually the same statement but in that verse uses the singular pronoun "I".

Literally the Greek reads no longer forbearing.

Using the verb stego (see below) Paul is saying that his longing for personal communication and follow-up from his spiritual children had become intolerable.

Endure (4722)(stego from steg = to cover, conceal, stege = roof) had a fairly broad range of meanings including to cover, to protect, to hold back, to hide,  to bear,  to endure or to persist.

Stego means to protect by covering or  to cover closely (so as to keep water out). Thus stego is found in secular Greek writings - "the camp protects men against the cold" (Plato); "a house protects men".

Bruce explains that stego was used...

originally of keeping out or keeping in water or another fluid (e.g. of a watertight house or of a vessel that does not leak), comes from the latter sense to mean generally “to contain” and then “to endure” (Bruce, F F: 1 and 2 Thessalonians. Word Biblical Commentary. Dallas: Word, Incorporated. 1982 or Logos)

Stego can mean keep in in the sense of contain or conceal and may also be used as meaning to support that which is placed upon it, this latter sense being to hold out against or endure the pressure of circumstances. The Berkeley Translation thus renders it we could not "stand it any longer".

In this verse stego is in the present tense, denoting linear action, which as Hiebert explains...

indicates that they were unable to continue enduring the suspense that they felt because of the lack of personal communication with the Thessalonians. The continued separation from their beloved converts and the lack of information about their reaction under the pressure of persecution produced a strain of suspense that was unbearable. And there was ground for feeling anxious about their converts. If the unbelieving Jews were so relentless in their antagonism to the gospel as to hound the missionaries all the way to Berea, what might they be doing to their followers at home? The load of suspense was so heavy that they felt they had to take some action. (Hiebert, D. Edmond: 1 & 2 Thessalonians: BMH Book. 1996)

The related word steganos meant covering or sheltering (think about this as you study the use of stego in 1Corinthians 13:7 below).

Figuratively, stego derives it's meaning from the fact that by covering it keeps off something which threatens which then is taken to mean to bear up under.

At the core of its meaning stego denotes an activity or state which blocks entry from without or exit from within. Hence to protect by covering, as with a tight ship or roof.

The depth of the emotion expressed by the principal verb is illustrated in a papyrus that says

For my father did many evil things to me, and I bore them until you came (Moulton and Milligan)

Vine writes that stego...

signifies either that of which it is predicated supports what is placed upon it or covers what is placed underneath it. The former idea is prominent here and in 1Thessalonians 3:5  (Vine, W. Collected writings of W. E. Vine. Nashville: Thomas Nelson or Logos)

TDNT has a somewhat more technical note based on use in secular and classic Greek literature...

The tendency of Greek. towards linguistic ambivalence helps us to see why stego can have an outward as well as an inward reference and mean not only “to protect” but also “to ward off,” “to hold back.” Domos ala stegon is a structure which holds off the salt floods, namely, a ship... The sense “to hold back” leads to that of “make tight” of a ship; “to make something watertight,”; finally “to be watertight” (“ships which are not watertight”) and “to hold fast,” “to hold”. The sense “to ward off,” “to protect,” seems to be the starting point for the further meanings “to endure,” “to support,” “to bear.” A tower which has resisted the assault on a city has endured it (Aeschylus). How this can lead to “bear” in the technical sense may be seen from Josephus Ant., 5, 314: "pillars which endure the weight of the roof bear it... The figurative power of the word helps us to understand why even the oldest witnesses use it in a transferred sense. Thus it means “to cover, conceal” an intellectual matter, Eur. Phoen., 1214, “to hide,” Sophocles Trach..., “to withhold” a judgment, Polyb., 4, 8, 2 and then especially “to keep silent”: Phil., 136, cf. Oed. Tyr., 341; Eur. El., 273; Polyb., 8; 14, 5; Jos. Ant., 19, 48, and the one LXX ref. at Sir. 8:17: logon stegein = “to keep a confidence.” With the silence complex, the main transferred use of stego is "to bear" (eg, the stench of an ulcer)...

At the core of its meaning stego denotes an activity or state which blocks entry from without or exit from within.  It is not inwardly related to any particular subj. or obj. and refers to the hampering of ingress or egress, so that it may be used either of material or intellectual things: “to cover,” “to conceal,” with a ref. later to the function of that which separates: “to be compact, watertight,” “to bear,” “to sustain.”...

(relating to the use in 1Thessalonians) Paul, impelled by his missionary task, can no longer bear not to have an influence on the development of the young church in Thessalonica. (Kittel, G., Friedrich, G., & Bromiley, G. W.  Theological Dictionary of the New Testament. Eerdmans)

Aeschylus describes a ship...

The wooden house with sails that keeps (stego) out the sea.

In the present verse stego means to endure patiently, to forbear, to suffer.

There are 4 uses of stego in the NT (none in the Septuagint - LXX)...

1 Corinthians 9:12 (Context = In the preceding 11 verses Paul emphasizes that he has the same right as other apostles to eat and drink, to take a wife with him, and to live by his missionary labours) If others share the right over you, do we not more? Nevertheless, we did not use this right, but we endure (stego - bear or suffer) all things, that we may cause no hindrance to the gospel of Christ. (Comment: Using the verb stego here Paul is saying in essence "we refrain from all that pertains to the legitimate private sphere of an apostle in order not to give an offense to the Gospel which belongs to Christ")

1 Corinthians 13:7 bears (Stego - Love endures without divulging to the world personal distress. Literally said of holding fast like a watertight vessel; so the charitable man contains himself in silence from giving vent to what selfishness would prompt under personal hardship. Moffatt translates it "slow to expose") all things, believes all things, hopes all things, endures all things. (Comment: John MacArthur has an excellent note to help discern the meaning...

Stego (to bear) basically means to cover or to support and therefore to protect. Love bears all things by protecting others from exposure, ridicule, or harm. Genuine love does not gossip or listen to gossip. Even when a sin is certain, love tries to correct it with the least possible hurt and harm to the guilty person. Love never protects sin but is anxious to protect the sinner. Fallen human nature has the opposite inclination. There is perverse pleasure in exposing someone’s faults and failures. As already mentioned, that is what makes gossip appealing. The Corinthians cared little for the feelings or welfare of fellow believers. It was every person for himself. Like the Pharisees, they paid little attention to others, except when those others were failing or sinning. Man’s depravity causes him to rejoice in the depravity of others. It is that depraved pleasure that sells magazines and newspapers that cater to exposes, “true confessions,” and the like. It is the same sort of pleasure that makes children tattle on brothers and sisters. Whether to feel self–righteous by exposing another’s sin or to enjoy that sin vicariously, we all are tempted to take a certain kind of pleasure in the sins of others. Love has no part in that. It does not expose or exploit, gloat or condemn. It bears; it does not bare. [He goes on to illustrate this covering, protecting aspect of stego] During Oliver Cromwell’s reign as lord protector of England a young soldier was sentenced to die. The girl to whom he was engaged pleaded with Cromwell to spare the life of her beloved, but to no avail. The young man was to be executed when the curfew bell sounded, but when the sexton repeatedly pulled the rope the bell made no sound. The girl had climbed into the belfry and wrapped herself around the clapper so that it could not strike the bell. Her body was smashed and bruised, but she did not let go until the clapper stopped swinging. She managed to climb down, bruised and bleeding, to meet those awaiting the execution. When she explained what she had done, Cromwell commuted the sentence. A poet beautifully recorded the story as follows:

At his feet she told her story,
showed her hands all bruised and torn,
And her sweet young face still haggard
with the anguish it had worn,
Touched his heart with sudden pity,
lit his eyes with misty light.
"Go, your lover lives,” said Cromwell;
"Curfew will not ring tonight."

(MacArthur, J: 1Corinthians. Chicago: Moody Press or Logos)

1 Thessalonians 3:1 Therefore when we could endure it no longer, we thought it best to be left behind at Athens alone

1Thessalonians 3:5 (note) For this reason, when I could endure it no longer, I also sent to find out about your faith, for fear that the tempter might have tempted you, and our labor should be in vain.

Vine feels that Paul's...

mingled hope, 1Thessalonians 2:17 (note), and fear, 1Thessalonians 3:5 (note), imposed a strain in the mind of the apostle for which he sought relief in the manner described. (Vine, W. Collected writings of W. E. Vine. Nashville: Thomas Nelson or Logos)

Thought best (considered it good, willingly determined, was well pleased) (2106)(eudokeo from eu = well + dokeo = think) means to think well of, be well pleased, to approve of or to take pleasure or delight in (As God does in His only Son Mt 3:17 This is My beloved Son in Whom I am well pleased)

Eudokeo denotes not merely to think good of something but also stresses free and deliberate choice, the freedom of a resolve in what is good.

Eudokeo conveys a strong element of emotional satisfaction and delight.

The aorist tense expresses a definitive determination made and adhered to. It was the free and deliberate choice for Paul to stay and Timothy to go. (“we were pleased and resolved”). Thus the plan was accepted with hearty goodwill. Paul considered it good and therefore worthy of choice to be left behind. He resolved or determined to be left behind. He says in essence...

I was willing to suffer the inconvenience of parting with Timothy in order to show my concern for you.

Keathley adds that...

eudokeo means “to be well pleased, to willingly determine, to think it a good thing to do.” It stresses the willingness, the positive choice. Too often, ministry is performed out of a sense of, “Well, if I have to.” The option the missionary team chose was not done grudgingly. (1Thessalonians 3:1-13 )

Left behind (2641)(kataleipo from kata = intensifies meaning + leipo = leave behind) signifies to leave behind, to leave remaining, to forsake in the sense of abandoning. It means to cause to be left in a place.

Paul use the passive voice in this verse which means to “be left alone or behind" or "to be forsaken.”

The word kataleipo  was used in secular Greek to describe the leaving of a loved one behind at death and clearly expresses how serious Paul took his separation from his coworkers.

 Hiebert adds that kataleipo...

implies the feeling of loneliness and desolation that swept over him when left all alone in Athens.  ((Hiebert, D. Edmond: 1 & 2 Thessalonians: BMH Book. 1996))

Paul's strong affection for the young church in Thessalonica is shown here by his selflessness and willingness to be left alone in Athens. Paul, Silvanus and Timothy did not love the church only when they were face to face with them. They carried these believers in their hearts (see note 1Thessalonians 2:17).

Ray Stedman in a personal anecdote gives us a sense of how the apostle Paul may have felt as he was left alone...

In 1960 I spent the summer in the Orient. In company with Dr. Dick Hillis I was scheduled to speak to six hundred Chinese pastors on the island of Taiwan. This was a difficult assignment as my messages were to be interpreted into two different languages, Mandarin and Taiwanese. It is hard enough speaking through one "interrupter," but with two, by the time one sentence has been interpreted you have forgotten what you just said. But I was comforted by the fact that Dick Hillis, a veteran missionary, was with me. The day before I was due to speak, however, he got a telegram saying that his mother was ill in California and he had to return home. I have never forgotten the depression and loneliness that came over me. I am sure that is how Paul must have felt as he was left alone in Corinth, that cultured, degraded center of Roman life. (1Thessalonians 3:1-3:13)

Alone (3441) (monos) means without others or without companions. It indicates Paul was not just left behind but left behind by himself as emphasized by Luke's record that...

those who conducted Paul brought him as far as Athens; and receiving a command for Silas and Timothy to come to him as soon as possible, they departed. (Acts 17:15)

Athens (116)(athenai) is named after Athena, the Greek goddess of wisdom, arts, and industries and prudent warfare, identified by the Romans with Minerva. After the Roman conquest, Athens (pl.) became a federated city entirely independent of the governor of Achaia, who paid no taxes to Rome and had internal judicial autonomy. Athenians were said to possess the keenest minds among the Greeks, and the University of Athens was the most important school, ahead of those of Tarsus and Alexandria. The Athenians were religious but not spiritual and indulged in lasciviousness at the festival of Dionysus, the god of wine. They had great love of human slaughter in the gladiatorial games.

Imagine Paul alone in a huge metropolis, in fact in the ancient world one of the major centers of blatant idolatry!

Paul was a man on mission. He was not on a sight seeing trip, but was burdened for the "church plant" in Thessalonica. Paul continually viewed this present life through the lens of eternity.