We read in Acts 20:3 that the Jews made a plot against Paul when he was about to set sail for Syria. I will argue that the plot is historical and that it consisted of the decision by the Jews to intercept Paul if he attempted to deliver the collection. Points 3, 4, 5, and 8, are new.
1. Paul nowhere identifies anyone who helped with the collection. The two 'brothers' in 2 Cor 8:18-24 and the 'brother' of 2 Cor 12:18 are strangely anonymous, and Paul conspicuously uses Timothy's lesser-known name (Titus) when discussing him in connection to his missions to organize the collection. These silences are explicable if Paul was aware of opposition to the collection and was worried that it would be endangered if the identities of the helpers would leak out.
2. The plot was when Paul was about to sail. This is historically plausible since only at that time would it have been possible for the Jews to attempt to intercept the collection. Before that time the collection was dispersed in the homes of the individual donors (see 1 Cor 16:2).
3. If the plot was to attack Paul's person, it is surprising that he found out about it. If, on the other hand, Paul had been publicly forbidden from delivering the collection, he would have had reason to suspect that he would be under surveillance. Paul's knowledge of the "plot" is then explicable.
4. If the Jews (who had been given jurisdiction by Gallio) had declared the collection illegal, it would have been too dangerous for Paul to return to the Aegean after delivering the collection, and this would explain why Paul knew that he would not see the Ephesians again (Acts 20:25). The collection's illegality also explains why Acts does not mention it (for Luke is always careful to avoid giving any hint that the Christians do anything illegal).
5. We read that to avoid the plot Paul went north to Macedonia (Acts 20:3) and he sailed from Philippi and stayed in Troas (Acts 20:5). Why Philippi and Troas, rather than, for example, Beroea, Thesssalonica, or Ephesus? This was a long diversion, given his tight schedule (Acts 20:16). Well, it occurs to me that Philippi and Troas are the cities where he would have been safest from the plot of the Jews. We have no evidence of a synagogue in Philippi, and Acts records no Jewish opposition to Paul there. Also, there is no evidence that there were Jews in Troas in the first century.
6. Jewett argues that the boat that Paul took from Philippi to Patara was probably a coastal freighter that he had obtained for his exclusive use. This would have avoided the risk of being betrayed by fellow-passengers or port officials.
7. Paul's decision to split the party (Acts 20:5) will have served to protect the collection (so Gilchrist). The delegates (who were not under suspicion) would have been able to carry the collection with little risk of ambush, while Paul and Luke travelled separately with their empty pockets hanging out. Paul also travelled independently to Assos (Acts 20:13-14) and this also makes sense as a precaution against being arrested or ambushed while boarding a boat with the collection.
8. At first sight it seems that this "we" passage gives a surprisingly detailed and boring account of the journey. However, if the intended readers were expected to know that Paul was in danger of arrest or ambush, this passage is a gripping account of a daring escape and its inclusion is explicable.
It seems to me that the contents of this "We passage" comport well with the preceding mention of the plot (Acts 20:3). It is hard to imagine that Luke has inserted someone else's travel diary into his text at this point, as many suppose.
In summary: Paul, knowing that the collection would be opposed by synagogue Jews, chose to protect the identities of those who were to deliver it. The Jews in Achaia forbid Paul from delivering the collection, but he chose to do so anyway, even though he knew that he would be arrested if he ever returned to the Aegean. He was aware that he was under suspicion and that if he took a boat heading east he could be betrayed by crew or fellow passengers. He therefore headed north to Philippi, where there were few, if any, Jews who opposed him. Knowing that he was under more suspicion than the delegates, he sent them ahead to Troas with the money. Later, he walked from Troas to Assos, as a diversionary tactic, while the others took the money in the boat. To avoid being betrayed by fellow passengers they chartered a coastal freighter for their private use. Luke did not want to mention the collection in writing because of its illegality (Acts might fall into the hands of opponents), but his intended readers probably already knew about it. He wrote a dramatic account of how he and the others smuggled the collection out of the Aegean.
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