From First Corinthians by George T. Montague, SM, commenting on I Corinthians 1:22-25
The tendency of the Jews who opposed the ministry of Jesus and that of Paul (compare Matt 12:38–42; Luke 11:29–32), was to demand signs, miracles or spectacular deeds of power, and Greeks look for wisdom, something that will captivate but not disturb the cultured mind.
Paul here shows his grasp of the psychology of both cultures, which made him an apt instrument for reaching both, but he does so by proclaiming something that goes counter to, because it goes beyond, the natural tastes of each: Christ crucified.
Jews indeed looked for a Messiah, but the fact that Jesus died on the cross proved that he was not the glorious liberator they desired. For them, the cross was a stumbling block, an obstacle to faith.
The Greek understanding of time and history was not eschatological: it did not have a conception of a goal toward which history was moving. “Time,” Aristotle said, “is a kind of circle.” Thus a religious founder should be one who more than any other would lead one to contemplate the order and harmony of the universe and lead humanity to a more harmonious subjection to its inevitability.
This was at least the view of the Stoics, who were Paul’s contemporaries and with whom he argued in Athens (Acts 17:18). In short, such a founder should be a philosopher. A founder who stands the world’s values on its head by going to death on a cross—the fate of the criminal dregs of humanity—would indeed have no chance of winning the Greek, even less by claiming that the cross was followed by the resurrection of the body.
As for the Jewish critic, the apparent failure of one who claimed to be the Messiah was proof that he was not. That is why it takes a special grace, a divine call, to read in the cross more than stupidity and weakness.