"Whenever he saw a dollar in another man's hands he took it as a personal grudge, if he couldn't take it any other way"

O. Henry’s remark describes a character whose relationship with money is deeply personal and adversarial. The observation suggests that for this individual, the existence of wealth in someone else’s possession provokes not just envy, but animosity, a sense of being wronged simply because another possesses what he does not. The language implies a pathological competitiveness, where monetary gain becomes a zero-sum game, and every dollar not in his own pocket is interpreted as an affront or loss.

This perspective reveals a man who is not merely greedy or acquisitive, but whose sense of self-worth and security is threatened by others’ prosperity. Such a person may be driven by insecurity or resentment, feeling diminished in status each time he witnesses another man’s financial success. The phrase "took it as a personal grudge" dramatizes the emotional weight attached to money: he perceives wealth in the hands of others almost as a theft from himself, regardless of any real transgression.

Furthermore, the latter part, "if he couldn't take it any other way", suggests a kind of moral or practical flexibility in his pursuit of riches. The character is not above taking money through whatever means are available, potentially even through unethical or forceful tactics. If he is unable to acquire it legitimately, his feelings of resentment may escalate, framing his failure not as the result of fair competition, but as a personal injustice. It positions him as fundamentally antagonistic, locked in endless conflict with those around him, always measuring his fortunes against theirs.

This attitude ultimately isolates him, trapping him in a perpetual sense of grievance. O. Henry’s portrayal offers a sharp critique of materialism and the corrosive effects that unchecked envy and possessiveness can have on one’s character and relationships. The pursuit of wealth becomes not just an ambition, but a corrosive obsession.