At the beginning of "Winter Dreams," when Dexter is fourteen years old, Mr. T.A. Hedrick is one of the rich Sherry Island Golf Club members who he dreams of defeating as he waits for the Minnesota winter to end.
Long after Dexter has quit his caddying job, once he has started making some money on his own, he does play golf with this guy. But we never find out if Dexter actually defeats him (though his chances are good, since Mr. T.A. Hedrick is "a bore and not even a good golfer any more" [2.5]).
Here's where it get's interesting. A golf ball comes flying out to hit Mr. T.A. Hedrick in the stomach around the fifteenth hole. Who is it that hit this ball? None other than Judy Jones. If it weren't for Hedrick's stomach, maybe Dexter and Judy would not have met a second time.
Judy shows basically no remorse about hitting Mr. Hedrick (what a surprise). In fact, she reports to her golfing partner that she hit something, rather than someone. Hedrick is understandably cheesed off about Judy's lack of concern. He badmouths her pretty severely, saying that she needs to "be turned up and spanked for six months and then to be married off to an old-fashioned cavalry captain" (2.18). The fact that Mr. T.A. Hedrick is not sensitive to Judy's charms is a sign of how old he is. If he were young, like Dexter or Mr. Sandwood, he might have accepted that ball to the stomach willingly, if it got him the chance to talk to Judy.