Most caddies belong to one of two breeds: migrants or locals. The former follow the sun (and the cash); the latter remain rooted to a place and embody its spirit in their accents, their outlooks and their knowledge of the area. When Bart Ailstock walks up to you on the first tee of the Cascades Course at The Homestead and introduces himself in a backcountry Virginia drawl, you know which category he represents.
Ailstock, 62, has spent virtually all his life in and around the village of Hot Springs, home to this historic resort. His mother worked as a housekeeper for Sam Snead, and Ailstock was a hunting buddy of J. C. Snead, Sam’s nephew and fellow Tour pro. J. C. once challenged Ailstock to a match, giving him a stroke a hole. Ailstock bore down, prompting J. C. to say, “Boy, you’re taking it too seriously.” After seventeen holes they stood all square, just as darkness fell. “We hit off eighteen, and we found his ball, but we couldn’t find mine,” Ailstock recalls. “And that’s the way we ended up.”
To say Ailstock knows his way around the Cascades—one of the finest mountain courses in the country—is stating the obvious. He started toting bags there as a boy in the late 1950s. A carpenter by trade and part-time looper for decades, he began caddying full-time eight years ago, after one of his brothers died in a roofing accident and Ailstock decided he should do what he enjoys most. His course savvy comes in handy, such as on the fourth green, where seemingly sharp left-to-right putts barely break at all due to the mountain, and on the approach at twelve, where he advises taking an extra club because of a draft that stirs from an unseen gorge. Standing over your ball, you can’t feel the breeze, but sure enough, it’s there.
The Homestead, Cascades Course
1766 Homestead Drive, Hot Springs, Virginia.
William Flynn, 1923.