Joe Barreiro has been at Sleepy Hollow Country Club longer than many of the trees. The Ossining native started as a caddie in 1965. “I still remember my first loop,” he says with a smile. “It was for Mr. Robinson, and I got $5.50 plus a 50-cent tip because he said he enjoyed my company. That was big money then. You could go to the Victoria Theatre and see a movie with popcorn and a soda for 50 cents.”
Barreiro worked a couple of early years in the bag room then in 1973 took over his current position. Today, the venerable caddie master oversees about 85 caddies, although on any given day there will be about 30 on the job. They are pretty evenly split between high school and college kids, as well as many veterans.
One of the most satisfying parts of Barreiro’s job is introducing youngsters to the profession—and sometimes to the game itself. “I tell them right up front that they’re all on equal footing when they start, whether they play the game or not,” he explains. “We send them out with an experienced caddie anywhere from five to 10 times to learn the ropes. I also try to give the kids to members who enjoy working with them. Then the members give me feedback on how they did.”
Barreiro, 60, works seven days a week during the season—which for him stretches from March to December. His typical day at the peak of the season, from April through September, starts at 6:15 a.m. “It’s very rare that I’m not here until after sunset—which can be as late as 9:15 p.m.—for four or five months. It’s a long grind.”
Looking out over the Hudson from his station at the opulent Sleepy Hollow clubhouse, however, he adds, “What started as a job became a love affair.”