In June 2019, Brennan Little was on the bag for Gary Woodland for an outstanding U.S. Open victory at Pebble Beach. As they get set to defend this week at Winged Foot in New York, we sat down for a chat with Little — now a two-time major winning caddie. Little also spent years caddying for Canada’s Mike Weir — a childhood friend — and was alongside him for a victory in the 2003 Masters. We talked to Little about his 2+ decades as a caddie, his own professional career, staying at the home of childhood hero Wayne Gretzky and a whole lot more.
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