Not to get completely off topic here, but if you enjoy reading, check out 'Sir Walter' by Tom Clavin. I'm only a chapter or two away from finishing my second reading of the book about 'The Haig.'
Hagen was definitely a hustler, ranking right up there with Titanic Thompson and Ky Laffoon back in that era. Hagen was known for showing up late for his morning tee time, be it an exhibition match or a tournament round. 'The Haig' loved the nightlife, drank and caroused into the wee hours of the night, had no bearings for punctuality. But despite all of his off-course shenanigans, he was still one of the greatest golfers of his era (perhaps the greatest, up until Bobby Jones arrived on the scene). And even then - Bobby Jones conceded that Walter was a phenomenal player, after a series of exhibitions against him in which the Haig got the better of him quite often. Jones, obviously, was an amateur and the substantial exhibition purses weren't exactly a motivating factor for Jones, since he couldn't accept the payout because of his amateur status.
It's worth noting that Hagen's career started in 1912, and spanned through both the Great Depression and WW2. Although the money he earned through pro golf insulated him from financial burdens during these periods, it's still a testament to how good he was, how much he hustled, and how much money he made during that period through both PGA sanctioned events and exhibition matches. He was basically nearing the sunset of his career when Sam Snead came on tour, but had spent the latter half of his career competing against Gene Sarazen (20's and 30's). In fact... if what Clavin writes is correct - Sarazen's "shot heard 'round the world" (the albatross on the 15th at Augusta courtesy of a 4-wood) happened with Walter playing alongside him in the Masters tournament back in 1935. The Haig and The Squire had quite the rivalry going for a few years during that time, but both were close friends beyond the ropes.
Anyway.... one of the more memorable stories from Clavin's book happened one evening at Oakland Hills. Hagen and his gathering at the club's bar drank and partied until midnight. Then Hagen offered a wager, that he could make par on the club's toughest hole - the par4 10th, in complete darkness. The money started flying... the members there couldn't believe what they were hearing, and were more than ready to take on the odds. Hagen grabbed his clubs and quickly raced down to the nearby 10th tee, in complete darkness, with the large audience following behind, with torches in hand so they could see. Hagen told them that he was going to hit his tee shot in the fairway, just short of the bunker. He took a mighty swing, and then they were off. Sure enough - they spotted a ball on the left side of the fairway just short of the bunker, like he'd said. Then prior to hitting his approach, he told them his ball would end up on the green and 10 feet away from the hole. He took another swing and off they went to the green, only to find a ball pin-high and 10 feet away. He coaxed the 10 footer to the hole, then tapped in for his par, pocketing several hundred dollars in wagers along the way.
Later on it was revealed that Hagen had planned this miraculous midnight feat all along, paying a course staff worker well ahead of time to plant a ball in the fairway right where he wanted it, and then to place another one 10 feet from the hole.
Of course, he bought drinks for everyone afterward....
But that was a huge part of Walter's mystique. Great golfer, but an even greater hustler.
Great book, by the way, if you ever get a chance to read it and are interested. The sport we love is full of colorful characters and great stories.