In addition to being famous for constantly winning and being at the very top of the sport, Tiger Woods was also famous for something else – grinding out rounds when he didn’t have his best stuff. It’s an admirable trait for an all-time great who has accomplished enough in his career to take a round, or a shot, off if he felt like it. He almost never did.

While the refusal to quit was instilled in him from a young age, there was some other motivating factors for Woods during days where he wasn’t on his A game – not wanting to lose any of his own cash to his longtime caddie, Steve Williams. Williams, who joined us on a recent episode of The Loop podcast to discuss his new book “Together We Roared,” co-written with Evin Priest, says that when Woods would be hitting it all over the place, he found it useful to issue him a challenge in the form of friendly wagers.

 

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“When he’d get into a situation where things weren’t going well, I’d say ‘Okay, Tiger, in the next six holes, I’ll give you $100 for every fairway you hit and you give me $100 for every fairway you miss,” Williams said. “I’ll give you $100 for every green [in regulation] you hit and you’ll give me $100 for every green you miss. He hates to lose to anyone, but he hates to lose to me as well. And that would sometimes just make him — you think you’re playing in a golf tournament, obviously you’re trying as hard as you can, but that would just take away a little bit of the thought of not doing so well. 

“Those were the little bets we put in place because sometimes he’d turn things around because he just didn’t want to part with his money and give it to me.”

Williams told us a number of great stories, which are also featured in Together We Roared – a brilliant chronicle of his time on the 15-time major champion’s bag. Williams also described the generous side of Woods nobody talks about, the little notes Tiger would write him and the time he hung up on Woods multiple times thinking he was getting pranked.