Happiest caddie at Augusta: Esteban Toledo realizes his Masters ‘dream’

For 27 years, boxer-turned-golfer Esteban Toledo dreamed about playing in the Masters. “I watch every minute of it over and over, like a little kid,” he said, sharing the sentiment of so many of us.

Toledo finished second twice during his eight seasons on the PGA Tour, but close doesn’t count when it comes to invites to the Masters. Toledo, 53, won’t play in this year’s Masters, but he will be inside the ropes: as a caddie for 1988 champion Sandy Lyle.

“Isn’t it cool? I can’t wait,” Toledo said. “It’s going to be a dream that you don’t want to wake from.”

How does a four-time PGA Tour Champions winner end up in white Masters coveralls? This story begins a little more than a year ago, when Toledo conceived the idea and asked Ben Crenshaw to caddie for him at Augusta National. But the two-time Masters champion already had set in motion plans to take one final stroll down memory lane with his longtime Masters bagman, Carl Jackson.

“I guess Sandy was listening to that whole conversation. So I asked him. He already had a caddie too. He said, ‘Maybe another time,’ ” said Toledo, who responded, “Man, I want to get in. Before I die, I want to experience Augusta.”

Days after Toledo won the Allianz Championship in February, he and Lyle were practicing when he broached the subject again. “I said, ‘Hey, Sandy, am I going to caddie for you or what?’ I was joking around. His wife has been caddieing for him, and he looked at me and said, ‘Are you serious?’ I said, ‘Yeah.’ Sandy didn’t believe me, so he asked my caddie, who said, ‘I think so. He just wants to see what it will be like one time in his life.’ ”

A month passed, and then Lyle’s wife, Jolande, called Toledo from Scotland. She told him, “You’re on.”

“I said, ‘Are you kidding me?’ I’m like a kid in a candy store,” Toledo said. “I’m a four-time winner on the Champions Tour, but I don’t care. I’m not a big shot. I’m caddieing for a guy who’s won a Masters.”

Calling it his “Masters surprise,” Lyle tweeted, “May his recent win @AllianzChamp rub off on me.”

But looping at the Masters is only half of this story. Toledo’s dream of playing at Augusta came true, too.

Over the years, he had asked so many members whether they could get him on the fabled course designed by Alister MacKenzie and Bobby Jones that he lost count. But that changed last summer when Toledo won The First Tee Open at Pebble Beach. He met Peter Ueberroth, the former Major League Baseball commissioner and a part-owner of Pebble Beach, who asked Toledo to name the best course he’d ever played. Recalling the scene, Toledo said, “I told him Pebble Beach, but I’d never played Augusta. He said he knew some members. I thought, ‘Yeah, like everybody else.’ He called me up and said it was all arranged. I was shocked.”

That’s how Toledo found himself living out his dream of playing Augusta National in November.

“Toby Wilt (the starter at the Masters) hosted me,” Toledo said. “I was so nervous when we played that first hole. It was raining and he asked, ‘Are you sure you want to play in the rain?’ I said, ‘I have been waiting 27 years. I am playing no matter what,’ and I got my dream to play Augusta at least once in my life, and it was the most beautiful thing I’d ever seen. I walked over the Hogan Bridge and took my picture at No. 12.”

Toledo hung the memento in his office next to a picture he once took with Tiger Woods.

“I asked Fred Couples what to do, and he said, ‘Play from the members’ tee. You will enjoy it.’ I think I shot 2 under the first time. The second time I made 11 birdies in two days,” Toledo said. “I had so much fun.”

That’s right. There was a second time. Jimmy Dunne III, who heads Wall Street investment firm Sandler O’Neil & Partners, hosted a return trip Nov. 21. And now Toledo, who learned the game as a caddie at Mexicali Country Club in his native Mexico and boxed before becoming a golf pro, is set to experience the April 7-10 Masters from inside the ropes in what he calls the next-best thing to his dream of playing in the Masters.

“I’m not going to charge Sandy anything, because he is my friend. I’m not doing it for the money,” Toledo said. “I’m a former caddie, and I know the job description is ‘Show up, keep up, shut up.’ But I’m not going to shut up. I’m going to push him all the way. I know he is a fighter, and I’m the same way.”