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With Jackson on the bag, Crenshaw was a perennial contender at Augusta National through the prime of his career, winning his first green jacket in 1984 and posting nine other top-10 finishes over a 16-year period.
"A lot of near misses, and some really fun times, and some painful times as well," Crenshaw said.
Then, with his career in a downward spiral and mourning the death of mentor Harvey Penick, Crenshaw teamed with Jackson for his most memorable triumph in 1995. A tip from the caddie helped Crenshaw get his swing straightened out on the practice range. After returning from Penick's funeral, Crenshaw put together three straight rounds in the 60s to beat Davis Love III by a single stroke.
The picture of Crenshaw -- bent over and crying his eyes out on the 18th green, Jackson having walked up from behind to put his two large hands gently on the player's shoulders -- remains one of the most memorable in Masters history.
"It just happened," Jackson said. "I was going somewhere else, and something changed my mind. I turned around and there was Ben, boohooing."
These days, Jackson runs a caddie program at the Alotian Golf Club near Little Rock, Ark., hoping to lure people of color into the sport.
He was a pretty good golfer in his day, getting his handicap into the single digits. He might've made it to the Tour himself with the right instruction and access to the best courses, and he certainly knows of other African-Americans who were even more skilled but never got the chance to advance beyond the caddie ranks.
Times have changed, of course. Augusta National has black members. Tiger Woods has won 14 major titles. The days of being forced to use club caddies ended nearly three decades ago.
But there are still few African-Americans in the golf pipeline, something that Jackson hopes to change. The first rule of being a good caddie, he says, is being a good golfer.
"If you're going to make suggestions, you've got to have an understanding of what you're trying to suggest," he said. "I can't see myself making a suggestion to a surgeon."
Jackson wants to help ensure the next Tiger Woods doesn't fall through the cracks.
He can think of no better way to honor those who came before him, like Pappy and Iron Man.
"They just adopted me," Jackson said. "They thought I had some instincts for the game, and they helped me bring them out. Those are the guys who did it."
[Associated Press;
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