The journey of Tiger Woods’ first Masters caddie, Tommy Bennett


Tommy Bennett did not want to caddie for Tiger Woods at the 1995 Masters.

“I didn’t want no damn amateur,” he recalls. “I wanted that green jacket.”

He wanted to carry for Dicky Pride, a promising young pro who had won a PGA Tour event the previous summer in Memphis, Tennessee. But Pride’s sponsor preferred a different man on his bag, and so did Jack Stephens, the investment banking magnate who was the chair of Augusta National Golf Club. Twenty years after Lee Elder had become the first African American invited to play the Masters, and five years after the club had accepted its first African-American member, Stephens knew that Woods was primed to become the game’s first Black megastar. Like Earl Woods, Tiger’s father, and Butch Harmon, Tiger’s coach, Stephens wanted to assign the rookie a tour caddie who knew his way around.

Though the unassuming Stephens was not quite as autocratic as some Augusta National overlords — Bennett calls him one of the nicest men he’s ever carried for — the chair could drop the hammer on club employees when he deemed it necessary.

“You can caddie for Tiger Woods or nobody at all,” he told Bennett.

The 45-year-old veteran didn’t need much time to weigh his options.

“I went with Tiger,” he says.

Today Bennett is 71, with a friendly, youthful face behind a salt-and-pepper mustache. He maintains a trim build by caddying at Sage Valley in Graniteville, South Carolina, just outside of Augusta, and occasionally on the Korn Ferry Tour. He still plays golf at the hardscrabble Augusta Municipal Golf Course (also known as the Patch), skins games with his old friends, many of them fellow Black caddies from the days when Augusta National was segregated; all its caddies were Black and all its members were white. Bennett started working at the National in 1964, when he earned $11 looping for Nashville billionaire E. Bronson Ingram II, and stopped in 1997 after, he says, he was fired by the club’s caddie management and training service for showing up late for work. “They told me my attitude was bad and they didn’t need me anymore,” Bennett says. (The club said it does not comment on personnel matters.) He cleaned out his locker and hasn’t been back since.

But Bennett remains an irreplaceable part of Woods’ Augusta National journey. He had actually met young Tiger before 1995, in passing (literally and figuratively), during a practice round at the 1993 Byron Nelson Classic. The caddie was working for a player named JC Anderson, who was chipping and putting on the 16th hole when Bennett saw a 17-year-old Woods and his father approaching from the fairway. Team Tiger wanted to play through.

“So we said, ‘Come on through,'” Bennett recalls. “And Tiger was like, ‘Why don’t you get out of the way?’ I’m like, ‘Damn, man, come on through, it’s a practice round.’ He rolled his eyes at me, and I rolled my eyes at him. F—in’ kid.”

On the Sunday before the ’95 Masters, Bennett walked and talked and lunched with Earl Woods. Earl, a 63-year-old smoker, had considered caddying for his son before deciding he couldn’t handle the hills. Tiger’s father told Bennett his work would be evaluated during the week, suggesting he could get pulled before Thursday’s start. The caddie was hardly thrilled to hear that.

Monday morning, Tiger and Tommy got together at the Augusta National practice range. Woods had emerged from the Crow’s Nest, the dorm-style suite for amateurs in the clubhouse’s attic, and was busy hitting balls on the range when the man he had (briefly) met at the Byron Nelson walked up to him with the offer of a handshake.

“I said, ‘Tiger Woods, Tommy Bennett, I’m your caddie,'” Bennett says. Tiger’s reaction told Bennett there was no doubt that he remembered their previous encounter. The caddie makes circles with his forefingers and thumbs and says, “His eyes got that big.” Woods did not bring up the ’93 Nelson. He just hit more balls before heading off with his unlikely caddie to begin the first week of the rest of his life.

A quarter century later, Woods returns to Augusta National as a five-time Masters winner and a defending champ who was forced by the pandemic to wait 19 months to try to match Jack Nicklaus’ record of six green jackets. Woods will be joined by his caddie, Joe LaCava, who was there for that memorable embrace in 2019, just like Steve Williams was there for Tiger’s three previous Masters victories, and just like Mike “Fluff” Cowan was there for the dominant breakthrough in 1997, two years after Tiger debuted as a gangly Stanford freshman who needed all the local knowledge Tommy Bennett of Augusta, Georgia, could give him.

Tommy grew up with his two younger sisters in Augusta’s Sand Hills neighborhood, which, according to the National Park Service, became home to Black laborers and domestic servants after the Civil War. Many Sand Hills residents worked for the wealthy white families in adjacent Summerville, for the members at Augusta Country Club and for the captains of industry prominent enough to belong to Augusta National, after it was built in the early 1930s.

Tommy never knew his father, and his mother worked as a housekeeper in New York. His grandmother, Easter, helped raise Tommy and his sisters in a one-bedroom shotgun house on the narrow lots of Sand Hills, which rested on the southern border of the country club and 3 miles south of the National. When he was 5 or 6 years old, Tommy tried to use a stepladder to steal some biscuits his grandmother was baking on their wood stove. He slipped and badly scalded his left leg, landing him in the hospital for nearly a month and, ultimately, earning him one of the finest caddie nicknames of all: Burnt Biscuits.

As a child, Tommy was already cutting wood before school for the morning fire. In 1959, he started carrying golf clubs, or trying to, when he was a 90-pound 10-year-old and a Mr. Slaughter (“I’ll never forget that name,” Bennett says) asked him to go nine holes at Augusta Country Club. After five holes, an exhausted Tommy threw in the towel. Mr. Slaughter, he recalls, “ended up carrying me and the bag.”

Caddying was a big deal in Sand Hills, where revenue streams were in short supply. Jim Dent, the one successful professional player from the neighborhood, started out with other people’s bags on his shoulders. Tommy used to earn a dollar picking up balls for Dent. During Masters week, he would admire the neighborhood men dressed in their white jumpsuits, signaling their role in the world’s most prestigious golf tournament. Like everyone else, Tommy started out at the country club making three or four bucks a loop, until he was good enough and experienced enough to graduate to the big leagues at the National.

Bennett was only 15 when he was deemed ready to make his Masters debut in 1965 with A. Downing Gray, at the time one of the nation’s premier amateurs. Tommy was nervous on the first tee Thursday morning at 9:30; they were paired with the legendary Gene Sarazen, 63. He was more nervous on the first green, when Gray surprised him by asking him to take a look at his 18-foot putt. “He hadn’t asked me anything all week,” Bennett says. Gray missed the putt, barely, but kept complimenting the teenager on his read, calming him down.

Tommy had designs on attending college, but he got his girlfriend pregnant and dropped out of high school after 11th grade. “It really changed my life a lot,” Bennett recalls. “I was a kid, and now I had to be an adult to support a child.” His options were limited in the Jim Crow South. At the National, however, Bennett could find steady work. As Clifford Roberts, the Wall Street financier who co-founded the club with Bobby Jones in 1932, once reportedly said, “As long as I’m alive, all the golfers will be white and all the caddies will be Black.”

Over the years, Bennett would caddie for Jones’ son at Augusta National and for pros ranging from World Golf Hall of Famers Raymond Floyd and JoAnne Carner, to Andy North, to Webb Simpson. Bennett never carried the bag for a victory on the PGA Tour but came close a number of times: He caddied for Jodie Mudd when Mudd finished 1 stroke out of a three-man playoff at the 1987 Masters. He caddied for Tom Pernice when Pernice lost to Phil Mickelson by a shot at Pebble Beach in 1998. He caddied for Matt Kuchar when Kuchar lost by 2 shots to Justin Leonard at the 2001 Texas Open.

Bennett estimates that in seven different decades, he has carried bags for thousands of rounds in country club tournaments, various mini-tour and senior events, PGA Tour and LPGA Tour events, and three of the four majors. (He has never worked the Open Championship.) And yet everyone always asks about the one player, the one week and the one chance he had to watch a young Picasso paint on Augusta’s emerald green canvas for the very first time.

In April 1995, 19-year-old Tiger Woods, weighing in at 6-foot-1 and 150 pounds, all arms and legs under his Stanford cap, could already clear the practice-range netting at Augusta that stood 50 feet high and 260 yards from the tee. With Tommy Bennett at his side, Woods arrived for his Monday practice round to great fanfare; he would be playing with five-time major winner and betting favorite Nick Faldo and British Amateur champ Lee James. Augusta National’s only two Black members, Ron Townsend and Bill Simms, walked with the group; Tiger was the fourth Black man and first Black amateur to play in the Masters. The oversized galleries couldn’t get close enough for their first look at the phenom, who gave them something to talk about on the 500-yard 15th hole when he blew his drive 70 yards past Faldo’s, hit a 9-iron to 4 feet and made the putt for eagle. “Faldo looked stunned,” Bennett recalls.

Woods grabbed lunch, then turned his first day at Augusta National into a 36-hole day. He had beaten Trip Kuehne in the most dramatic U.S. Amateur comeback ever, erasing a six-hole deficit in the final, and now the runner-up wanted another crack at him. They agreed to play a $5 match. Bennett was reading Tiger’s putts, picking his clubs and telling him where to land his approaches. “Damn, you’re good,” Woods told him late in the match, when Tiger, down three, charged past Kuehne again by winning the final four holes.

Bennett thought Woods was pretty damn good too. He noticed one unmistakable thing about Tiger’s ball in midflight: “It didn’t want to come down,” he says.

Woods played Tuesday with Greg Norman, Fred Couples and Floyd, who were more talkative and helpful than Faldo had been the day before. Norman came away thinking Woods could become the youngest man to win the Masters. By the time Tiger held his first news conference that day, he’d already annoyed some media members who had waited to talk to him Monday under the grand old oak tree behind the clubhouse only for Tiger to withhold comment. He didn’t help himself with the credentialed crowd in the formal presser either, when he called the Masters “just another tournament” and described himself as underwhelmed by the mystique of the place, including Magnolia Lane. (“I thought it was a very short drive,” he said.) More than two decades later, Woods would write in his book, “Unprecedented: The Masters and Me,” that he was underwhelmed in part “because the club had excluded black golfers from playing for so long.”

Tiger played Wednesday morning with Norman and Nick Price but cut his round short when he felt a spasm in his back on the fifth hole. He got treatment on site, then played the Par 3 Contest with Gary Player before his father made it official and informed Bennett that he had passed the audition. After Woods caught five hours of sleep and went on a Thursday morning run, he met Bennett at the course for his 1:03 p.m. opening-round tee time with defending champ Jose Maria Olazabal. The caddie looked inside Tiger’s black leather bag and found a problem.

“You’ve only got three balls,” Bennett told his player.

“That’s all I need,” Woods responded.

“Man, this is Augusta National,” Tommy told himself.

It was a raw, rainy day, and Woods’ heart was racing on the first tee. He crushed his opening drive over the right bunker and then landed his sand-wedge shot safely on the green, 25 feet from the cup. Woods had prepared for Augusta’s lightning-fast greens by putting on Stanford’s hardwood volleyball court, yet when he hit his downhill putt too hard, he watched in horror as his ball spilled off the green and toward the gallery. Bennett had never seen that before at the Masters. He told Tiger, “Listen, we all get nervous. We’ve got a long week here. Just chip it back up there and make the putt.”

Woods did as he was told from his messy lie, accepted his bogey, then pounded his driver on the par-5 second on his way to a two-putt birdie and, ultimately, an even-par round of 72 — 4 strokes better than Nicklaus shot as a 19-year-old in his first Masters round in 1959. “I needed binoculars to see where he hit the ball,” Olazabal said of Tiger. Woods would call the sight of his name on the leaderboard “the coolest thing ever.” He’d played one ball on the front nine and another on the back nine before playfully reminding his caddie that he still had one untouched ball left over. “The kid was so mentally strong,” Bennett says. “He was just in another zone.”

Tiger shot another 72 in the second round to make his first professional cut in eight attempts; the other four amateurs in the field missed the cut at a combined 52 over par. Woods then headed to a local public course, Forest Hills, to conduct a clinic for about 100 local youths and to spend time with Bennett’s fellow Black caddies, many of whom had been displaced in the 1980s, when Masters competitors were first allowed to use their own caddies instead of those employed by the club. Tiger said at the time that he wanted to honor the Black men who had helped make the tournament special.

He also wanted to put on a show. There at Forest Hills, Woods had his father stand about 30 yards in front of him while he fired 2-iron line drives in his direction, hooking and slicing them around and over Earl’s head. “I was like, ‘What the hell is going on here?'” Bennett recalls. “When they dropped me off, I said, ‘Man, somebody get me a damn drink.'”

But first, before Tiger and parents Earl and Kultida dropped off Bennett, Earl decided the family should see Tommy’s old neighborhood. They parked outside the Sand Hill Grill, where there was a mural of Bennett in his white Masters jumpsuit, caddying for Mudd, on the front brick wall, while Tommy told them about his upbringing. Bennett appreciated Tiger’s interest in his background; he found the college kid to be pleasant and respectful. On the course, Woods posed with Bennett as he held his 5-year-old son, Donte, in a picture that would later appear in Sports Illustrated.

Saturday, Round 3, changed things for Tiger and everyone around him. Bennett arrived at the club to find that extra Pinkerton guards were preparing to walk with his group and that Earl wanted Tommy to keep the conversation with his son to a bare minimum. Bennett asked the Pinkertons to explain the added security, and they declined to answer. But Woods had received threats and racist mail in the past, and he would again shortly after this Masters. Whatever happened, it didn’t help. Tiger’s iron game failed him and he shot 5-over 77. He called himself “distracted” and said he was “about ready to break something.” Tiger had won three consecutive U.S. Junior titles and had become the youngest winner of the U.S. Amateur. He expected to win the Masters too, but as he faced a 15-stroke deficit with 18 holes to play, he knew he had blown his chance.

Sunday brought better vibes. Earl gave Bennett the green light to resume caddying and counseling for Tiger, who was one of only six Masters players that week using club caddies. (That group included Ben Crenshaw, who would win for a second time with Sand Hills veteran Carl Jackson on his bag.) Woods birdied three of his final four holes and punctuated his 12-footer on the 18th with a fist pump before signing for his third 72. He finished in a tie for 41st and easily led the field in driving distance with an average of 311.1 yards. In a letter he wrote to Augusta National, Woods would call the experience “fantasyland and Disney World wrapped into one” and declare the Masters the place where “I left my youth behind and became a man.” The letter sounded nothing like his answers in his pre-tournament news conference.

Tiger had to leave the course quickly to catch a flight to Atlanta, and then another flight to San Francisco, to get back to Stanford in time for his Monday morning history class. Before he left, Bennett says, Tiger thanked him for his work and his wisdom.

“I don’t know if I’ll ever caddie for you again or not,” Bennett told him, “but you sure have a great future ahead of you.”

Tommy Bennett is enjoying a Yuengling after a round at the Patch a month before the coronavirus pandemic would shut down the country. His putter has been betraying him of late, dropping him to a 6 handicap, but that’s OK. He says he enjoys the camaraderie with old friends from Sand Hills and Augusta National, like Jariah (Jerry) Beard, who shepherded Fuzzy Zoeller to victory in Zoeller’s first Masters appearance in 1979.

They gather at the Patch, a place where the grass isn’t quite Augusta National green and the sand isn’t quite Augusta National white, to talk about the old caddie nicknames at the Masters, from Bennett’s Burnt Biscuits to Cemetery and Iron Man and Stovepipe. They talk about the huge purses in modern-day golf and how they inspired more and more college grads and struggling mini-tour players to get into caddying, a trend that helped drive Black caddies out of the Masters and off the PGA Tour. Of course, they talk about the player most responsible for the big-money explosion in the sport, Tiger Woods, and how last year he authored one of the greatest golf stories ever told.

Back in 1995, while carrying Tiger’s bag, Bennett gave the Masters rookie a piece of advice on how to play the pivotal 12th hole. Drawing on the strategy that Jack Nicklaus had forever used on the hole, Bennett told Woods to never go for the flag when it was on the left (you could end up in the bushes) or when it was on the right (you could end up in the water). “Hit it in the middle of the green, two-putt and then get the hell out of there,” Tommy told Tiger.

When a series of contenders drowned their chances in the creek at 12 last year, while Woods seized control of the tournament by playing it safely, Bennett was watching from the Patch with a smile on his face.

Tommy is a proud father of four sons and three daughters, including Donte, himself a caddie at Sage Valley, who has up on his wall that old picture of him in his old man’s arms next to a smiling Woods in his Stanford cap. Tonia, a daughter in the music industry, says the week her dad caddied for Tiger “is an amazing moment in our lives we’ll never forget.” Trevel Price, a son in the Bronx who is a bank project manager, business analyst and life skills coach who flies planes up and down the Hudson River corridor, says his father’s work on the golf circuit with Woods and others “has been tremendously inspiring to me, because he was able to find a way.”

Bennett found a way, through golf, just like many young men out of Sand Hills. “Augusta National was the love of my life,” he says. “That’s all we had. That’s all we knew. It’s how we made our living.”

Bennett hasn’t been back to the National in the more than two decades since he was let go, but he maintains that he harbors no ill will toward the club. He says now that he is just happy to be healthy in the middle of a pandemic. He savors the memories captured by the remains of the mural outside the now-shuttered Sand Hill Grill, and he fondly recalls the National’s annual end-of-season caddies day, when the loopers are allowed to play the course from sunup until sundown. “You might go 60 to 65 holes with a cart,” Bennett says. “When you got home, you were so tired you couldn’t even put your key in the keyhole.”

Yes, he has run into Woods a few times over the years and exchanged pleasantries with him, and no, he’s never found out why he wasn’t asked to work for him again. Bennett says he subscribes to an ego-free approach to golf and life. He was blessed to play an early role with a generation-defining athlete, and like legions of golf fans, he will sit back this week and hope Woods shocks the world again as he closes on his 45th birthday.

“I showed Tiger Woods how to play that golf course,” Tommy Bennett says, “and then he won five Masters with other people carrying for him. I made pennies while others made millions. And I’ll always be fine with that.”

ESPN’s Lauren Stowell contributed to this story.

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