Commander in cheat: what is it like to play golf with Donald Trump?

In golf, as in life, President Trump is a winner — and he won’t let little things such as etiquette, or the rules, get in the way. Rick Reilly talks to caddies, teammates and opponents about how he fudges his way to glory

The Sunday Times, 

In the three decades that I’ve known Donald Trump, I’ve never believed anything he said, but the wink-wink of it was that I never thought he believed any of it either. One time, for instance, I was in his office in Trump Tower. He pulled a yellow laminated card out of his wallet and slapped it down on his massive desk like a fourth ace. “Look at that,” he said. “Only nine people in the world have that.” The card read: Bearer Eats Free at Any McDonald’s Worldwide. “It’s only me, Mother Teresa and Michael Jordan!” he crowed.

I pictured Mother Teresa pulling into the drive-thru at the Calcutta McDonald’s, rolling down the window, leaning her habit out, and saying, “I need 10,000 double cheeseburgers, please.”

I liked Trump the way I liked Batman. He was what eight-year-old me thought a gazillionaire should be like — his name in 10ft-high letters on skyscrapers and on giant jets, hot and cold running blondes hanging on each arm, $1,000 bills sticking out of his socks.

The first time I met him I was a columnist at Sports Illustrated. I was playing in the AT&T Pebble Beach Pro-Am golf tournament when he came at me with a Bible-salesman grin and a short-fingered hand to shake. His wife, Marla Maples, was smiling at me, too. Uh-oh, I thought. What’s this? “You’re my favourite writer!” Trump bellowed. “I love your stuff. Tell him, Marla.” “He does,” she said. “Look!” And she pulled out of her purse a column I’d written. OK, there was the set-up. What was the hook? “So,” he said, “when are you going to write about me?” Ah, there it was.

No problem. Trump was the most accessible, bombastic and quotable businessman in the world. Why would I turn that down? So when I set out to write my 2003 book Who’s Your Caddy?, in which I would caddy for 12 golf legends, celebrities and oddballs, I asked if he wanted to be a chapter. “Absolutely!” he said.

When the day came, he didn’t have anybody to play with, so he announced that I wouldn’t be caddying for him, I’d be playing with him. OK, you take what you can get. We played his Trump National Golf Club Westchester in Briarcliff Manor, New York, and it was like spending the day in a hyperbole hurricane. Trump didn’t just lie nonstop about himself that day. He lied nonstop about me. He’d go up to some member and say: “This is Rick. He’s the president of Sports Illustrated.”

The guy would reach out to shake my hesitant hand, but by then Trump had dragged me forward to the next member. Or secretary. Or chef. “This is Rick. He publishes Sports Illustrated.” Before I could object, he’d go: “And this is Chef. He was voted best hamburger chef in the world!” And the poor chef would look at me and shake his head with a helpless “no”, same as me. When we were alone, I finally said: “Donald, why are you lying about me?”

“Sounds better,” he said. Sounding better is Trump’s modus operandi. It colours everything he says and does. The truth doesn’t break an egg with Trump. It’s all about how it sounds, how it looks, and the fact-checkers can go run a 100yd dash in a 50yd gym.

Trump lies, and Trump cheats. When he and I played that day at Westchester, he took “floating mulligans” — second chances on shots whenever it suited him — and simply subtracted shots when it came time for me to write his score down. “I have to take a newspaper four once in a while,” he said. A “newspaper four” is when you write down a four on a hole on your scorecard when you really made a five or worse. It looks better in the newspaper the next day.

I also heard I’m-taking-a-mulligan excuses like: “You distracted me.” “That bird flew over just as I was about to hit.” “My foot slipped.”

The man even took a “gimme” chip-in that day. A gimme is usually a putt that your opponent concedes you will make. He says, “That’s good,” meaning, “I concede that you’ll make that putt, so just pick it up.” Gimmes are illegal in stroke play under the rules of golf, but as common on the course as hot dogs. Still, a gimme should not be longer than 2ft, 3ft tops. Gimmes are supposed to be like gifts: they can only be given, never taken. Except for Trump. He’ll declare any putt he has under 5ft, or 6ft, or 8ft a gimme and scoop it up.

The Donald Trump golf quiz
Do you know what Trump’s ‘invisible dunk’ is and the handicap he claims to have? Test your knowledge

Take the quiz

And as you go to pick your shorter putt up, too, he stops you and warns that “You better brush that in”. He’s the conductor of the Trump Train and you’re just hanging on to the caboose.

But never in the history of golf has anyone taken a gimme chip-in until Trump did that day with me. I was in the hole for a five and he was lying off the green in five, and he said, casually, “Well, I guess that makes this good,” and scooped the ball up.

I was gobsmacked. We were playing a $10 medal bet — ie, a total-score bet — so every shot counted. Even if he could’ve chipped it close — which he wouldn’t have — he’d have made a seven.

“Did you just take a gimme chip-in?” I asked, dumbfounded.

“Well, yeah, ’cause you were already in for five.”

By the time I got my jaw refastened, he was driving off in the cart. I put the scene in my book. When he was running for president, The Washington Post asked him about that gimme chip-in. Trump had a very odd answer: “I don’t do gimme chip shots. If I asked his approval, that’s not cheating, number one. Number two, I never took one.”

So that clears that up.

In the end, the scorecard said he beat me. The rules had been pulverised into pea purée by then, so I paid up the $10. Then he bought lunch. It’s not the money; it’s the winning.

No American president has been as up to his clavicles in golf as Donald Trump. None has been woven so deeply into the world of golf. Trump doesn’t just play courses; he builds them, buys them, owns them, operates them, sues over them, lies about them, bullies with them and brags about them. From the people he knows, to the businesses he runs, to the favours he hands out, to the access he grants, to the trouble he gets into, to the places he goes, to the money he makes, to the money he loses, to the opinions it informs in his brain, Trump’s soul is practically dimpled. But keep on your toes, ballerinas, because it’s a wild dance.


Trump doesn’t just cheat at golf. He cheats like a three-card monte dealer. He throws it, boots it and moves it. He lies about his lies. He fudges and foozles and fluffs. At Winged Foot, where Trump is a member, the caddies got so used to seeing him kick his ball back onto the fairway, they came up with a nickname for him: “Pele”.

“I played with him once,” says Bryan Marsal, longtime Winged Foot Golf Club member and chairman of the coming 2020 US Open. “It was a Saturday morning game. We go to the first tee and he couldn’t have been nicer. But then he said, ‘You see those two guys? They cheat. See me? I cheat. And I expect you to cheat because we’re going to beat those two guys today.’ So, yes, he’s going to cheat you. But I think Donald, in his heart of hearts, believes that you’re gonna cheat him, too. So if it’s the same, if everybody’s cheating, he doesn’t see it as really cheating.” OK, but . . .

a) Everybody isn’t cheating. Except for an occasional mulligan on the first tee and accepting a gimme from an opponent, 85% of casual golfers play by the rules, according to America’s National Golf Foundation.

b) To say “Donald Trump cheats” is like saying “Michael Phelps swims”. He cheats at the highest level. He cheats when people are watching, and he cheats when they aren’t. He cheats whether you like it or not. He cheats because that’s how he plays golf, that’s how he learnt it, that’s how he needs it, and whether you’re his pharmacist or Tiger Woods, if you’re playing golf with him, he’s going to cheat.

In fact, he did cheat with Tiger Woods. Not long after becoming president, he invited Woods, Dustin Johnson (the No 1 player in the world at the time) and the longtime Tour pro and Fox golf analyst Brad Faxon to play. They set up a bet: Faxon and Trump against Woods and Johnson. But because Woods and Johnson are so preposterously long off the tee, they decided Faxon and Trump could tee off the middle tees. Trump would get a stroke subtracted on the eight hardest holes; everybody else would play scratch. Off they went. “On this one hole, Donald hits his second and fats it into the water,” Faxon remembers. “But he quickly says to me, ‘Hey, throw me another ball; they weren’t looking.’ So I do. But he fats that one into the water, too. So he drives up and drops where he should’ve dropped the first time and hits it on the green.”

Meanwhile, on the other side of the fairway, Woods, being Woods, has hit his approach to 1ft from the hole for a kick-in birdie. Everybody’s on the green now, with Trump about 20ft from the hole and getting a stroke. Trump said, “So, where does everybody stand here?”

Faxon: “Well, Tiger just made a three. What’s that [putt] for, Mr President?”

Trump: “Four for a three.”

Faxon had to laugh because Trump was actually putting for a seven, but was claiming it was for a four, which would’ve worked out to a three with his free stroke on the hole. “How great is that?” Faxon recalled. “Four for a three! But he missed it anyway. It was really fun to play with him. He rakes [picks up] every putt [as if it’s conceded], but you kind of want him to. You’ve heard so much about it, it’s almost like you want to witness it so you can tell the stories.”

Trump consistently says he doesn’t cheat. “I never touch the ball,” he says. That’s sort of true, maintains the actor Anthony Anderson. “I’m not going to say Trump cheats. But if Trump’s caddy cheats for him, is that cheating?”

“We clearly saw him hook a ball into a lake at Trump National [Bedminster, New Jersey],” the actor Samuel L Jackson once recalled, “and his caddy told him he found it!”

So what do the caddies say?

“Whenever I’ve caddied in Trump’s group,” says the player, caddy and 2000 US Mid-Amateur champion Greg Puga, “he always gets his own cart. He makes sure to hit first off every tee box and then jumps in the cart, so he’s halfway down the fairway before the other three are done driving. That way, he can get up there quick and mess with his ball. So this one time — we were on the 18th — he hits first, kind of blocks it right, and jumps in his cart and starts driving away. My guy pures one right down the middle. I mean, I saw it go right down the middle. One of his best drives of the day. But by the time we get to my guy’s ball, it’s not there. We can’t find it anywhere. And Trump is now on the green already putting! Where’s our ball? And then Trump starts yelling back at us, ‘Hey guys, I made a birdie!’ He’s holding up his ball and celebrating. And that’s when we realised. That f***** stole our ball! He got up here early, hit our ball, and then hurried up and pretended like he made the putt for a birdie. I mean, what the hell?”

Once, Trump played a course with one of LA’s more famous holes — a par five where Howard Hughes once landed his plane to pick up Katharine Hepburn for a date — that has a pond just left of the green. “I saw Trump’s ball go in the lake,” one of the caddies told me. “I mean, I saw the ripples! But by the time we caught up to him and his cart, the ball was back on the fairway. When we asked him what happened, he said, ‘Must’ve been the tide.’ ”

A group of caddies I spoke to at Bedminster all agreed Trump was a good player, with a handicap of “eight or nine”, they all said, knowing full well that he tells the world he’s a three. Does he cheat? There was a lot of sudden interest in birds outside the window. One caddy held his hand up while looking me right in the eye. His expression was flat, but his eyes were wide, like he was about to give me a clue.

“Donald Trump never cheats,” he said, slowly and sternly. He stared at me. Blink. Stare. Blink.

“Oh!” I said. “His caddy cheats for him?”

The entire room howled. What followed was a dozen or so stories about just how he cheats.

“He’s always got four balls in his pocket, if that tells you anything.”

“He foozles [botches] his ball on every hole. All 18. I promise you. Every hole.”

“He wants you to throw it out of the woods, kick it out of the rough, fluff up his lie. We all know the deal.” Most of them said they didn’t mind doing it, but felt a little bad when there was money on the line or a tournament going on.

“I have a friend at his course in Palm Beach,” one caddy said, “a really, really good player. He’s a plus-three or plus-four [ie, he averages three or four strokes over par]. It kills him to do what you gotta do when you caddy for Trump. It absolutely kills him.”

All the cheating Trump’s caddies do for him actually hurts his game. His only real weakness, besides the ethics bypass he seems to have undergone, is chipping around the greens, where he’s just awful. That’s why his caddies fluff up nasty lies, take his balls out of bunkers and kick his ball onto the green out of the cabbage. But if you never have those lies, you never learn how to hit them. “Because of the caddies, he never gets to practise those hard shots around the green,” says Ned Scherer, who has played with Trump at least 10 times and is a member of both the Trump DC and Trump Jupiter golf clubs. “Golf is all about practice, but he never even gets to try them.”

People like to tell about the time Trump hit one in the pond at Bedminster. Everybody saw it splash a good 30ft from shore. When the group got up to the pond, Trump’s caddy says: “Boss, your ball is right here.” It was sitting safely on grass. Somebody yelled at the caddy: “What did you do with your mask and flippers?”


Like so much of what happens with Trump, the caddies were revolted by the immorality of the cheating, but impressed by the genius of it. “For a while he kept a can of red spray paint in his cart,” one caddy said. “Whenever his ball hit a tree that he didn’t think was fair, he’d go up and paint a big X on it. The next day, it was gone.”

Trump’s cheating during a round is legendary, but his cheating after the round is just as sharp. His score always gets what I call the Trump Bump. He may wrap up a very sketchy 77 at noon. On the ride home, it’ll be 75. By dinner, 72.

It’s not just his score that gets the Trump Bump. It’s anybody’s score he likes. The major-winning golfer Lee Trevino tells about the time he played one of Trump’s courses, shot a 72, and then ran into Trump in the locker room. “What’d you fire?” Trump asks. “Seventy-two,” Trevino says. Trump is delighted and wants to start introducing the legend around his clubhouse. “This is the great Lee Trevino. He just shot a 70!” For the next person, it was: “You know who this is? Lee Trevino. He just shot a 68!” Then it was: “He just shot a 66!” Says Trevino: “I had to get out of there before I broke the course record.”

Trump cheats. Trump lies. But when I read The Big Lie, it nearly made me spit out my Cheerios. It was a tweet he’d originally posted in 2013, but I hadn’t read it until his presidential election campaign began. Trump was embroiled in one of his hundreds of celebrity feuds, this one with somebody in his weight class — the billionaire Mark Cuban. Cuban had dissed him on some forgettable TV show years before. “I think I said, ‘I can write a bigger check than Trump right now and not even know it was missing,’ ” Cuban recalls. Trump vowed revenge on Cuban that day. That’s when he challenged Cuban.

“Golf match? I’ve won 18 Club Championships including this weekend. @mcuban swings like a little girl with no power or talent. Mark’s a loser” — Donald J Trump, Twitter, March 19, 2013.

Eighteen club championships? That’s like an NFL quarterback telling you he’s won 18 Super Bowls. It’s preposterous. It is a lie that’s so over-the-top Crazytown, it loses all credibility among golfers the second it’s out of his mouth.

Besides, Trump had already given away his little secret of how he does it that day at Westchester. “Whenever I open a new golf course,” he told me, “I play the official opening round and then I just call that the first club championship. There you go, I’m the first club champion! That’s off the record, of course.”

You gotta admit: it’s sleazy, it’s morally bankrupt, but it’s pretty clever. I did keep it off the record, for years. But then he kept bludgeoning people over the head with it. “You know, I’ve won 18 club championships,” he said half a dozen times during campaign stops before the 2016 presidential election. “I’m a winner.”

Of 18 club championship “wins” that Trump listed for Golf Digest, 12 are actually senior or super senior club championships — at most clubs reserved for players aged 60 and older. They’re like bowling with bumpers.

“I remember Melania used to ask us, ‘What is this super seniors?’ ” recalls the former Trump Westchester exec Ian Gillule. “And Mr Trump would say, ‘Oh, super seniors is better than just a regular club championship, honey.’ He was saying it tongue in cheek, but she didn’t know the difference.”

So of the 18, that leaves six real club championships. One was at Trump Westchester 2001, when the club wasn’t officially open yet. That leaves five. The next was Westchester 2002, when the club was only nine holes. If it really happened, you can’t count that. That leaves four, one of them being Westchester in 2004. Could he have actually won that? “Well, no, I know for a fact that’s not true,” Gillule says. “He never won any in the eight years I worked there. I mean, I loved working for Mr Trump, but you know, some people take a certain licence with the truth.”

That leaves three possible club championship wins, all at one course — Trump International in West Palm Beach. We know the 1999 win there is a lie, since the course wasn’t open. That leaves two — 2001 and 2009 — and I have never seen a signed scorecard or spoken to any objective person who remembers him winning or not winning. Final score on the “18 club championships”: Lies 16, Incompletes 2, Confirms 0. By this time, Trump’s nose has grown so long he could putt with it.

The whole thing bugged me so much I started to itch. I wasn’t offended as a voter. I was offended as a golfer. You can’t get away with that. You want to make political promises you can’t keep? Great, knock yourself out. You want to invent tales of your cut-throat savvy in business deals? Live it up. But golf means something to me. I’ve played it my whole life. One of the things I love the most about it is that you’re your own referee. You call fouls on yourself. Integrity is built into the fabric of the game. Honesty is more precious in golf than the little white dimples. As Ben Crenshaw likes to say: “Golf is a game with a conscience.”

It got me thinking. When Trump held endless 18-hole meetings at his Florida courses with this prime minister and that emperor, were these leaders returning home to laugh at our president the way they laughed at him at the United Nations? Would they think all Americans cheat at golf? Somebody should point out that the way Trump does golf is sort of the way he does a presidency, which is to operate as though the rules are for other people. Somebody should explain that facts and truth are to Trump what golf scores and crowd sizes are — “feelings” — malleable and negotiable, flitting this way and that like an arm-waving inflatable car-lot balloon man. “Golf is like bicycle shorts,” I once wrote. “It reveals a lot about a man.”

© Rick Reilly, 2019. Extracted from Commander in Cheat: How Golf Explains Trump by Rick Reilly (Headline £14.99), published on April 2


Etiquette the Trump way

Just in the simplest politeness of the game, the timeless etiquette of it, Trump seems to have come from another planet. For instance, he never takes off his hat for the traditional end-of-round handshake, which is considered gentlemanly. He doesn’t take it off inside the clubhouse, either, which is a little golf-gauche. He doesn’t care whose honour it is on the tee. He just steps up first and hits it. He’s not what you’d call a good loser, either.

“I played with him once,” says the Los Angeles Times NFL writer Sam Farmer. “And I actually beat him out of $10. He handed me the two fives, but they wouldn’t quite come out of his hand. He held onto them and made me pull. I thought they were going to rip. When I finally got them, he goes, ‘It’s all right. I’ve got a supermodel girlfriend and my own 727, so I’m OK.’ ”

This is a man who famously drives his golf cart on greens. There is video of him doing it at Trump Bedminster. In golf, that’s the unholiest-of-unholies. Driving your cart on the green is like hanging your laundry in the Sistine Chapel. Caddies don’t even set their bags on it. Driving on the green leaves tyre tracks on the perfect surface that can send your partner’s putt careening off line, not to mention the putts of the 100 players behind you. I’ve met people who were 100% for Trump politically but vow they’ll never vote for him again because he drove on the green. Says one woman: “That’s such a violation!”

About Robert Stewart

Robert S. Stewart is a Canadian/Swiss entrepreneur, financier, investor, Master Planner, explorer, scientist, adventurer, athlete, Corporate Director, Chairman and CEO of numerous global enterprises including those in mining, petroleum, infrastructure, telecoms, aviation, hospitality and medical research . Currently, he has invested in the construction of the world's first integrated cacao plantation (103 hectares), chocolate processing factory in Costa Rica. Cacao beans are normally sold into the world market and processed into chocolate in the Northern Hemisphere, far from the planters and plantations of the Tropical zone where they grow. Modern, industrial chocolate has had the bitter mass from poor quality beans provided by 95% of Forestero beans removed from them and replaced by massive amounts of white beet sugar, soya and other additives. Criollo and Triniterio beans from Central America are the best beans in the world, where they first grew 4000 years ago. Adding value and paying the workers adequate salaries and prices for their high quality beans will lift them and Third World economies out of poverty. He created the World Ocean Corporation to clean-up plastics, toxic chemicals, municipal and industrial waste; replenish decimated fish stocks in the Mediterranean Sea, North Sea, Pacific, Atlantic, Indian and Arctic Oceans; and to build protection and exclusion zones for reproducing fish, mammal, animal and aviary species found in the oceans covering 71% of the Earth's surface. He writes frequently in the OP ED pages of the New York Times, Financial Times of London, The Economist, Toronto Globe and Mail,, The Times and Telegraph of London, Winnipeg Free Press and the Victoria Beach Herald. These are reprints of his editorial and OP ED pieces and comments on those who write better articles than his own. While he uses his own name or Email address to identify the writer of his articles, occasionally he is forced to use a "nom de plume" by the editors. "Beaverbrook" passes for that, after three generations of family dogs of the same name. It's a dog's world.
This entry was posted in Op-Ed's in Major Publications. Bookmark the permalink.