Rick Reilly is a sportswriter with work in Sports Illustrated and ESPN. He is also a screenwriter and the author, most recently, of Commander-in-Cheat: How Golf Explains Trump, from which this is excerpted.
President Donald Trump’s two most loyal employees aren’t politicians or fixers or publicity flacks. They’re caddies.
He has a regular outdoor caddy—a 60-something ex-Marine named A.J.—who loops for him faithfully at Trump National Golf Club Washington, in northern Virginia.
And then he has a kind of indoor caddy—Dan Scavino, Trump’s social media director, and one of the very few staffers who’s remained in Trump’s orbit from the start of the campaign—who actually met Trump caddying for him when he was a teenager.
In a way, A.J. and Scavino are the same guy. They’re both mostly unknown, yet they know all the president’s secrets. Both do the same job, and it’s a fairly simple one: They give their man the right club to take shots with. These two work for a human flamethrower and yet somehow haven’t been torched. Cabinet members, attorneys general, chiefs of staff come and go like the Wendy’s drive-thru and yet they stay employed.
What do A.J. and Scavino know about keeping the most powerful man in the world happy that others don’t?
Take A.J. first.
A.J. (who asked that I not use his last name in my book) is so loyal that if someone criticizes Trump, he’ll fight him—and has. One day, when the 2017 Senior PGA Championship was being held at Trump Washington, he overhead one of the Tour pro’s caddies—Brian “Sully” Sullivan—dissing Trump.
“He was running his mouth, sir,” says A.J., who calls everybody “sir” or “ma’am.” “Yellin’ about Mr. Trump. He was sayin’ to somebody, ‘Don’t tell me how I have to feel about him! I hate that motherf—–!’”
A.J. says he came up on Sully from behind and put him in a full military choke hold, yelling, “Now, you listen to me, f—–! You’re not gonna come to Mr. Trump’s course and eat Mr. Trump’s food and then use the word ‘hate’ about my president. I won’t have it, you got me?”
That’s not quite the way the story is told by Sullivan, who caddies for Senior Tour player Joe Durant, but his memory is a little fuzzy. “It’s possible I was hungover,” Sullivan recalls. “I don’t like D.C. anyway and I sure as hell didn’t want to be on a Trump course. Some guys started talking about Trump. I mentioned that I can’t stand the son of a b—-. I said he was the biggest jerk in the world. A.J. got all worked up and said, ‘That man pays my rent. He puts food on my table!’ I said if he has to take money from that horse’s ass, then he ought to find a different loop. He kind of just grumbled off. Of course, as luck would have it, he and I got paired for the first two days. We buried the hatchet.”
Tensions were high because, for seniors, it was a big tournament and Trump’s name was attached to it. There were protesters by the entrance every day that week, and A.J. always made sure to drive his car right by them. “There’d be a bunch a women out front with all their stupid signs, sir. So I go real slow by ’em, see, hit the window button—zzzzzzttt—toss ’em the bird and I yell, ‘F— you!’ They’d start yelling at me and I’m like—zzzztttt—right back up. And I laughed, sir.”
A.J. sticks with Trump no matter how much it costs him. “I used to caddy for a lot of the ladies here, sir,” he says, meaning the female members of the club. “But once Mr. Trump won the election, that all ended. Now I hardly do it at all, sir. I guess they don’t like him. I’m the president’s caddy and they’re not gonna ask for me, sir. So that’s it.”
One time, after a bad drive, Trump slammed his driver back in his bag, as guys will do, and wasn’t really watching what he was doing, and the driver ricocheted back and hit Trump in the head. “A.J.?” Trump asked, pissed. “Did you just hit me in the head with my own driver?”
“Sir, Mr. Trump, why would I do that?” A.J. said. “You’re my president!”
There are more than a few members at Trump Washington who’d love to hit Trump in the head. A valet told me, “We had a bunch of them quit when he won.” Most of the anti-Trump crowd stayed, but they resist in their own small ways.
Every time one member sees A.J., he says, “Is this the day, A.J.? Is this the day?”
“Is this the day for what, sir?”
“Is this the day you take him out for me?”
“This one time, we’re playing through, sir, like we do and, you know, usually the Secret Service has the people standing on the side in plenty of time for us. But this one guy, sir, young guy by the name of Jonathan Wallace, he was taking his sweet time getting out of the way. He was just moseying along, sir, doing it on purpose. Then he gives it one of these”—A.J. flips the bird— “right to Mr. Trump. Sir, that really made me mad.
Mr. Trump just asked me who it was. I told him. He said, ‘Let’s go say hello.’ Not me, sir. I went the other way. But Mr. Trump went over there and talked to him. Right away, this Wallace guy caved, sir. He caved.” (I couldn’t get Jonathan Wallace to call me back to hear his side of it
None of this used to be A.J.’s life. His Trump days used to be filled with pro athletes or businessmen. Now it’s congressmen and Fox hosts. Among his favorite these days is South Carolina Sen. Lindsey Graham, a Republican. “I love hearing that accent of his, sir. Mr. Trump plays pretty good with him. One time, he taught Mr. Trump a game called ‘Hogan.” This was in 2017. “A Hogan is when you hit the fairway and the green and then two-putt. You do that, you get one Hogan point. So we played it, and, bam, Mr. Trump gets a Hogan on the first hole. And he just keeps going. Mr. Trump got 11 Hogans, sir! Shot 73 that day, I kid you not, sir. He made about four 15‑ to 20‑foot putts on the back and shot 73. Coulda been even lower.”
A one-over par 73 on a “wet and windy day” as Graham described it, for a 72‑year-old overweight man? That’s unbelievable. How unbelievable? Well, at that same Senior PGA Championship, at the same course, from the same blue tees, professional golfer Tom Watson never shot better than 74. Tom Kite put up a 75 and an 80. Corey Pavin had an 82. Between them, those three men have won nine majors.
When asked by a reporter how many gimmes there were in that 73, Graham allowed that they didn’t really putt out that often and that “the president is better at receiving than giving.” So, in other words, that 73 had more sugar in it than a family pack of Butterfingers. Now why would Graham tell the truth about Trump’s scorekeeping skills? Perhaps because of the vitriol Trump tweeted about him during the 2016 campaign, calling him “nasty” and “so easy to beat” and a man with “no honor.”
Now, though, Graham is No. 1 on Trump’s golf speed dial.
Graham remembers legendary Republican Sen. John McCain asking him why he kept playing golf with someone like Trump. “I told him, ‘I hope you understand … The best place to talk to him is in his world.’”
A.J. had Trump and Tennessee Republican Sen. Bob Corker in his world one day—along with no less than former NFL quarterback Peyton Manning—but it didn’t seem to grease any wheels for his boss in Congress. Not long afterward, Corker said Trump needed “adult daycare.”
A.J. has no time for another Republican senator, Kentucky’s Rand Paul, whom he calls “a real chooch.”
“Yeah, I don’t know how to translate it, sir. A chooch. He treated me like a peon. Never even tried to fix a ballmark. Treated me like dirt, sir. He’s a rich guy who thinks he’s above everybody. A real chooch, sir.” (Paul didn’t return calls.)
Paul didn’t sound like he had that much fun playing with Trump and A.J., either. When asked who won the golf match, Paul told reporters after the game, “The president never loses, didn’t you know?”
In my 18 holes with A.J., he didn’t say a single negative thing about Trump. He didn’t even say a neutral thing about Trump.
To hear A.J. tell it, Trump has Einstein’s brain, Lincoln’s wit and Nightingale’s heart. A.J. is smart that way. A loyal caddy can go a long, long way with Donald Trump.
Take Dan Scavino.
Scavino was a 16‑year-old summer caddy when he got Trump’s bag one day in 1990 at Briar Hall Golf and Country Club in New York, which was to become Trump Westchester. “I’ll never forget the day his limo first pulled up,” Scavino told Westchester Magazine in 2012. “I was star-struck. I remember his first gratuity. It was two bills—two hundred-dollar bills. I said, ‘I am never spending this money.’ I still have both bills.”
The two hit it off. Trump told him, “You’re gonna work for me one day.” Scavino graduated from State University of New York, Plattsburgh, in 1998 and went to work for Coca-Cola, but Trump brought him back soon enough to be the assistant general manager at Westchester. Then Scavino became executive vice president. When Trump decided to run for president, Scavino asked if he could be part of the campaign. Trump made him social media director.
A billionaire and a caddy is a friendship that could only be made in golf, where kings can take orders from cobblers and lifetime allegiances are sealed over 6-irons. It was the perfect match. Scavino is Trump’s Mini Me. They both speak fluent golf. Both love stirring up liberals. Both are often very short on details and understanding, but long on Atomic Pile Driver slams and face-first personal takedowns.
“They share thumbs,” former campaign advisor Barry Bennett says. “They complete each other’s tweets.” Neither is well read nor a particularly good speller. Doesn’t matter. As a two-man Twitter team, they shout from the rooftops anyway. They find a phrase—“fake news” or “enemy of the people” or “Crooked Hillary”—and repeat it so many times, people start to accept it.
When Scavino took over Trump’s feed in 2016, Trump’s tweets became even more bombastic, ultra-opinionated, and, often, a par 5 over the line. They became longer, and more punctuated with exclamation points. Former White House communications czar Hope Hicks called Scavino “the conductor of the Trump Train.” One day, in early July 2016, the train jumped the tracks. Trump tweeted out an image of Hillary Clinton, with a Star of David, against a background of money and the line “Most corrupt candidate ever!” It was a Scavino special, cobbled together with cut-and-paste images from the internet and no thought of maybe asking somebody, “Hey, is this too much?”
Within seconds, Trump was blasted as anti-Semitic. Scavino had to issue a statement taking responsibility. He tweeted:
The social media graphic used this weekend was not created by the campaign. It was lifted from an Anti-Hillary Twitter user. The sheriff’s badge, which is available under Microsoft shapes, fit the theme of corrupt Hillary and that is why I selected it.
Except it wasn’t a sheriff’s badge; it was a Jewish star. (It was probably a mistake on Scavino’s part, since his wife is Jewish.)
The more Scavino pumped up Trump’s tweets, the more it sounded like the Twitter feed of somebody else—Scavino’s. For instance, on March 2, 2016, Scavino tweeted on his own account:
@MittRomney, You will not stop the #TrumpTrain You look like a complete LOSER. Very DESPERATE attempt. #Fail
Hmmm. That’s got a certain ring to it. Another time, just days before the election, Scavino tweeted, again on his own account:
NBC news is #FakeNews and more dishonest than even CNN. They are a disgrace to good reporting. No wonder their news ratings are way down!
A minute later, the same message, word for word, was posted on Trump’s account as his original tweet. Scavino hastily deleted his, but in a world of screenshots, it was too late.
Robert Draper, of the New York Times Magazine, conducted an exhaustive study of Trump’s tweets and estimated that Scavino was “responsible for—at least as a ‘co‑conspirator’”—about half of Trump’s 37,000 tweets. The late-night and early-morning tweets seem to be 100 percent Trump, but the daytime stuff has the patina of Scavino.
Whichever it is, neither of them particularly knows what they’re doing. Scavino may have violated the Hatch Act by tweeting support for a candidate. Trump and Scavino got dragged to federal district court for blocking some followers, which, some argue, is unconstitutional for an American president.
Still, he’s put Trump’s Twitter rants on a kind of steroid regimen. Fox News host Megyn Kelly accused Scavino of rabble-rousing against her: “The vast majority of Donald Trump supporters are not at all this way,” Kelly told an audience in Washington in late 2016. “It’s that far corner of the internet that really enjoys nastiness and threats and unfortunately there is a man who works for Donald Trump whose job it is to stir these people up and that man needs to stop doing that. His name is Dan Scavino.”
But just think of it: Trump’s Twitter feed is the most powerful pulpit on the globe, and Trump’s former golf caddy has his hands on it, daily. It’s full-throated Trumpness, even Trumpier than Trump, sent without censure or concern and teeming with what former President George H.W. Bush called Trump’s “casual cruelty.” It’s a flamethrower that sometimes winds up setting the Oval Office curtains on fire. During his 2012 campaign, Mitt Romney had 22 people approve each tweet before it went out. During the day, Trump has two—himself and his caddy. At night, just one. That’s not going to change.
In 2016, CNN asked Scavino if there was anything Trump could do or say that would make him leave Trump’s side. He answered with an unequivocal “no.”
Scavino refused my requests to interview him, but we know he’s a Catholic who once kissed Pope John Paul II’s ring. He was about 40 when Trump was elected. Scavino’s wife, Jennifer, became sick with Lyme disease, and the couple says they spent so much money trying to get her well, they went bankrupt in 2015. Some people say this is why they got divorced after 18 years. “Dan was a great husband, though,” says Ian Gillule, who worked with him at Westchester. “He’s very gregarious, a big personality, a people pleaser and very political.” Also, apparently, not a guy who will ask his billionaire boss for a loan.
What’s A.J. and Scavino’s secret? It might be the Caddy Code: Show Up, Keep Up, Shut Up. It only takes one bad read or one bad club to get fired as a caddy, but A.J. has been Trump’s loop for years now. Scavino has survived Trump’s well-oiled guillotine and remains one of the few staffers who’s lasted since the beginning.
A president who trusts nobody trusts Scavino. “The president has zero concern that Dan has any interest in anything but serving him,” the New York Times quoted a top administrator as saying. When you’re the only other person who has the president’s Twitter password, you’re trusted.
All of which proves one thing. Former Attorney General Jeff Sessions should have learned to caddy.