Golf Digest Logo TALES FROM HIGH UP!

The best (and craziest) stories of golfers flying private never told

Tour pros and amateurs share moments of mile-high high jinks
December 07, 2023
Illustration By: Jacquie Boyd

Golf and private aviation have grown up together. As early as the 1950s, West Virginia businessman and legendary amateur Bill Campbell piloted his Cessna “taildragger” to tournaments with Sam Snead as a regular passenger. When Arnold Palmer hung up his wings after a final flight from Palm Springs, Calif., to Orlando in 2011, at age 81, air-traffic controllers along the way radioed in to pay tribute. They also cleared the airspace, allowing tail number N1AP (November One Alpha Papa) to set a speed record.

Today most of the top-50 pros are regularly skipping the regular terminal. With oil barrels of money transforming the professional game, even caddies are hitching rides. Just be careful about posting photos of any mile-high high jinks on the ’gram, Four Aces Golf Club, because that might draw the ire of whoever’s footing the bill.

Unless you can afford to fly private until the day you die, you can’t afford to fly private. However, with the greatest new courses being built in ever more remote destinations, good luck dissuading any eager middle-handicapper with access to a PJ. In this moment of outsize executive compensation, meaningless commercial airline points and conspicuous consumption, it seems more people are realizing how perfectly the number of golfers on a buddies trip matches the capacity of a private aircraft. What follows are the stories from these lucky bastards. Must be nice. —MAX ADLER

POLICE ESCORT

The most luxurious accommodations I’ve ever experienced were on Herb Kohler’s jet—my wife had her own “bedroom” but was too excited to sleep on the overnight flight to Leuchars, Scotland. The biggest private jet I’ve ever been on, of course, was Donald Trump’s, long before he was president. It was a full-size 757 with gold-plated everything. I remember he showed me his bedroom, and it had an oil painting on one wall. He insisted I sit in the cockpit as the pilot landed at LaGuardia, where Trump said his was the only private jet ever allowed and promised that we would receive an NYPD escort off the runway, which, sure enough, we did. —JERRY TARDE

PIZZA ON THE TARMAC WITH COUPLES

We were flying back from the Canadian Skins Game: Quebec City to Phoenix. It was going to take more than nine hours, so a re-fueling stop was built into the itinerary. Fred Couples was on the plane, as was my best mate, Ben, from Australia. Ben was having the time of his life hanging out with Fred, who had always been one of Ben’s heroes. We were about to land in Tulsa, at which point someone said they were hungry. We quickly ordered pizza to be delivered to the airfield. The timing was perfect. Moments after we touched down, the two of us stood on the runway eating pizza off a wing of the plane with Fred Couples. It doesn’t get more random than that, but Ben thought those few minutes were the best time ever. —GEOFF OGILVY

FLYING WITH JACK

I flew a few times on Jack Nicklaus’ Gulfstream IV jet—I think the call letters were N1JN—but my most memorable flight with him was in the North Carolina mountains on a helicopter that nearly crash-landed. Clearly, there was some mechanical failure. We went up and up and then straight back down with all the aerodynamics of a shopping cart. When the skids hit the ground and bounced, Jack was the first one to jump. “Let’s get outta here,” he said. I always thought that would have been an ignominious end, the headline reading: “Golf Greatest Jack Nicklaus and One Other Killed in Chopper Crash.” Jack said that the difference between a plane and a helicopter is that the plane wants to fly. —JT

A CLOSE CALL

For a while, Arnold Palmer never tried any overseas trips on his Citation III because it didn’t have a great deal of range. Once he flew commercially to Asia on a business trip, but for the return he decided to have his friend and copilot Lee Lauderback fly the Citation III to Hawaii to meet him in Honolulu halfway. The computations looked fine flying from the West Coast to Hawaii, and it was fine going there. But on the way back to San Francisco they encountered strong headwinds and began to get concerned with the fuel supply. It got so serious that they rerouted to Monterey Airport near Pebble Beach, which was the nearest airport on dry land. Luckily, they landed without delay. When they looked at what fuel was left, they realized they wouldn’t have had enough fuel for a go-around. That’s how tight it was and the closest call he ever had. —DOC GIFFIN

TRICK OF THE KING

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As his assistant for more than 50 years, I flew a lot with Arnold Palmer. In the early days, I had a habit of going to the cockpit and kneeling in the aisle right behind the pilot and copilot to watch what was going on. During one occasion in his first plane, the Jet Commander, Palmer played a trick on me. He was in the left seat, flying the plane, and without warning pulled the controls fully and did a 360. Whoop—I never moved off the floor. That’s how fast it happened. Then he just looked back at me and smiled. I think all I said was, “Whoa.”

I got a real kick out of that, but I think he loved it more. He once pulled the same trick on his manager, Alastair Johnston. As Johnston recalls, “I was sitting in the back reading the Wall Street Journal, and I saw Palmer sort of lean over and say something to the copilot, so I knew something was up. Over we go, and I never looked up from the newspaper. I pretended like nothing had happened. I wasn’t going to react for him.” —D.G.

THE GREATEST DAY

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They said it couldn’t be done. Even the fastest jet cannot eclipse the speed of the Earth’s rotation. Yet on May 16, 2020, arguably the greatest day in golf was consummated: Pine Valley, Augusta National, Cypress Point Club—then as now ranked 1, 2 and 3 on Golf Digest’s America’s 100 Greatest—in a single day. Two foursomes (most titans of their occupations, some merely very successful) teed off at Pine Valley at 5:09 a.m., some with glow-in-the-dark balls. The sunrise in purplish glory above the ridgeline at the ninth was an unfamiliar sight. They walked off the 18th green at 7:15 a.m., and the wheels of the van were in motion by 7:20. Each transition of the day needed to be seamless, and as anyone who has flown privately will attest, it’s the avoidance of rental-car returns, check-in lines, security and other common travel hassles that is the true luxury. On the flight from New Jersey to Georgia they had breakfast and changed their shirts and socks. At 10:29 a.m., they teed off at the home of the Masters for swift yet splendid rounds of three hours and 20 minutes. Back in the air, this assemblage of mostly senior golfers had lunch and indulged in massage guns and heating pads. Fighting headwinds but gaining time all the way to California, golf at Cypress Point commenced at 5 p.m. The final putts dropped at 8:12 p.m., precisely sunset, though 10 to 15 dusky minutes remained had they needed it. For dinner in the clubhouse, everyone had the burger. If all the rushing disturbs one’s sense that the game in great places should be savored, know the feat was bookended by unhurried rounds the evening before at PV and the morning after at CPC. —M.A.

AIR SICKNESS

When a kind veteran pro found out a promising young player had a coach ticket booked from a tour stop to a major championship, he invited the young player to “ride with me.” When he got to the plane, the young player discovered there were just three other pros on the flight, with executives from an apparel company filling out the cabin. No issue, right? Well, major-championship weeks are like spring break for the C-Suite, and these executives got the party started early. One exec went too hard too fast and regurgitated everything he had just consumed onto the shirt of the young player. This story has a happy ending, though: The young player landed a multiyear deal with that apparel company. We’re guessing that endorsement wasn’t based strictly on the quality of his play. —JOEL BEALL

SPOT THE NEWBIE

A magnanimous plane owner invited seven golf buddies to his private Florida club for two nights. We were to leave frigid New York at a civil hour on Wednesday morning, play 18-36-18, and be home for dinner Friday—as far as work and family were concerned, the ultimate sleight of hand! At least this is how it felt to someone accustomed as I was to predawn security slogs and midnight oversize-baggage-claim stakeouts to play half as much golf. Private aviation is a time warp. The tail number and vague parking instructions were sent via group text on Tuesday evening. A reply-all round of emojis and blasé one-word affirmations followed but no questions. This was an experienced group, and apparently this was all the requisite information. I arrived at 7:10 a.m. for our 7:30 a.m. takeoff, walked the 50 yards from my car to the terminal and discovered I was the first one there. After the man who would turn out to be our pilot wheeled away my golf-travel case, I brewed a complimentary coffee and attempted to wait casually. Everyone else appeared between 7:20 and 7:25, clubs slung on their shoulders. A round of smiles, greetings and fist-bumps ensued as the clubs and duffels were whisked away. As we walked onto the tarmac, there by the wing of our friend’s plane stood seven golf bags like cadets and one black Club Glove travel case on its belly. No hiding who was the first-timer. —M.A.

TURNING DOWN PHIL

On a February Sunday in 2012, Phil Mickelson produced a triumph that likely ranks in soul-deep satisfaction behind only his six major wins. He entered the final round of the AT&T Pebble Beach Pro-Am paired with his forever rival, Tiger Woods. Both have legitimate claims to being the king of the Monterey Peninsula, and their rare head-to-head matchup figured to make for high theater. However, Mickelson stifled the drama by shooting 64, smoking an error-prone Tiger by 11 shots to win the fourth of his five AT&T titles.

Lefty was giddy, drunk on euphoria. How much so? After his press conference, I walked to the podium to offer a handshake and congratulations, to which Phil replied, “Are you going home tonight? You want to fly with us?”

“Home” for both of us was San Diego and where I started covering his career in the early 1990s. We were professionally cordial but hardly close, and that’s why the offer caught me by surprise. A dozen complicated scenarios rolled through my head in seconds, involving filing my story, returning my rental car, journalistic ethics and whether anybody on the plane would talk to me besides Amy.

What eventually came out of my mouth was a mumbled, “Tha-, thanks Phil, but I’ve got to work.” He offered his familiar smile and said, “Cool.” He might have even given me a thumbs up.

I wandered back to my desk in the media center in a daze. The only other writer who heard the offer, Alan Shipnuck, needled me about turning Phil down. I kind of felt like an idiot. I’d never been on a private jet and didn’t know if I’d ever have the chance again. This was Phil’s jet. But I did have the rare opportunity to write about one of the greatest days in a famous athlete’s life. When I hit “send” on the story, I knew I’d made the right call, and my own giddiness carried me and the rental car through the darkness north to San Jose.

Wouldn’t you know it, in my post-offer haze and effort to write a special piece from a special day, I’d taken too long and missed my Southwest flight. The irony made me grin. —TOD LEONARD

ASK AND YOU SHALL RECEIVE

At the 1997 Greater Vancouver Open, Mark Calcavecchia finished first, and I finished second. After we did interviews, the sponsors wanted us to visit with the volunteers and say a few words. Calc says, “Yeah, no problem, but you gotta get us a plane to get home to Phoenix.” Unbelievably, they agreed. Well, this plane was well-stocked, and we drank every drop of liquor on it and stayed up all the way home. By the time we landed, we weren’t in our seats; we’re lying on the floor. The pilot had to step over us to open the door, and our wives were there to scrape us off the floor. I haven’t flown private a lot, but I have to think that was a pretty epic flight.” —ANDREW MAGEE

CAVIAR, CHAMPAGNE AND THE CLARET JUG

We owned a plane for about 15 years, and we didn’t look at it so much as just transportation but more of an extension of our home. When the kids got on the plane with all their things, it was always a very fun time for us, but nothing topped the ride home after the Open Championship in 1994. Sue and I were by ourselves that year, and we took a daytime flight back to the United States. We decided we were going to splurge. We got champagne and caviar, and we set the claret jug on a table and just stared at it. We spent a good deal of time really studying it. We looked at all the names and all the little design features. We were really kind of in awe of it. I can’t think of another trip where we didn’t talk a whole lot or do anything. We just sat there drinking champagne and sort of keeping it company. But no, we didn’t drink out of it. We didn’t think that was right. —NICK PRICE

BUSTING CHOPS

As a staff photographer for Golf Digest, one plum assignment was accompanying Jack Nicklaus and his sons, Steve, Gary and Michael, on a fishing trip to Russia’s Kola Peninsula. Jack was known as an intimidating subject on photo shoots, so I was nervous about spending almost two weeks with him.

Aboard his Gulfstream 5, we all fell asleep shortly after takeoff, but a few hours later as we were cruising over the top of the globe, I was awakened by a smell. Ronnie, our pilot, was cooking lamb chops in the galley and asked if I was hungry. I declined, not wanting to be a bother, but he said he was making them for Jack anyway.

Just then Jack wandered back and started discussing with Ronnie the different methods for grilling meat. He said he wanted his chops medium rare and asked Ronnie how he determined doneness. Jack was dissatisfied with Ronnie’s answer and started to give him a cooking lesson when Ronnie stopped him.

“How many times have I cooked chops for you?” Ronnie said.

“A lot,” Jack said.

“Have I ever not cooked them properly?”

“No.”

Ronnie then said sternly, “Then cook your own friggin’ chops” and walked briskly to the cockpit.

After a long, awkward pause, Jack smiled at me and said, “How do you like your chops, Dom?”

It wasn’t long before Jack and Ronnie were back to joking with each other, and it was easy to see that they enjoyed a great friendship. —DOM FURORE

More from Golf Digest

NO CARS

In 1999, Wayne Huizenga, the South Florida billionaire businessman who owned the Miami Dolphins, Florida Marlins and Florida Panthers, bought the course where “Caddyshack” was filmed, Rolling Hills in Fort Lauderdale, and turned it into Grande Oaks. He hired me as the director of instruction and sometimes would drop in for a quick lesson. Wayne was a huge personality, but he was as down-to-earth as anyone I’ve ever met.

In 2000, Wayne invited me on a golf trip to Ireland: four guys, leaving on Thursday, and this was Tuesday! We flew over on his Gulfstream G4, and before we deplaned at Shannon airport, he handed out cash. As his guests, whoever you were, he didn’t want you to spend your own money.

From Shannon, a helicopter took us to Dooks Golf Club, and after 18 and a quick lunch, the chopper flew us to our next course, then to our hotel. The next day, same routine: chopper to the first course, chopper to the second, chopper to the hotel. Third day: chopper to course, chopper to airport, G4 to Florida, back home for dinner. Over three days, we played five courses in southwest Ireland and never got in a car! It was a whirlwind for this humble golf pro to experience the air-to-tee lifestyle. —MARK WOOD

MCDONALD’S PITSTOP

One aspect of tour life that’s always amusing are flights to the United States from Asia or Australia. Most of the time, the smaller jets can’t make it directly to the United States or Europe without a refueling stop. Often, that stop is Juneau, Alaska. The airport is small and ideal for a quick 30-minute refuel. The only food available is McDonald’s. Picture this scene: Late on a Sunday night after a tournament somewhere west of the United States, a teenage McDonald’s server is bewildered as plane after plane comes in to refuel, as some of the best golfers in the world line up for Big Macs to go. —JAMIE KENNEDY

TEACHERS ON CALL

One form of conspicuous consumption for ultra-wealthy middle-handicappers is having a top coach on duty for house calls. One such billionaire made a deal with a coach who has worked with major champions to be able to text a lesson request 24 hours in advance. If the coach was free (and, unless he was with a tour player, he always was), the billionaire would send his jet to ferry the coach to one of his various homes for a three-hour lesson block and then fly the coach back to where he needed to be. Once this involved a round trip from New York to Texas and a third leg to London—a circuit of more than 12,000 miles. Conservatively, that makes for a $100,000 golf lesson. “In the private jet world, getting picked up when somebody is on the way somewhere isn’t that big a deal,” says one top coach with a similar working arrangement. “But when they send the plane, and you’re the only passenger, that’s wild.” —MATTHEW RUDY

HEY, WHO INVITED YOU?

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There are countless ways professional golf mirrors the dynamic of high school: assorted cliques, whisper campaigns, varying degrees of envy and resentment. Then there’s transportation. The guys who have their own rides hold leverage over those eying a lift home.

That we’re talking about wings versus wheels and a few more zeroes on the gas bill only tilts the power balance further. Although there have been reports of Ian Poulter irritating Tiger Woods on occasion—such as a clash over Masters attire and Poulter famously suggesting he and Woods were primary rivals—a defining moment was tied to a flight originating in Pittsburgh.

As Woods’ former coach Hank Haney outlines in his book The Big Miss, Poulter secured a ride home to Orlando on Woods’ plane at the conclusion of the 2007 U.S. Open at Oakmont. One problem: Woods didn’t offer.

According to Haney, Woods secluded himself by putting on headphones in his seat at the front of the plane, leaving Haney to talk to Poulter. That’s when a text message appeared on the coach’s phone. It was Woods, who asked, “Can you believe this d—mooched a ride on my plane?” —SAM WEINMAN

FLYIN’ AND FIGHTIN’

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A flight back from a tour event in Japan featured two golfers. One was Ernie Els, the plane’s owner, four-time major champion, doting father and champion of autism awareness. The other was journeyman pro Steve Marino who had met Els only days earlier but had struck enough of a rapport with him that Els invited Marino to enjoy a lively—and liquid—flight home to Florida.

Laughter roared through the cabin for the first few hours until, abruptly, it didn’t. Els asked Marino if he was having a good time. Marino nodded that he was. Then Els pounced. What followed was a series of head butts and punches, the two large men tangling across the center aisle and back. The flight crew was disappointed but not surprised. This was apparently a thing with Els. The scuffle went on for a time until exhaustion set in. Eventually they slept, and then remarkably, when they touched down, they shook hands and parted ways.

The story circulated for several years on podcasts and message boards. Was it true? Eventually, the question was put to the source, and Els confirmed it was.

“We had a lot to drink,” Els said on a 2018 episode of the No Laying Up podcast. “There was a lot to talk about, and we kind of hugged each other. It was a lovefest on the airplane.” Els laughed when referencing his “hug” with Marino. “Nobody got seriously injured. It was all in good fun. It’s just what guys do when there’s a lot of testosterone running.” —S.W.

A NEAR MISS

Ernie Els has had a few close calls in his life in the air, including a flight with Scott Hoch on the way to Augusta, Ga., for a Masters practice round in which the cockpit windscreen shattered in their Learjet. They diverted to Savannah, Ga., and made it in on another plane. However, nothing compared to the near collision on the way to Kohler, Wis., for the 1996 Andersen Consulting World Championship of Golf. Els was one of eight players competing in the International bracket at Blackwolf Run, and he and Michael Campbell were flying together from Florida. “We were coming in on approach, and there was no one in the tower or on the ground,” Els says. “All of a sudden, the plane’s collision alarm went off. We pulled up hard, and I heard the pilot yelling, ‘Divert, divert!’ I don’t know how close we came, but there was a small plane taking off in the wrong direction and heading straight for us. Something like 1,000 yards is considered a near miss, and I don’t know if we were that close, but it was crazy. They wouldn’t tell us exactly what happened, but you knew looking at the pilots that it wasn’t routine.” —DAVE SHEDLOSKI

MALTBIE AND THE GAMBLER

I’ve had the pleasure of a great friendship with Eddie DeBartolo Jr., the owner of the San Francisco 49ers. I’ve flown with him on many occasions. It’s quite nice, as you can imagine. We’ve had some great times on those flights. Once he invited me to go with him to a road playoff game, and it killed me to tell him I couldn’t make it. I had to be in Endicott, N.Y., early the next morning for a meeting. Eddie wouldn’t take no for an answer. I guess he felt like I must be good luck. He promised to get me to New York that evening. I hope he doesn’t mind me sharing this, but we went to the game, and then he arranged for another private plane to take me to New York. I’m like, You’ve got to be kidding me. The kicker is that I get off the plane, and there is a car waiting for me on the tarmac. The plane next to me belongs to Kenny Rogers, the late country music singer. He sees me getting into a car, and he’s yelling to whoever will listen, why he doesn’t have a car. That was a pretty good deal. —ROGER MALTBIE

THE BEST KIND OF FRIEND

I was a member at Caves Valley, and we were to play in a one-day member-guest with Barry Hyde. It was a miserable rainy August day. Nothing was going to happen. I had a friend at Caves, and he called me and said, “OK, what are we going to do today?” We didn’t want to waste the day. He said, “I’ve got the plane; you organize the golf.” Barry and I sat in the grillroom at Caves and looked at the weather map, and it was green all the way to Chicago and down to Tennessee and to the East Coast. We looked at a variety of places, and eventually, Barry said, “You know what? It’s clear down in Florida.” We got in a Lear and took off for Sawgrass, played the Stadium Course, and then flew back to Caves that night. It’s worth noting that this guy is the kind of friend who if he arranged something and couldn’t go, he’d still send the plane. A lot of other guys, if they can’t go, the plane doesn’t go. One time, when I was living in Atlanta, my friend was going to fly from Washington, pick me up in Atlanta, and a few of us were going to play Sutton Bay in South Dakota, then stay at Sand Hills for an overnight, play Sand Hills and then go to Merion. He called me the night before and said he couldn’t make it, but there was never a question that the plane wasn’t going to show up. Sure enough, we played Sutton Bay, we played Sand Hills and then he joined us at Merion. These are the friends you want to have. —GORDON DALGLEISH

THE WRONG SEAT

I was just 17 when my agent, Steve Loy, brought me an unbelievable invitation: a free ride with his client Phil Mickelson on Phil’s private jet from the United States to a European Tour event in Saudi Arabia. Phil’s brother, Tim, and Dave Phillips, co-founder of Titleist Performance Institute, were also on the flight. I had no idea what I was doing. I looked for a security line to go through, but obviously there wasn’t one. I thought I could walk right up to the plane but was sent back to the waiting area.

Once I got on the plane, which was huge, I was most concerned with not bothering Phil, but he was happy to talk to me. We bonded over being lefties, and he told so many great stories, like the time he won the Tucson Open as an amateur after skipping a 3-iron across the water and making birdie on the back nine when his then-caddie, Loy—who was sitting within earshot—had urged him to play it safe. After a while the crew said they could convert our seats into beds so that we could sleep. I happened to be sitting in the chair that turned into the biggest bed. Steve was quick to tell me, “Let Phil take that bed.” Of course, I immediately gave the bed to Phil, who laughed and didn’t make me feel bad about my faux pas.

Phil finished T-3 in the tournament, and afterward we took the jet back to San Diego. Steve had secured another private jet for the two of us to get back to his office in Arizona. By this point, I was getting accustomed to traveling on private jets, sitting in comfortable seats, eating great food and being able to walk around whenever I wanted. However, I had to take another flight to get home to North Carolina. I flew Southwest. That was a buzzkill.

My flight with Phil was the start of a real friendship. Although we play on different tours, we play practice rounds together whenever we can, and we always have a little money game going on. Our stakes wouldn’t buy much jet fuel, of course. —AKSHAY BHATIA

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