PGA Tour caddies Kip Henley and Don Donatello dish on the realities of the job
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PGA Tour caddies Kip Henley and Don Donatello dish on the realities of the job

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Outside the ropes, golf is often seen as a gentlemen’s game, one primarily played by affluent and etiquette-conscience elites, of sorts. Crescendos of polite clapping from the galleries await each player after a respectable approach shot or converted putt.

The royal hierarchy inside the ropes has all the optics of an aristocratic affair, the perfect pairing of an immaculate course and everything-in-place athletes with a trove of riches bestowed upon the best golfer of the week. But palace intrigue lies just under a rose-colored veil. If the golfer is the nobleman, everyone around him is a pawn.

The royal class of the PGA Tour strives to literally retain status, cutting out perceived weak links among those in his stable should his ranking be threatened. PGA Tour players have a bit of Marie Antoinette in them.

A PGA Tour player’s inner circle takes a calculated risk to be a part of something larger, knowing that their place at the table hinges on the wishes and success of the player. And nobody is closer to the pros than the caddies.

“Normally the caddie goes first; the second to go is the coach; the third to go is the agent, and then guess what is the fourth to go? The wife or spouse,” veteran caddie Don Donatello says. “And I know it sounds really cruel, but they just find it easier to blame other people than just to be honest with themselves and say, ‘Hey, guess what? I hit a bad shot. I just need to do better.’”

Donatello says there are not many long-standing player-caddie relationships anymore. The splits occur for a number of reasons. Take his 2018 split with Tom Lovelady.

“When you’re spending every single waking day [with a player], sometimes things can get on your nerves,” he says. “One, you could be tired. Two, you know, the pressure of trying to keep your card, especially a young kid like that. He’s a rookie.”

One of the best known -- and jocular -- loopers, Kip Henley, understands the fragile nature of player-caddie relationships and claims there are many broke caddies on Tour.

“Caddies are like underwear. When something goes wrong, you change ‘em,” the Chattanooga native says, adding, “There ain’t a caddie out there that hasn’t been fired. Not one.”

How much do caddies really make?

The no-contract association between player and caddie makes for a risky financial environment.

Despite receiving travel stipends typically ranging from $1,200 to $3,500 depending on the success of the golfer, caddies usually rely on player performance for any additional significant compensation. The Sony Open in Hawaii can prove to be an expensive start to the year, with travel expenses upwards of $3,000 for the caddie alone.

“There’s not five caddies that miss the cut that make money that week,” Henley says. “Honolulu can be a disastrous start to the year for some guys.”

Player-caddie compensation agreements vary, with caddies earning anywhere from as low as 6 percent of a player’s check for a made cut to 10-plus percent for a win. The Valspar hats caddies wear also provide a nice end-of-year bonus. Caddies earn a point for each tournament day in which they participate and can earn more based off player performance. A missed cut will yield just two points for the week, while a win could be rewarded with 18 points. At the end of the year, the money from sponsor Valspar is divided by the number of points to determine the value of each point. This year, points were worth $43 apiece.

“I had 125 points this year, and I had an average year,” Donatello says. Better player performance yields bigger paychecks, of course, and additional hat sponsors. The top tier caddies are making $40,000 to $60,000 from hat sponsorships, according to Donatello.

The caddie lawsuit and the Tour's unexpected resolution

The benefits package on Tour for the caddies has been non-existent in past years, while players enjoy perhaps the best insurance policies and retirement plans of any sport. The lack of benefits has been a point of contention for Henley and other caddies, who have tried suing the Tour in recent years.

“There was enough money going around, and the Tour was helping enough people, but they weren’t helping us so that’s why we did our lawsuit,” Henley says.

Despite having the case tossed out of court twice, Henley praises the Tour for their recent agreement to provide health insurance compensation to caddies and their families.

“It’s a bit of a new regime on the PGA Tour, and for them to come back after we did that and say that they still want to help us, it’s nothing short of a miracle,” Henley says.

Henley believes the Tour may one day provide caddie retirement plans as well if the financial strength continues.

“There’s some good, solid leadership going on on the PGA Tour right now. It’s amazing. We’re grateful.”

Cheating on Tour

Although caddies face immense pressure, players also rely on low scores for high pay. The drive to succeed can lead to players seeking unfair advantages.

“Some of it’s innocent cheating, some of it’s intentional cheating,” Henley says.

He has seen his fair share of it: A player not calling a penalty on themselves if the ball moves after address; tamping down spike marks on the green; improper ball marking; and overestimating how far a ball crossed over a hazard are the primarily infractions Henley has witnessed.

“I’d never name names, but the people that are out there, they know,” Henley says. “They know the guys that are guilty of it quite often.”

Donatello has seen the cheating as well: “ Tour Finals, I worked for somebody, and I can’t mention the name, but I saw the ball positioned one way, and then I looked down and it was in a different spot and I know that same person that I worked for, they hit a ball in the water and it didn’t cross where he said it did. And so he took a drop way up further so that he could still hit it to the green.”

Weather can wreak havoc on a round, perhaps nowhere more than at the British Open. In 2010, when Louis Oosthuizen won on the Old Course at St. Andrews, Donatello and Henley both battled the elements. Henley was caddying for Brian Gay.

“I’ll never forget that day,” Henley says. “Brian Gay teed off in beautiful weather on No. 1 at St. Andrews. It was just an amazing atmosphere, you know. As soon as he hit his tee ball and everyone else in the group teed and we walked off that tee, all of a sudden, it was just like someone flipped a switch.”

Conditions only worsened. The 40-50 mph wind gusts caused blowing rain.

“And by the time we were like five or six holes into it, I had the umbrella out and I swear -- no caddie embellishment -- I had the shaft of the umbrella parallel to the ground.” Henley adds, “I’m like Forrest Gump, I swear it was raining up.”

Donatello and his player, Tim Petrovic, waited out the weather in a van being rattled by the winds.

The job at hand

In spite of dealing with financial worries, cheating and weather conditions, caddies have a job to focus on when they arrive to the course. Donatello says that when he first started caddying, he would check out the course Monday. On Tuesday, he would walk nine holes before playing 18 holes with the player and then walk another nine holes after the round.

“Before we even started Thursday’s round, I would have 54 holes on the golf course or more,” Donatello says, adding that he would take notes on carry lines, best bail-out areas, firm areas and soft spots, and rough length in different areas.

Swing tips are almost always left to the range and instructional coaches, but Henley works closely with player Austin Cook on keeping his ball position and his lines consistent. Perhaps the most crucial thing a caddie provides, though, is confidence.

“The most important thing when a player is hitting [is] that he believes what he’s doing is correct,” Henley says. That means leaving a caddie’s opinions in the bag sometimes.

“Sometimes I can be so sure that I’m right and I feel him out and realizing well, I can tell by his demeanor that he’s not coming on board with what I’m likin’. I got to figure out a way now to make him think he’s doing exactly right.”

When it comes to Cook, Henley explains, “Everything’s his decision, but we work things out together.”

Donatello tells a similar narrative: “I had to be 110 percent sure before I even took anybody off a club or decision because I would rather that player be committed and make a committed swing, than me take a club out of somebody’s hand and make a poor swing.”

Shifting bagmen

Currently Donatello is looking for a bag for the upcoming season, while Henley hopes to continue on with Cook, or “Cookie,” as he affectionately calls him.

Caddies rarely stick with the same player over the course of either’s career. Just check out the Association of Professional Tour Caddies website, and one will find a litany of players under most caddie profiles. Henley served several years for Brian Gay “being his outdoor butler” before a petty money issue temporarily soured the relationship.

“The day I quit Brian Gay, I knew I was doing something stupid, but I was prideful,” Henley remembers of his split with Gay at the 2011 Canadian Open.

The grass is not always greener on the other side.

“I’d had such a good run with Brian, you know. I felt like Tiger would call me the day I quit him.”

The relationship has since been repaired.

Henley says, “Brian was a beautiful boss to me, and his family and me are dear friends to this day.”

After the split from Gay, Henley landed Brad Faxon the week after the Canadian Open at the Greenbrier Classic. While a great bag to carry, he possibly could have had a young, rising star. Henley recalls sitting next to a friend in the caddie trailer that week who mentioned that some guy named Billy Horschel -- who was in his first full season on Tour at the time -- was looking for a caddie. Horschel’s five made cuts in 18 events so far that season did not impress Henley.

“I’m not gonna caddie for somebody I can beat,” Henley told his friend. Three years later, Horschel won the FedEx Cup.

Their Big Break showdown

Henley understands the difficulty of breaking onto the Tour. Henley, who has won the Tennessee PGA Section championship several times, played in around 30 Nationwide Tour events and the PGA Tour’s St. Jude Classic seven times.

“I was 5 under standing in the middle of 12 fairway one year in St. Jude in the first round and I was in second place, and I still managed to miss the cut that year,” Henley says.

Ironically, Henley and Donatello share a famous backstory. Henley won Golf Channel’s Big Break II in 2004 over none other than Donatello. Henley’s wife encouraged him to apply.

“The deadline day, she begged me again and just to pretty much just shut her up, I did it. I filled out the questionnaire and sent it in,” Henley recalls.

Then in his 40s and with bleached-out hair, Henley did not match the typical contestant.

“I think I was just a little bit different than all the great players who were good-lookin’, tall, young guys on the range hittin’ perfect golf shots. I think they chose me just ‘cause I was so different,” Henley says, adding that he “was kinda funny” as well.

The offseason

During the offseason, Donatello plans to work on his own game, teach some lessons to college golfers and spend time with family.

“Didn’t see my family for 14 weeks,” Donatello says of his summer caddying for Lovelady.

And do not be surprised if you call for an Uber in Chattanooga this winter and see a man named Kip drive up to the curb. The always entertaining and rarely predictable Henley says that part-time job may be in the cards this offseason.

The PGA Tour ranks are overflowing with people making a big sacrifice in pursuit of a bigger dream. From players to caddies to wives and families, risk and sacrifice permeate. Perhaps the drive to be a part of something bigger than themselves makes the lifestyle worth it.

“Being inside the ropes around the best players in the world, seeing the best shots,” Donatello says. “It doesn’t feel like I’m playing, but it still feels like I’m part of the game.”

About the author

Michael Holmes

Michael Holmes

Michael Holmes is an avid golfer and owner of a landscaping and mowing business in central Illinois. His passion for journalism emerged from writing for his family’s hometown newspaper during high school and college. A successful high school golf career was highlighted by winning the conference tournament and advancing to the IHSA State Finals. After high school, Michael focused on his academics and earned a Bachelor of Science degree in Horticulture: Production & Management from the University of Illinois. He continues to enjoy playing golf and has won his club’s championship tournament multiple times. When not landscaping or writing, Michael enjoys hanging out with his family and girlfriend and watching sports.