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Undercover Caddie: The best loopers on the PGA Tour right now

May 30, 2023
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Illustration by Jack Richardson

One of the dumbest knocks we hear on a recurring basis is, “You know what makes a great caddie? A great player.” Well, that’s nonsense. There are a ton of caddies who have taken their players to another level as well as ones who have weighed their players down. I realize a list of bad caddies might be juicer (I need a few beers in me to get those names out), but let’s stick with the good ones. I’m going to fill you in on a “greatest caddies” ranking that a friend and I were putting together recently. These are guys currently looping on the PGA Tour, so we don’t discuss the likes of Peter Coleman (Bernhard Langer), Fanny Sunesson (Nick Faldo), Herman Mitchell (Lee Trevino) and Andy Martinez (Johnny Miller). Furthermore, the No. 1 spot belongs to Jim (Bones) Mackay, and this column already covered why he’s the best, so we’re going to focus on the best of the rest.

Paul Tesori

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Ben Jared

Let’s start with a recent example of a caddie making a positive difference. Cam Young brought on Tesori and instantly almost won the WGC Match Play, and the two followed up with a T-7 at the Masters. To me, Tesori is the total package. He’s a former tour player, so when he speaks to his guy, the voice is coming from someone who has been in those shoes. He does his homework. Remember, he worked for Vijay Singh,and the Big Fijian does not suffer fools. Tesori always tries to see the positive in a situation, and players need that type of reinforcement. He is a social chameleon. Just look at his former bosses: Singh, Sean O’Hair, Jerry Kelly, Webb Simpson, Young. Those are five different dudes with personalities that range from personable to aloof to cold to goofy (in no particular order).

Tesori is an upstanding guy, which goes a long way in the caddie barracks. When he was taking the Cam Young job, he called Chad Reynolds, then Young’s caddie, to let him know. Tesori didn’t need to do that, but he did because he’s the type of guy who wants to do things the right way. When young caddies ask me for a role model, I point to Tesori.

JJ Jakovac

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Michael Reaves

JJ has been a caddie for only 12 or so years, which is a puppy in caddie years, but even before he hooked up with Collin Morikawa, JJ was legit. It’s no coincidence that Ryan Moore’s best run of his career was with JJ. Having JJ on the bag is having a voice of reason in your ear at all times. If you go to a tournament practice round and hang around later in the afternoon, you’ll see JJ roaming the course, trying to pick up any piece of intel he can. A number of caddies do this type of legwork before an event, but I don’t know if any do it as consistently and thoroughly as JJ. That’s part of the homework, sure, but when JJ gives his piece of advice, a player knows it’s not an opinion but based off his research. That means a lot because players don’t care for opinions.

Brett Waldman

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Andrew Redington

A bunch of great loops for whatever reason haven’t reached the same level of fame as the guys casual fans recognize. For me, Waldman epitomizes that group. I’ve lost count of how many players Waldman has worked for in the past 20 years, and I’m sure he has, too. That might have a stigma to it, but I look at it as a positive because the reason he sticks around the tour going from bag to bag is because players know he’s good at what he does. He’s another former player (are you noticing a pattern?) and an astute tactician. Having him inside the ropes is like having a computer simulation giving a player real-time readouts of every scenario involved with every shot. He helped guide K.H. Lee to a win at the 2021 Byron Nelson, and he had Daniel Berger going in the right direction last year before injuries knocked Berger out. Last I saw he’s with Stephan Jaeger; don’t be surprised if Jaeger picks off a top-five finish at some point this summer if Brett is with him.

Steve Williams

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Ross Kinnaird

My fellow caddies likely just swallowed their gum seeing Williams’ name. He is, to put it lightly, a divisive figure among our ranks. Part of that could be envy; he is one of the most famous caddies because of his time with Tiger Woods, and he’s unquestionably the wealthiest. He also holds himself in high regard. He thinks he’s part of the show, so to speak, and that tends to rub caddies the wrong way. That type of conviction was needed when working for Woods. It took stones to challenge Woods, which Williams did, and Woods expected a certain type of professionalism that Williams always upheld.

Here is an unpopular opinion: Fans didn’t like Williams because he could often be a brute to galleries, but things were always crazy around Tiger, and marshals were rarely prepared for the crowds. If Williams didn’t protect Tiger, no one would have. Williams’ approach to things doesn’t work for everybody. His short-lived marriage to Jason Day was a mismatch; Jason was at a vulnerable place that needed affirmation, even a bit of cuddling, but Stevie went drill sergeant on him thinking tough love would do the trick. That said, I personally don’t think Adam Scott wins the 2013 Masters without Williams and his stubborn will on the bag.

Michael Greller

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Kevin C. Cox

Greller is the spiritual successor to Bones. I know the conversations between Greller and Jordan Spieth make for good TV, but the next time you watch, really listen to Greller because he can say a lot by saying little—or nothing at all. That’s a point all of us hope we can reach. Some folks believe Greller needs to challenge Spieth more, but that misses two obvious points: (1) He already does that often, and (2) Part of what makes Spieth so good is he plays with a wild imagination. On the latter point, Greller knows as well as anyone that whatever short-term gains could be attained by reining Spieth in will be negated by the long-term effects of taming that curiosity and creativity.

From a personality standpoint, Greller is an Alpha who doesn’t need to let anyone know he’s an Alpha, who is liked and respected by all because he treats everyone as an equal. If he and Spieth ever split up, there will be a bidding war for Mike’s services, including the broadcasters.