Kessler Karain, Patrick Reed
Patrick Reed and caddie Kessler Karain will soon be headed to Australia for the Presidents Cup after Tiger Woods selected Reed with one of his captain’s picks. Credit: Stephen Lew-USA TODAY Sports

Kessler Karain has been on the bag for his brother-in-law, Patrick Reed, for six years.

Perhaps some of Reed’s self confidence has rubbed off on his looper.

As they enter their sixth team event next month at the Presidents Cup, the overall expectations for Team Reed as a pick for the first time are sky-high.

“Obviously we both want to step up to the plate and show why we were picked, for sure, and we expect to win every match, there’s no doubt about it,” Karain said. “And that way if anyone has any doubts, we can say we put up the points and we won every match, we basically pulled our weight, and if you got anything else to say then speak to the numbers.”

Expecting to win every match, without a doubt, seems to add pressure to Reed and Karain. Does the six-year veteran looper feel that pressure?

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“I think, for me, there’s always a ton of pressure because you’re caddying for a guy named ‘Captain America,’ so you’ve got to win,” Karain said.

“Every shot is just a little bit more important. Every match is just a little bit bigger. Every hole, down to everything. Every decision becomes a little bit more important.”

With the bigger decisions also comes a bit of nerves and emotion.

“If you weren’t nervous then you probably weren’t ready, and if you’re not afraid to make a mistake then you probably don’t care enough,” Karain said. “So I have all those challenges going on, but at the end of the day you’ve just got to go through your processes and trust your instincts and do what you’ve been doing and make the calls that you probably would make whether it was a normal event or the Presidents Cup.”

Karain is thrilled to be back in the team atmosphere with Reed.

“For me, it means a lot because I love those team events. Once you’ve tasted one you always want to be there,” Karain said.

It’s also a good opportunity to come together with other caddies and make a week of fun memories.

Patrick Reed, Kessler Karain
Patrick Reed and caddie Kessler Karain are no strangers to team competitions. Credit: Ian Rutherford-USA TODAY Sports

“You love the camaraderie, and from a caddie perspective with your caddie teammates you get a good time to bond with them and you’re with these people for five or six days and you all have a common goal, whereas most weeks everyone has the same goal and that’s to win, and we’re all out for ourselves,” Karain said. “That’s just something you can’t replicate anywhere else other than these team events.”

During the week’s downtime, players often play ping-pong against each other. The stories of Matt Kuchar’s dominance are plentiful among players the past several years.

Depending on the circumstance, these matches can take on a life of their own with special invited participants.

Jason Day told The Caddie Network that the last time Royal Melbourne hosted the Presidents Cup in 2011, Australian tennis star Lleyton Hewitt joined in on the ping-pong matches.

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“He kicked my butt,” Day laughed.

While the players have ping-pong, the U.S. caddies often find their own ways to entertain themselves.

“A lot of times we all intermingle and relax and watch sports, but in Korea (2015) one funny thing is we got Austin Johnson and Chris Kirk’s caddie at the time, G.W. Cable, to sing ‘Total Eclipse of the Heart’ by Bonnie Tyler because that was their first Presidents Cup,” Karain laughed. “That was a cool thing because it was just caddies-only and they had to sing it.”

Sounds like a tough chore to get those two to buy-in, but the other 10 caddies had a plan.

“We convinced them that it was something that Presidents Cup rookies always do, but honestly they were the only guys who have ever done it,” Karain said. “So it was kind of a big joke we played on them.”

So how did those freshman caddies do on the tune?

“They totally killed it and did a great job,” Karain said, “not because they have great voices but because they were committed to it and they sold it. It’s not like they were up there and they hated every minute of it. They went for it and they definitely sold it pretty well.

Tiger Woods, Kessler Karain, Patrick Reed
Kessler Karain tells TCN that he expects Patrick Reed to win every match U.S. captain Tiger Woods puts him in at the 2019 Presidents Cup. Credit: Jim Dedmon-USA TODAY Sports

“The next year, we were trying to get it to happen and it didn’t happen so it was the only year that it ever worked. I’m sure we’ll try to do again this year for any rookies that will be there because it’s just fun.”

Karain found out he would join this year’s Presidents Cup team with Reed via a text message from his boss three days before the official announcement from Woods.

Karain felt elated, but still harbored some trepidation because nothing was set in stone yet.

“You don’t want to say anything because, one, you don’t want to jinx it; and two, you just don’t want to say anything because it wasn’t official yet,” Karain said.

Reed’s strengths in matchplay

Between the Presidents Cup and Ryder Cup, Reed holds an 8-5-3 record in the these events’ team, match-play formats. Karain attributes this to a couple strengths these stages bring out in his player.

“He gets hyper-focused on everything, every shot means so much more,” Karain said. “I think he also feeds off the crowds more, too. Maybe in team formats, when someone depends on him, he seems to execute a little better for some reason.”

And Karain sees his player as a good match for many of the teammates to pair with next month.

“He’s also a really good partner for most guys because they all know how good his short game is, you could put him anywhere (off the green),” Karain said. “Just put him wherever and chances are he’ll at least give you a really good look for par. He could get up and down from a mailbox.”

Caddie role changes based on format

For Karain, he’s had to learn his role in these team events versus regular stroke-play events.

“When it’s foursomes, caddies kind of take a back seat as far as decision-making in my experience,” Karain said.

He most prominently points to Reed’s pairing with Jordan Spieth for 2014-2017 in Ryder Cups and Presidents Cups.

“In foursomes, a lot of times it’s been Patrick and Jordan and it’s kinda weird for Michael Greller and I because we almost take a back seat because Patrick and Jordan have always had good communication that it’s almost like they’re working together and Greller and I are there to do club selection,” Karain said. “But Jordan and Patrick would literally talk out almost every decision together. Even when it was best ball, and they’re both in the fairway, they’d ask each other what they thought and even though Michael and I are like, ‘we helped you get here, why are you asking him?’ it’s funny and that’s just how it was.”

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In alternate shot, Karain says he has more discussion with his player and that typically they are more aggressive on their putts in stroke-play events versus in alternate shot.

And on approach shots, Karain says they normally give their partner the option between the aggressive shot they’re thinking about and the safe choice and let the teammate decide.

“If they say ‘do your thing’ we take the aggressive play,” Karain said.

Globetrotters add Australia to the list

Karain and Reed rack up the frequent-flier miles each year thanks to Reed’s membership with the European Tour in addition to the PGA Tour. The Presidents Cup in Australia will make the 17th country for Kessler to caddie in, and he trails Patrick by one. Reed played the Canadian Open in 2013 while his wife Justine was still on the bag.

“I’m excited about it. I actually have some friends there, so it will be even better. I met them at the Masters a couple years back and I know they’re pretty excited for us to make the team,” Karain said.

“I’m super excited for my first trip to Australia to be for a Presidents Cup. I’ve heard It’s a proper course and a great crowd down there in Australia.”

How will Karain prepare for this course that neither he nor Reed have ever seen in person?

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“Just by how I would any other week, just walk it a couple times on my own, then during the practice rounds we can talk about how (Patrick) wants to play it,” Karain said.

“I could walk it and think ‘this is a 3 wood’ but he’s kind of an aggressive player, so he might say he’d rather hit driver and get it up there, but I’ve heard it’s not one of those courses that you just blast driver all over the place. So we’ll see if that holds true, especially how they set it up with the rough.”

Jet lag certainly factors in to most international work trips, but Karain is ready for a big time change for Australia. In total, it’s a 17-hour difference between his home in Houston, Texas.

But Karain’s not too worried. He says if he does a workout as soon as he gets to his new destination he tends to get adjusted a little better.

“It helps me sleep better which is key,” Karain said.

Whatever you’ve got to do to be at your best for the big stage.