Brennan Little, Gary Woodland
Caddie Brennan Little will be a part of his second Presidents Cup in 10 years when he heads to Australia in December with Gary Woodland. Credit: Kyle Terada-USA TODAY Sports

Brennan Little gets to caddie in his sixth Presidents Cup next month after his boss Gary Woodland got a captain’s pick from Tiger Woods last Thursday.

The Canadian, who lives in Dallas, will visit Australia for the first time in his first Presidents Cup since 2009 in San Francisco.

A decade removed, this is a big deal to the veteran.

“I think it will be great,” Little said by phone in between his sons’ baseball games Sunday. “They’re always fun. You get a nice little payoff for a good year to go hang out and it’s always good hanging with the guys, you don’t get that week to week, a team event.”

Little grew up playing organized team sports since age four and says he’s always enjoyed the team environments.

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“I played football right through high school and I played college golf at New Mexico State which is kind of like a team sport as well because you’re practicing together all the time,” Little said.

Heck, the 49-year-old Little still plays some team hockey now just to keep those competitive juices flowing.

Woodland also comes from a big team sports background with baseball and basketball (at the college level), so between the two of them there’s over three decades of team sports experience that should help team USA.

“I think Gary’s dynamics are really good for a team, growing up playing basketball and baseball,” Little said. “Aside from being a team guy I think his personality is great in the locker room, too.

Brennan Little
The 2019 Presidents Cup will be the sixth of Brennan Little’s career, but his first caddying on the U.S. side. Credit: Stephen Spillman-USA TODAY Sports

“He gets along with everyone. Honestly I think he can play with anyone, alternate shot, best ball, or whatever.”

And Little is looking forward to pairing up with the caddies on the U.S. side as well.

From a workflow standpoint, Little doesn’t see this team event as changing his preparation routine versus a regular stroke-play event.

“I think, generally, you’re comparing notes anyways at regular events with your friends and fellow caddies, things like sprinkler heads or some run-outs or if a guy needs a carry,” Little said. “You’re finding some information and a lot of times, we’ll sit down in the hotel room if I’m staying with someone and I’ll go over the yardage book. So, it’s not like you’re holding back information and not giving it to people in regular events.

“But this week we’re going to have 12 guys and we’ll probably all sit down one night and go over it and digest all the information.”

As his first trip to Australia, one figures there will be a lot to learn about a firm and fast Royal Melbourne. Little has a game plan to get to work on it.

“I’ll walk the golf course when I get there and I’ll make sure I’m prepared,” he said. “If you’re not working the matches on Thursday, then you’ll go out in the morning and get the pins, find out some par-3 yardages and whatever guys want.”

There is one thing that the five-time International team caddie misses most about this event in the past decade.

“I think (I miss) just the team camaraderie, the competition is great,” Little said. “Playing match play four-ball or foursomes, you don’t want to let your partner down.

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“It’s just that team atmosphere. You don’t get it in golf very much and to kind of pull everybody together I think it’s a lot of fun and you’re rooting for everyone.”

Little and his former boss, Mike Weir, enjoyed that very team atmosphere and had all of Canada rooting for them in 2007 when the matches were played at Royal Montreal Golf Club.

They even got paired in Sunday singles with Tiger Woods.

“It was great,” Little said. “Our team was behind, but it made it really exciting for us being in Canada and getting Tiger in singles.”

Say what you will about Woods’ struggles in team events, he still owns the most singles wins in Presidents Cup history with six and a 6-2 record.

“The crowd was great, we came down to the last hole, we had gone back and forth. We had him down a couple and then Tiger came back, but that was definitely a match I’ll remember,” Little said.

Weir won it 1 up in Sunday’s fourth match during a week that saw him go 3-1-1 in front of his home country. The U.S. ended up taking that Cup, 19.5 to 14.5.

This year, Weir and Little find themselves on separate sides as Weir serves as one of International captain Ernie Els’s vice captains. Little obviously will be on the U.S. side for Woodland. So what will that dynamic be like?

“Oh the dynamic is fine, we’re still good friends,” Little said. “I talk to him all the time. It is what it is. Let’s face it, he’s not playing and he’d be the first to tell you as an assistant coach he can only do so much. At the end of the day, I hope our team does the best and obviously Gary. To beat them is obviously the goal and I’ll do whatever I can to help Gary play his best.”

Getting Woodland to play well seems a formality for Little these days after two impressive top 5s in Asia at the CJ Cup in South Korea and then the following week at the ZoZo Championship in Japan.

“I had a pretty good idea a few weeks ago and I talked to Gary on Monday or Tuesday,” Little said.

That’s when Woodland told Little that he was getting picked. The pick was made official during Woods’s announcement last Thursday evening.

“I felt pretty confident, I thought he was going to make it anyways, with the two good weeks in Asia and playing with Tiger the last few days at the ZoZo,” Little said. “And finishing 10th in the standings. I would have been shocked if he didn’t make it after those two weeks.”

Woodland will be making his debut in U.S. team competitions, though he did win the World Cup with Matt Kuchar in 2011.

“I knew this pick meant a lot to him, he had talked about it before and a lot of people had talked to him about it. I think when you’re on the Tour to be involved on a team like that, not only is it a lot of fun but it says a lot about your game.”

Little feels fortunate that his player made the event this year because they certainly know the other side of it.

“It’s not a lot of fun when you watch these events on TV if you were close and are not on the team,” Little said.

And as Little heads to Australia the week after Woods’s Hero World Challenge in the Bahamas in early December, he does so knowing he’s headed for the other team for the first time.

“I did all five of my Presidents Cups (2000, 2003, 2005, 2007, 2009) on the International team,” Little said. “Our record with me working it hasn’t been the greatest (0-5), so I’m looking forward to being a part of this U.S. team this time.”