Gary Woodland, Brennan Little
Gary Woodland with caddie Brennan Little during the final round of the 2019 U.S. Open at Pebble Beach. Credit: Orlando Ramirez-USA TODAY Sports

Brennan Little, or “Butchy,” as he’s known on Tour, just wrapped one of the most amazing seasons he’s had in 21 years on Tour.

The year included runner-up finishes at the CJ Cup and Sentry Tournament of Champions, but was highlighted most by Gary Woodland’s major championship breakthrough in the U.S. Open at Pebble Beach, the second major Little’s been on the bag for to go along with the 2003 Masters (Mike Weir).

So, in over two decades of caddying on Tour, where might 2018-2019 rank among those seasons?

“It’s right up there as either one or two,” the 49-year-old Little said. “I think 2003 and this year were pretty similar because obviously you always want to be around when guys win majors. It’s definitely right up there.”

READ: Here’s how Amy Bockerstette wound up at Paul and Michelle Tesori’s house to watch her favorite player — Gary Woodland — win the U.S. Open

Though 2003 and this past season each included a major, Little stresses that they were a very different time in his life.

“I think there were a lot of differences,” he said. “I was younger (in 2003), I didn’t have kids, I thought because Mike was playing so great that (winning majors) just happens.”

Then it took 16 years for the next one.

In the immediate moments after Woodland sealed the win on Pebble’s iconic 18th green and the two embraced, celebrating was not at the forefront of Little’s mind.

Of course he joined Woodland as the trophy was being engraved and he walked up the hill from 18 to Pebble’s famous 19th hole, the Tap Room, as Woodland and other players heading for Hartford the next week toasted the moment, but Little had his two sons on his mind.

Tyler, 13, and Hunter, 9, were playing in their youth baseball world series games at home in Dallas that next week starting Monday — 14 hours later — and Little was intent on making all the games.

While celebrations happened from the scoring area where Brooks Koepka, Jordan Spieth and Justin Thomas congratulated Woodland to the trophy engraving to the Tap Room, Little couldn’t fully engage with them as he continued to get updates from his airline for his 7 a.m. flight on Monday out of San Francisco, a good two hours north of his hotel in Monterey.

First he got a text that his flight was delayed, then cancelled altogether. Little at that point was in the Tap Room chatting with Joel Klatt and Joe Buck of Fox Sports, who had just broadcasted the final round.

Of course, the Canadian got them to chat about hockey.

While they were chatting “everybody was passing the Cup (U.S. Open trophy) around and putting all types of beer in there.”

Little’s description of the U.S. Open trophy is funny, as if it’s his profession’s Stanley Cup.

Too bad he couldn’t partake in much of the celebration, because he wanted to get to his hotel quickly and on the phone with the airlines to get the next flight possible back to his boys.

As Little drove back to his hotel, his airline offered flights on Tuesday and Wednesday, but he eventually secured a 3 p.m. flight Monday, missed the first day of the World Series, but made it back late Monday night in time for games on Tuesday at 10 a.m.

When he arrived in Texas, it was easy to realize it was a world away from the golf mecca of Pebble Beach.

“It was pretty funny because my kids were doing their own thing in the world series, there wasn’t a lot of chatter about the U.S. Open,” Little said. “It was more about baseball which was probably good. It’s not like I was at a kids golf tournament. You’re in Texas and it was all about baseball.”

For Little, it’s tough to miss his boys’ games, and with his work schedule he figures he misses close to half of them when he’s on the road.

“I hate missing games, but it’s part of the job,” Little said.

2019 U.S. Open celebration vs. 2003 Masters celebration

The 2019 celebration in some ways is still on hold for Little as he went straight home from Pebble and still hasn’t taken the trophy home to Dallas yet for a party with friends.

“The win is still sinking in, I guess, because now I have more time to think about it here in the offseason,” Little said.

Times have certainly changed from 2003. He’s no longer the 33-year-old who played the first hole at Augusta in the dark with Weir’s lefty clubs after their Masters win and partied with Weir at their rental home that night, then flew with him to Toronto the Monday after to watch his player drop the puck at the Maple Leafs game in his green jacket.

“That was awesome though,” Little reflected.

It was also a bit sentimental that Weir played a practice nine holes at Pebble with Little and Woodland earlier that week.

Weir texted Little throughout the week as Woodland closed in on the trophy.

“He was pretty excited for me,” Little said. “He texted me ‘keep it going, this is great!’”

The first correspondence between winning player and caddie this year was Little asking Woodland what time he would be on the “Today” show on Monday morning so he could DVR it.

U.S. Open Sunday Moments

“I told Gary on Saturday after the round that his attitude that week was so good,” Little said. “He was mellow, didn’t get frustrated, I said you keep that attitude. You could tell there was something special going on. It was a little different than most of the other weeks.”

So, there was no need for a pep talk to start Sunday before the biggest round of Woodland’s life?

“He’s not a pep-talk guy anyways,” Little said. “The times I’ve tried to pep talk him before he’s said, ‘listen, I don’t want a cheerleader.’”

Asked what image stood out the most from Sunday at Pebble, Little was quick to go with the chip from the green on the par-3 17th.

Gary Woodland
Gary Woodland chips on the 17th green as Justin Rose looks on during the final round of the 2019 U.S. Open. Credit: Rob Schumacher-USA TODAY Sports

“As we got to the ball, I was behind Gary and he said ‘we gotta chip this don’t we?’ And I said ‘yep, looks like it.’ I think leaving that chip down there close and giving us a two-stroke lead going to 18 was huge.”

Little knew Woodland was comfortable with that shot because he used to practice it with a former short game coach Randy Smith.

The 35-year-old also had that same shot on 17 green earlier in the week.

Woodland later said he had the confidence to pull off that shot because of what he did on the 14th an hour earlier when his 3 wood second shot on the diabolical par 5 got a great bounce short of the pin and ended up in the fringe and hole high, leading to a birdie.

“That shot’s right up there near the top (all-time),” Little said of the best shots he’s seen in person. “You could lay it up just short of the green, then hit a little pitch but that’s a hard green to hold because it runs away from you.

I always think getting it up around that green is good because it makes it to where you can always make a five.”

The birdie four gave him a two-shot lead with four to play.

“That was a heck of a shot,” Little said, “how he hit it, then where it landed, it all worked out just perfect.”

Always connected to Pebble Beach

Only six caddies can say they’ve looped for the winner of a U.S. Open at Pebble Beach.

Adding his name to that exclusive list is not lost on Little.

“I think winning a U.S. Open is great wherever it is, but Pebble Beach makes it that much more special,” Little said, “It’s one of the great courses in the world.”

For Graeme McDowell’s caddie Ken Comboy, looking back on their win at Pebble in 2010 is bigger to him than any other accomplishment, even being part of the winning match at the 2010 Ryder Cup.

“Pebble Beach will always be our finest hour,” Comboy said. “I will always look back fondly on that, and at a phenomenal venue. It will live forever in our memories.”

Comboy knows Little must have appreciated a second major win.

“I am sure that with the huge gap in time between the two major victories (for Brennan) he was ready and able to appreciate the enormity of the achievement and also the fortune he has had to be part of it!” 

Hoping to head to Presidents Cup

Looking ahead to December, Little would dearly love to loop in his sixth Presidents Cup.

Woodland is hoping for a captain’s pick from Tiger Woods, though, having finished 10th in the official standings. The top eight qualifiers earn an automatic berth.

“But you know, whatever happens happens, it was a great year,” Little said. “But it’s a hard team to make I know that. Tough competition.”