In his decorated career as a baseball coach, Yarmouth-Dennis Red Sox manager Scott Pickler has guided over a thousand ballplayers.

He was inducted into the American Baseball Coaches Association Hall of Fame and the Cape Cod Baseball League Hall of Fame in 2019. He became the head coach at California’s Cypress College in 1985, and led them to five state championships and four runner-up finishes. “Pick” has been the Y-D manager for over a quarter of a century, including six championship summers between 2004-16. Over 120 of his Cape kids have gone on to the Majors, including Chris Sale and Connor Wong.

In other words, when Pickler says he’s never seen a Cape League outfielder with an arm like the one on Braden Montgomery, it’s a significant endorsement.

“When he came in from Stanford, he was young. Couldn’t believe how talented he was, how big he was, how strong an arm he had, and he was fun to coach,” Pickler told the Herald after the Red Sox selected Montgomery 12th overall in this year’s draft. “I haven’t had an outfielder that threw that accurate, with that good an arm, I don’t think ever at Y-D. I’ve seen him go back at right field almost to the wall, throw a strike to third base, throw guys out at the plate.”

The Red Sox believe Montgomery, who played in three College World Series with Stanford and Texas A&M, can handle all three outfield positions, including Fenway Park’s unique right-field corner.

“He’ll learn to do it,” Pickler said of the Boston ballpark’s tricky dimensions. “If he’s up there long enough, he’ll get used to it, I guarantee you.”

With Y-D, Montgomery also put his impressive arm to use on the mound.

“We did throw him in the playoffs his first year,” Pickler said. “He was touchin’ 96 off the mound against Orleans in the playoffs, and he was dynamic on the mound, but we didn’t pitch him much.”

Some players will do an entire summer down the Cape, others, like Red Sox 2023 first-rounder Kyle Teel, only have time for a short stint. Montgomery spent back-to-back summers with Y-D, so his manager got to see just how much he’d improved when he returned for round two.

“The swing was bigger than it is right now, he swung too big. I thought his freshman year, he made some real good adjustments,” Pickler assessed. “He came back the next year and he was a lot more mature, a better baserunner, his game got a little bit better. He learned to tone down his swing and use the whole field, and it was really neat to see his growth from a freshman to a junior.”

Spending two seasons together also gave the manager insight into Montgomery’s character, especially as the outfielder grappled with the decision to enter the transfer portal after his sophomore year at Stanford and depart for Texas A&M.

“Braden is a good person, and I think he went through a thing where he struggled, because he liked his coach at Stanford and that was a tough time for him,” Pickler explained. “He went on to Texas A&M, and I don’t think that was an easy decision, and he handled it well, I thought.”

Pickler’s self-professed dislike of the transfer portal hasn’t stopped him from keeping tabs on Montgomery.

“I texted him the other day, he texted me back,” the manager said. “I just said, ‘Hey I’m proud of you.’ ”

What Pickler saw Montgomery do in an Aggies’ uniform only bolstered his opinion that the outfielder was meant for the Majors.

“I watched a 12-inning game, because, I don’t know why, but I watched the whole game,” he said. “And his approach at the plate was so good, and I just said, ‘Oh my gosh, this guy’s gonna be a big-leaguer someday.’ ”

That 12-inning bonanza was on Pickler’s mind when Mike Rikard, Red Sox vice president of scouting, sought the Y-D skipper’s opinion.

“I did tell ‘Rik’ that his swing, the day I watched that 12-inning game, man, what an adjustment he made,” he said. “And this guy isn’t missing pitches he used to miss, that’s what I told him, and that you got a freak athlete that’s got an unbelievable outfield arm, and he’s gonna play for a long time.”

Montgomery suffered a broken ankle during the NCAA Super Regional, so he isn’t likely to make his professional debut this season. Pickler has no doubt that once the outfielder gets going, his rise will be rapid, possibly even skipping a few steps along the way.

“It was a crusher when he had that play at the plate. Texted him after that, and found out it was a clean break, so it’s not much that they’re gonna have to worry about, it’s gonna heal and he’s gonna be fine,” Pickler said. “I don’t know where they’re gonna start him, but it won’t be long before he’s in Double-A. As soon as he does well at Double-A, he has a chance to skip Triple-A like some of them do.”