By Ben Strober
86-year-old Jim Gillen remembers it like it was yesterday. Fifteen years ago, Gillen’s wife suggested the two attend a Cape Cod League baseball game just to check it out.
Unfamiliar with the league, Gillen attended a game in Yarmouth-Dennis.
When watching a new baseball team, Gillen closely eyes the manager, from his mannerisms, his decisions, and the respect he shows towards their players.
It seemed like luck, maybe even destiny, that Gillen observed who would become the Cape Cod Baseball League’s winningest coach.
Pretty quickly, Gillen saw what he needed to see; he saw greatness in what Yarmouth-Dennis manager Scott Pickler brought to the table, and the rest is history.
Pickler enters his 25th season with the Red Sox, tying him with former Chatham Angler manager John Schiffner as the longest-tenured manager in league history.
“He’s forever teaching; that’s what he’s doing,” Gillen said. “He teaches these kids the proper way to play wherever this person is playing. It’s absolutely incredible.”
Now, Gillen and Pickler are longtime friends, sharing a gratitude of respect for one another. Additionally, Gillen enters his 11th season as a host family for players and coaches.
“I love getting to know a different group of players every year,” Gillen said. “The Cape is truly special.”
It goes without saying; Pickler is a winner. Instead of defining Pickler as just a perennial winner, he’s defined as an impactful figure that leaves an ever-lasting impression on those around him.
“It’s obvious he’s a fantastic manager and wins,” longtime fan Gary Wilson said. “It’s what he does for these boys every year that stands out.”
At practice, it’s evident Pickler is a teacher. He often walks around offering his insight to his new group of players.
“Whenever he sees something, he speaks up,” Gillen said. “He’s always pulling someone to the side, helping them make adjustments, and the results come shortly.”
As the Cape Cod Baseball League celebrates its 100th year of competition, the Yarmouth-Dennis Red Sox additionally honors another aspect of its history.
Last year, Pickler climbed the Cape Cod Baseball League’s highest peak, moving to the top of the all-time win list as a manager. Now, they further celebrate his quarter-century of managing.
“There’s nothing he hasn’t seen or isn’t prepared for,” pitching coach John Raiola said. “The things we do to prepare and try to accomplish are a lot more than most summer teams.”
Pickler surpassed Schiffner in June 2022, notching his 540th win as manager. That win total further rose to 553 by the season’s conclusion.
It’s evident that coaching is Pickler’s calling in life. Spending his summers in Yarmouth and coaching some of the nation’s best players represents a small sample of his work on the diamond.
In 1985, Pickler took a job managing a struggling program at Cypress Community College in California. He righted the ship and then some.
Pickler’s leadership propelled Cypress to five California state championships, with the most recent coming in 2013. Additionally, he has taken home honors for the California Community Colleges Coach of the Year four times, as well as the Lifetime Achievement Award from the California Community College Athletics Association in 2016.
Pickler’s success in California has translated to his teams across the country. The Red Sox have won six league championships under Pickler, including a three-peat from 2014-2016.
With that success comes the ultimate prize: the respect of others.
Gillen often raves about when he attended Pickler’s induction into the CCBL Hall of Fame in 2019.
Gillen said everyone in attendance wore a suit and tie to the induction.
“What did that do? It showed respect,” Gillen said. “People showed their respect to him and what he’s done in this league.”
Raiola enters his second year with the organization this season. He said Pickler’s impact he leaves on others stands above his prolific baseball knowledge.
“It’s not just summer ball. It’s not just going to get some swings or some innings,” Raiola said. “It’s about showing what you can really do at a high level, and Pickler preaches that message.”
When Pickler took the job in Yarmouth-Dennis in 1998, he only planned on doing it for one year. Quickly, Pickler realized The Cape was his second home.
“When I got here, I got my feel for division one baseball,” Pickler said. “After the first year, they didn’t ask me if I was coming back. I just keep coming back, and now I’ve got family and friends out here.”
Pickler credits his success in The Cape to the board, who consistently provided him with great talent and even better people.
Pickler often reminisces about his early tenure with the Red Sox. He said when he started, Red Wilson Field looked nothing like its current state.
From the bleachers, to the press box, to the many new features offered at Yarmouth games, Pickler is awed by the change.
“The people of Yarmouth have done an unbelievable job of changing the stadium,” Pickler said.
Pickler calls himself “brutally honest” with his players. When he sees something a player is missing in their game, he tells them.
“I don’t sugarcoat it with them,” Pickler said. “I’ll let them know if what they’re doing is going to get them to the big leagues or not.”
Pickler said he doesn’t keep track of it himself, but last time he checked with a board member, at least 120 of his former players made it to Major League Baseball.
“I’ve never told one of my players they were going to be a big leaguer and not seen them make it because I don’t throw that out there very much,” Pickler said. “If he’s got a chance, I’ll tell him and help him get there.”
Over the years, Pickler built strong relationships with MLB scouts, who he said contact him often. And when scouts contact him, they aren’t concerned with a player’s talent; they ask about them as a person.
“I’ve had scouts ask me how a certain player treated their host family, so I tell him exactly how I feel,” Pickler said.
Pickler values players not based on talent but on their makeup.
“I ask coaches for baseball players,” Pickler said. “I don’t care how fast you are, or how strong you are.”
Additionally, Pickler said before choosing his players, he questions the college coach if he’d let the player live in his house. If the coach hesitates, he won’t bring him in,
As the new season approaches, the team begins to practice and familiarize themselves with Pickler’s way.
When Pickler called in a group of players from their warmup in the outfield, they all jogged over with a big smile. Gillen observed the players emotions from the bleachers and said, “You see why they are smiling? It’s cause they get to play for Pickler.”