Reaching the Pinnacle: 500 Wins by Cape Cod League Managers
This article was written by Russ Speiller
This article was published in Cape Cod Baseball League: From College Stars to Big League Futures (2026)
Scott Pickler is the winningest coach in Cape Cod Baseball history and the only one to reach 600 career wins and counting. He has been head coach of the Yarmouth-Dennis Red Sox since 1998. (Courtesy of the Yarmouth-Dennis Red Sox)
As of the end of the 2025 season, four Cape Cod Baseball League managers have found themselves in the exclusive 500+ win club. Each of them exhibited incredible longevity on the Cape, ingratiating themselves not only to their squads but also to their Cape Cod towns. Below is a profile of each of these distinguished gentlemen.
SCOTT PICKLER (1998 – Present)
Record: 620-502-51
On August 1, 2024, Scott Pickler, head coach of the Yarmouth-Dennis Red Sox, became the first Cape Cod League manager to reach 600 career wins when his team defeated the Harwich Mariners, 7-4.1
Pickler has been head coach of the Y-D Red Sox since 1998, having won six Cape Cod League championships (2004, ’06, ’07, ’09, ’14, ’15, and ’16), while also leading the team to nine Eastern Division regular-season win titles. He was inducted into the Cape Cod League Baseball Hall of Fame in 2019 while still an active coach in the league.2
Over Pickler’s 26 years managing the Y-D Red Sox, he’s coached over 100 collegians who went on to reach the major leagues, including Chris Sale, Shane Bieber, Justin Turner, and Buster Posey.3
At the age of 74, Pickler claims he has no plans to retire soon, telling Los Angeles Times staff writer Mike DiGiovanna in July 2024, “Retirement is overrated. Maybe it would be different if I was a great golfer or had a lot of hobbies, but I’m a bad golfer, and this is my passion. I get to go to the yard and make kids better, and it’s so much fun.”4
According to baseball writer and former longtime ESPN TV analyst Peter Gammons, “Pick is a giant on the Cape. He works so hard at it, he’s so competitive, and he always has a lot of really great players. He’s a great hitting coach and a really good teacher.” Speaking of competitive, Jerry Weinstein, manager of the Wareham Gatemen in 2016 and 2019, referred to Pickler as “an all-time great guy,” going on to state that “he will kick your ass and you still like him. Everybody loves Pick.”5
When not on the Cape coaching, Pickler holds the title of the head coach emeritus at Cypress College in California. As one of the most respected veteran community-college head coaches, he has managed the Cypress College baseball team since 1985, leading the team to five state championships and four runner-up finishes.6
Despite the Y-D Red Sox search committee’s feelings that “[w]e don’t want a junior college coach, and we don’t want anybody from California,” Pickler was recommended to the committee by former Los Angeles Times national baseball writer and 2000 Hall of Fame BBWAA Career Excellence Award winner Ross Newhan, whose son, David, played for Pickler at Cypress in 1992 as well as for Yarmouth-Dennis in 1993 and 1994. Pickler was chosen for the head coaching job from six candidates because he promised to build a competitive team and boost the organization’s youth camps, a key source of revenue for the club. According to Gary Ellis, team president of Yarmouth-Dennis when Pickler was hired, “We used to struggle to make $40 a game, and now, on a good night, we clear a few thousand, $5,000 to $7,000 for a playoff game. Pick has been great for the economy here.”7 Pickler has been so great for the town of Yarmouth that he was named resident of the year in 2017, despite the fact that he resided in Yarmouth only during the summers.
Jeff Trundy was manager of the Falmouth Commodores from 1999 until the conclusion of the 2024 season. He was inducted into the Cape Cod Baseball Hall of Fame in November of 2024 and passed away the following month following a lengthy illness. (Courtesy of the Falmouth Commodores)
JEFF TRUNDY (1999 – 2024)
Record: 546-551-31
2024 was a milestone year for Falmouth Commodores coach Jeff Trundy. It was his 30th anniversary in the Cape Cod Baseball League, having started at the Cape as an assistant coach for Cotuit. It’s also the year that Trundy made the decision to retire from coaching on the Cape, which was followed by his induction into the Cape Cod Baseball League Hall of Fame.
In 1997 Trundy was snapped up by the Commodores to be their assistant coach. He was promoted to the head coaching job in 1999. According to Chuck Sturtevant, the Commodores’ general manager who appointed Trundy to the head-coaching position, “Jeff is a true gentleman of the game. His number-one priority throughout all these years has always been what is best for the players, and I give him credit for that. He never did anything that was for himself or recognition for himself, or anything.”8
Retired Chatham Anglers head coach and fellow Cape Cod League Baseball Hall of Fame inductee John Schiffner said of Trundy: “He’s in it for the kids to get better. Winning is important, but he’d rather see a player improve than win a game. He’s that important for these kids, he wants them to have a great experience, play well, and represent themselves and their colleges well. That’s what this league is all about: relationships and helping kids play better baseball and have a great experience. He is the embodiment of that.”9
Never one to claim the spotlight for himself, Trundy described his tenure in the Cape Cod League as “a real privilege to have been part of this league for so long and to have been surrounded by so many amazing people – players, coaches, and friends. It’s truly an honor, but I recognize that many others have contributed so much more. I’ve been incredibly blessed and grateful for the experiences and relationships I’ve had over the years. It’s been pretty special.”10
Though the Falmouth Commodores never won a Cape League championship under Trundy, he was named Cape Cod Baseball League Coach of the Year in 2004, 2016, and 2019. Trundy was also inducted into the Maine Baseball Hall of Fame in 2013.11
JOHN SCHIFFNER (1993 – 2017)
Record: 539-516-24
During his senior year at Providence College, John Schiffner dreamed of having the kind of season that would get him drafted by a major-league baseball team. However, due to a collision at home plate that caused a hematoma in his thigh, Schiffner’s baseball career headed in a different direction.12
Providence College head coach (1960 – 1978) Alex Nahigian took Schiffner under his wing, propelling him to what became a 25-year run as head coach of the Cape Cod Baseball League’s Chatham Anglers, culminating in two championships (1996, 1998) as well as 16 regular-season titles. When Schiffner took over the Anglers, then known as the Chatham A’s, in 1993 they were a last-place club. John turned the team around, guiding them to a 16-7 finish and an appearance in the league championship.13
Schiffner coached over 1,000 players, including 39 first-round major-league draft picks. The list of major-league ballplayers mentored by Schiffner while part of his Chatham squads included Kris Bryant, Evan Longoria, Andrew Miller, and Todd Frazier.14
Never one to shy away from a microphone and referred to by people who knew him as the “summer mayor” of Cape Cod, Schiffner found himself somewhat of a star when he was prominently featured first in the 2001 romantic-comedy movie Summer Catch, in which he was played by actor Brian Dennehy and then later in the 2004 book The Last Best League: One Summer, One Season, One Dream, in which author Jim Collins chronicled Schiffner and the A’s/Anglers during the summer of 2003.
In 1998, to motivate his team, Coach Schiffner told his players that if they turned their mediocre season around, he’d get a tattoo. Chatham won the championship that year and Schiffner honored his promise by having the word “Chatham” along with a cursive “A” emblazoned on his right leg.15
Schiffner was inducted into the Cape Cod Baseball League Hall of Fame in 2018. He described his lengthy tenure in the Cape Cod league as “[the]greatest experience of my life. To see the league and the Chatham Athletic Association evolve and watch the talent level that I was fortunate enough to have coached was pretty special.”16
In addition to his illustrious career at the Cape, Schiffner spent over 30 years in Connecticut as a history teacher and coach of the Plainfield High School baseball team, which he led to 31 state tournaments. He was inducted into the Connecticut High School Coaches Association Hall of Fame in 2017.17
HARVEY SHAPIRO (1994 – 2022)
Record: 512-498-35
Like the other Cape Cod League managerial members of the 500+ wins club, Harvey Shapiro is a Cape Cod Baseball League Hall of Famer, having been inducted in 2020.
A native of New Britain, Connecticut, Shapiro served as an assistant coach for the Yarmouth-Dennis and Wareham teams before cracking his first Cape Cod League head coaching job in 1994 for the Falmouth Commodores. After leading Falmouth to the league championship series in 1996, Shapiro was named manager of the year.18
After the 1998 season, Shapiro stepped away from managing on the Cape, returning in 2003, when he took the helm of the Bourne Braves. In 2009 he led the Braves to their first-ever Cape Cod League championship. He helmed the Braves until the end of the 2021 season, having helped Bourne to 415 wins under his tenure, including 30 playoff victories.19
After 18 seasons managing Bourne, without a contract to continue as Braves manager and not wanting to retire at the time, Shapiro accepted the position of head coach for the Wareham Gatemen during the 2022 season, after which he retired.
Notable major-league ballplayers who played on the Cape for Coach Shapiro included Darin Erstad, Mitch Moreland, and prolific power hitter Pete Alonso, who ironically did not hit a single home run during his 2015 stint with the Bourne Braves.20
When asked what drove his longevity in the game, Shapiro replied, “I just like being on the field and being a coach. I like helping the players and having a small influence on them.”21
Shapiro’s additional honors include induction into the New Britain Sports Hall of Fame in 2014 and the Maine Baseball Hall of Fame in 2019. Before coaching in the Cape league, Shapiro was coach of the Dutch National baseball team, winning the 1985 European Championship.22
RUSS SPEILLER is a graduate of the University of Pennsylvania with a degree in chemical engineering. He currently lives in Cincinnati with his wife and two children. Russ has spent over 27 years working in R&D creating consumer products for the Procter and Gamble Company. As a SABR member since 2023, Russ has contributed his writings to the SABR BioProject, numerous SABR books, and the Turnstyle baseball literary journal. He’s thrilled to be working on his first original SABR book proposal, entitled How We Played the Game: Baseball at Manzanar [1942-1945], slated for publication in the fall of 2026. You can find and enjoy Russ’s baseball writings at russspeiller.substack.com.
ACKNOWLEDGMENTS
Managerial records were provided by Mike Richard, historian for the Cape Cod Baseball League.
NOTES
1 Justin Girshon, “Y-D’s Scott Pickler Becomes First Cape League Manager to Reach 600 wins,” capecodleague.com , August 1, 2024, https://www.capecodleague.com/news/y-d-s-scott-pickler-becomes-first-cape-league-manager-to-reach-600-wins . Accessed September 29, 2024.
2 Girshon.
3 Girshon.
4 Mike DiGiovanna, “‘Pick Is a Giant:’ How Cypress coach Scott Pickler Became a Cape Cod League Staple,” latimes.com, July 21, 2024, https://www.latimes.com/sports/story/2024-07-21/cypress-coach-scott-pickler-cape-cod-league . Accessed September 29, 2024.
5 George Kostinas, “Y-D’s Scott Pickler Elected to Cape League Hall of Fame,” wickedlocal.com, June 11, 2019, https://www.wickedlocal.com/story/register/2019/06/11/y-d-s-scott-pickler/4938216007/ . Accessed September 29, 2024.
6 https://cypresschargers.com/sports/bsb/coaches/scott_pickler . Accessed September 29, 2024.
7 DiGiovanna, “‘Pick Is a Giant.’
8 Kaileigh Grieb, “Beloved Coach Jeff Trundy Inducted into the 2024 Hall of Fame,” capecodleague.com , June 30, 2024, https://www.capecodleague.com/news/beloved-coach-jeff-trundy-inducted-into-the-2024-hall-of-fame . Accessed September 29, 2024.
9 Grieb.
10 Grieb.
11 Grieb.
12 Brendan McGair, “John Schiffner ’77 Leaves Major Imprint on Cape Cod Baseball League,” news.providencecollege.edu , April 18, 2018, https://news.providence.edu/schiffner-77-leaves-major-imprint-on-cape-cod-baseball-league/ . Accessed September 29, 2024.
13 McGair.
14 McGair.
15 Brad Almquist, “John Schiffner Is Cape Cod League baseball,” boston.com, July 19, 2017, https://www.boston.com/sports/sports-news/2017/07/19/john-schiffner-is-cape-cod-league-baseball/ . Accessed September 29, 2024.
16 McGair, “John Schiffner ’77 Leaves Major Imprint on Cape Cod Baseball League.”
17 Jimmy Zanor, “Schiffner Named to CHSCA Hall of Fame,” norwichbulletin.com, September 15, 2017, https://www.norwichbulletin.com/story/sports/high-school/2017/09/15/schiffner-named-to-chsca-hall/18800838007/ . Accessed September 29, 2024.
18 Benjamin Rosenberg, “Bourne to Manage,” capecodtimes.com, June 20, 2020, https://www.capecodtimes.com/story/sports/2020/06/21/hall-bound-harvey-shapiro-reflects-on-time-in-cape-league/114072352/ . Accessed September 29, 2024.
19 Courtney Jacobs, “Cape League: Field Manager Harvey Shapiro Leaving Bourne for Wareham,” https://www.courtneyajacobs.com/articles/cape-league-field-manager-harvey-shapiro-leaving-bourne-for-wareham . Accessed September 29, 2024.
20 Rosenberg, “Bourne to Manage.”
21 Jacobs.
22 https://www.baseball-reference.com/bullpen/Harvey_Shapiro .