Following his initial retirement from the Cape Cod Baseball League back in August 2017, John Schiffner pondered what to do next.

Still on the heels of an illustrious 25-year stint as manager of the Chatham Anglers — one that saw him become the league’s winningest coach, capture two Manager of the Year awards and two league championships — Schiffner was at a crossroads. Since 1990, the Cape had been his only home for baseball, and it was hard for him to imagine coaching anywhere else at that point.

Still, Schiffner knew that there was something more out there for him, one last side quest to complete: Becoming a Division I coach. Fortunately for Schiffner, a bond he had formed earlier in his career came back to help him fulfill that goal. Nick Derba, a longtime friend of Schiffner’s who he’d coached in the past, had just been named the head coach at the University of Maine. He welcomed Schiffner to his staff with open arms just weeks later.

Ironically. Schiffner’s transition to Maine only marked the first chapter of a years-long journey that ended right where it began: Cape Cod. After serving two years as an assistant coach and recruiter for the Black Bears, Schiffner enjoyed over three years of retirement away from the diamond — but it didn’t last. When he heard about his longtime friend and Falmouth Commodores skipper Jeff Trundy losing his battle to cancer ahead of the 2024 season, Schiffner quickly made his return to the CCBL. Now, he’s bringing his legendary coaching pedigree to the Whitecaps’ dugout this year.

When Schiffner first arrived at Maine’s campus before the 2017-18 school year, he didn’t know what to expect. He had stepped into countless dugouts before that were stacked with proven coaches and athletes at every turn oozing with confidence, but the Division I landscape was a completely different animal for him. As Schiffner watched the program assemble its brand new coaching staff, he realized the best way to acclimate himself amid the chaos was to soak everything up like a sponge.

“At that point (Schiffner) had forgotten more baseball than Derba and I knew combined, but he didn’t come in and insert himself right away,” former Maine Assistant Coach Conor Burke said. “He laid back, he watched and asked questions. It was really amazing to see the type of learner he was for those first couple weeks.”

After a brief adjustment period, Schiffner settled into his new role and became known as ‘The Ultimate Player’s Coach’ within the dugout.

His ability to value each of the infielders he worked with as a person before an athlete set a high standard for the Black Bears’ newfound coaching staff. Burke described Schiffner as always remaining cool, calm and collected no matter what scenario came his way during or between games. His relaxed demeanor often helped anchor a young coaching staff that was composed of multiple coaches in their early 20’s.

“We made a trip to Texas Tech together and Coach Derba was about to have their first child, so he wasn’t able to be there and it was just me and Schiff. I couldn’t have done that trip without Schiff,” Burke said. “I was pretty fresh to coaching in my fourth year of D-I baseball, and his ability to help me get through that weekend was unbelievable.”

In his two seasons at Maine, Schiffner helped the Black Bears take minor — yet still important — steps toward becoming a true competitor within the America East conference.

Following back-to-back below .500 conference records, Maine finished 23-24 overall against America East foes across the 2018 and 2019 seasons with Schiffner on board. On top of that, four different Maine batters finished with a plus-.300 average once during Schiffner’s tenure. Chief among them was Whitecaps alumnus Hernen Sardinas (‘18), who’s .298 mark in 2019 led set the pace for the team in Schiffner’s second season there.

Schiffner enjoyed every second of his stint with Maine, but it wasn’t long before the intense schedule began to take its toll on him. As an assistant coach and recruiter for the university, Schiffner usually spent long hours flying and driving himself across the country not only for games, but to also keep an eye on the next wave of potential Black Bear talent that was on its way.

Shevchik said the recruiting weeks he was assigned in the fall and winter were especially vigorous due to how far Maine’s campus was from other targeted schools in the northeastern United States. In the spring of 2019, Schiffner informed the team that he was finally heading off into the sunset for his long-awaited retirement.

“I wasn’t a young guy anymore. I had scratched that itch of coaching at the Division I level, and thought it was time for a younger person (to take over) that can do more than I was giving Coach Derba,” Schiffner said.

For almost the next four years, Schiffner kicked back and enjoyed all that Cape Cod had to offer away from the baseball field. From time to time, he would still check in with his former Cape League competitors over text, or even travel out to watch games once in a while. But for the first time in his life, Schiffner made an effort to shift away from the baseball spotlight and focus on himself.

Early mornings driving to the stadium were now replaced by fishing trips, vacations with family across the Cape and beyond, or even a routine golf outing with close friends. It felt like after so many years of grinding away as a legendary mentor, Schiffner’s baseball journey had finally come to its rightful conclusion. But then, the Cape came calling once again.

Still months away from the impending CCBL season, Schiffner decided to call up Trundy — then the longtime head coach of the Falmouth Commodores — for one of their regular chats in late 2023. It was then that Trundy revealed he was in the thick of a battle with prostate cancer — and he wasn’t winning. Without any hesitation, Schiffner offered to join Trundy’s staff the following season as a jack-of-all-trades coach, largely just to give Trundy the support he needed. Trundy gratefully accepted.

Back in a Cape League dugout for the first time in almost seven years, Schiffner received a hero's welcome. Along with his expected warm welcome back from the Anglers, other teams in the league often took time to come up to Schiff before games to acknowledge how much they respected what he was doing for his struggling friend.

While his baseball knowledge was unmatched, Schiffner’s contributions that year were mostly felt away from the field. In an effort to boost positivity, he often treated the Commodores’ staff to his homemade quahogs during coaches meetings. He was just happy to be there.

At about the halfway point of the season, Schiffner and the rest of Falmouth’s staff decided it was time to discuss the elephant in the room, and informed their players about Trundy’s health. Although the Commodores ultimately missed out on the postseason, the idea they were fighting for their coach above all else fueled the team until the season’s final out.

As Trundy’s condition continued to decline, Schiffner knew that it wouldn’t be long before he’d have to say goodbye to one of his best friends. During Trundy’s final days, Schiffner made frequent visits to his Connecticut hospital where he simply stood by to keep him company. Trundy later died on Dec. 20, 2024, surrounded by his family.

“We had a moment where there was nobody else around and I just tapped him on the arm and said, ‘You’re my hero,' Schiffner said. “What he told me next will resonate with me for the rest of my life. He said, ‘Schiff, I keep fouling off that two-strike fastball.’”

“To be able to spend the last few days with one of your best friends on a baseball field that you love so much, I couldn’t have had a better experience that summer,” Schiffner added.

After processing the loss, Schiffner didn’t think he had any reason to return to the CCBL. But just when he was about to resume his retirement, Whitecaps manager Jamie Shevchik gave him an offer he couldn’t refuse. Of course, this wasn’t the first time Shevchik had inquired about his services.

Ever since Schiffner left Chatham back in 2017, Shevchik had kept the offer on the table for him to continue coaching with his staff in Brewster. The problem? Schiffner wanted a non-committal role — a gray area where he could coach baseball in a more passive role while still having time to enjoy his retirement. Without much pushback, Shevchik met his demands, insisting that he was just happy he would be there in any capacity and that “any time with him was a bonus.”

The addition of Schiffner to Brewster’s dugout has brought in what Shevchik decribes as a “second manager.” Together, the duo has carved out three overarching goals for the team in 2025: Get better, win games, and have the best summer of your life.

For Shevchik, coaching alongside Schiffner is a full circle moment. In his first year on the Cape, the then-Anglers head coach took Shevchik under his wing and became his biggest mentor as he adjusted to coaching summer ball. Many coaches around the league later started calling the Whitecaps skipper “Little Schiff” due to their similar coaching styles.

“He can do whatever he wants to do without ever permission, because that’s how much I trust him. He’s earned that right,” Shevchik said.

No matter how hard he tries, Schiffner just can’t seem to stay away from baseball on the Cape. It will always be a part of him, something that he will forever be able to look back on fondly — and will someday terribly miss. But for now, he’s not thinking about that. Like "Schiff" has done his entire coaching career, he’s just enjoying the ride.

“Between playing, managing, assistant coaching, scouting and administration, it’s like my 51st year with this league,” Schiffner said, “So, I guess I love it.”

Title photo credit: Casey Bayne