Last summer, Trevor Wakefield was at Fenway Park selling 50/50 raffle tickets for the Red Sox Foundation. Boston Globe reporter Peter Abraham confirmed it in a July 7, 2025 notes column. Trevor issued no statement about it, gave no interviews, and was simply there doing the work.
That detail is, in a lot of ways, the whole story.
Tim Wakefield’s son is 21 years old. He lost both his parents to cancer before he turned 20. He entered a religious order before most of his peers had declared a college major. He walked onto the most storied infield in New England baseball in April 2024, held his father’s 2004 World Series trophy, and did not say a single word to a camera. And then, the following summer, he was back at Fenway for another reason entirely: the foundation his father spent years building.
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Growing Up in the Wakefield Home
Trevor Wakefield is the eldest child of Tim and Stacy Wakefield. He was born in 2004 in Melbourne, Florida, the same year his father helped the Boston Red Sox end an 86-year World Series drought, and grew up in Hanover, Massachusetts during Tim’s years with the team.
A 2012 Associated Press photograph from Tim’s retirement press conference in Fort Myers shows the family clearly: Tim crouching to hug a seven-year-old Trevor, with Stacy and four-year-old daughter Brianna Wakefield watching alongside. It is one of the few documented public images of Trevor from childhood.
The household was not built around baseball celebrity. Tim Wakefield served as Honorary Chairman of the Red Sox Foundation, helped raise more than $10 million through charitable events, and made annual Christmas visits to the Jimmy Fund Clinic at Dana-Farber with Stacy and their children. Lisa Scherber, the clinic’s Director of Patient and Family Programs, had known the family from those visits for years. She later described Tim and Stacy as “the passionate power couple” who lit up while helping others and who were deliberate about raising their children to understand the value of showing up for other people.
Trevor attended Boston College High School, where he served as a campus minister and was first introduced to the Jesuit tradition. From there, he enrolled at Providence College in Rhode Island, a Catholic institution operated by the Dominican Order of Preachers. He graduated in May 2021 with a Bachelor’s degree in Theology and Spanish, one of only a handful of students in his class to choose theology as a major.
Why Trevor Wakefield Joined the Dominican Order
Three months after graduating, in July 2021, Trevor entered the Dominican Order as a novice at St. Gertrude’s Parish in Cincinnati, Ohio. That November, he spoke to Rhode Island Catholic, in what remains the only public interview he has ever given.
He had considered priesthood since childhood, he said. Boston College High School gave him a close view of the Jesuit tradition. At Providence College, he discovered the Dominican one. His spiritual director recommended a biography of St. Dominic, and reading it resolved the question.
“His energy and compassion almost made him feel like a new, unexpected father figure for me.” — Trevor Wakefield, Rhode Island Catholic, November 2021
He also credited Father Michael Weibley, O.P., the associate chaplain at Providence College, with making it concrete for him: watching how much impact a single friar could have when working inside a committed community was, he said, what moved him to take the next step.
Novitiate life, Trevor explained in that interview, was built around the Liturgy of the Hours, the Rosary, and monastic living. The formal academic phase of Dominican formation was to follow at the Dominican House of Studies in Washington, D.C., where student brothers spend several years in philosophy and theology before ordination. He was at the very beginning of a process that typically takes seven to nine years.
His sister Brianna, a year younger, remained more publicly visible. She maintained an active presence on social media and continued the family’s charitable work in Boston.
Two Diagnoses, Five Months Apart
In late September 2023, it became public that Tim Wakefield had been diagnosed with aggressive brain cancer. The disclosure came largely because former teammate Curt Schilling mentioned it on a podcast before the family had made any announcement. Tim died on October 1, 2023, at age 57, on the final day of the MLB regular season.
What was less widely understood at the time: Stacy Wakefield had already been diagnosed with pancreatic cancer and was already in active treatment.
Two months after Tim’s death, in December 2023, Stacy still made the family’s annual Christmas visit to the Jimmy Fund Clinic at Dana-Farber. Lisa Scherber was there. She later told reporters that Stacy sat in the background, too ill to walk the wards herself, while Brianna led the rounds alongside Santa Claus. “She struggled to get in here and make it happen,” Scherber said. “She knew this was important for Brianna to do.”
Stacy Wakefield died on February 28, 2024, at age 53, at her Massachusetts home, surrounded by family and close friends.
The family released a statement through the Red Sox organization:
“The loss is unimaginable, especially in the wake of losing Tim just under five months ago. Our hearts are beyond broken. We feel so lucky to have had her in our lives, and we take comfort in the fact that she will be reunited with Tim, the love of his life.”
Red Sox manager Alex Cora told reporters at spring training: “She was very strong. She was there for him and now we’re here for the kids. That’s the most important thing.”
Pitcher Jon Lester, a cancer survivor who won two World Series alongside Tim, said at the time: “I can only imagine at my age now, losing both my parents in five months. But I hope they know they have the family here with the Red Sox.”
Jason Varitek left spring training and returned to Massachusetts personally to be with Trevor and Brianna.
Trevor was 19 years old. Both his parents were gone.
April 9, 2024: Back at Fenway Park
The date 4/9 matched Tim Wakefield’s jersey number 49. Whether intentional or not, it was noted by nearly every reporter in the building that day.
The 2024 Red Sox home opener was organized as a 20th anniversary celebration of the 2004 World Series championship and a formal tribute to Tim and Stacy, alongside former team president Larry Lucchino, who had died on April 2. More than 40 members of the 2004 roster attended, including Terry Francona, David Ortiz, Manny Ramirez, and Johnny Damon.
A 2004 World Series banner dropped over the Green Monster. Don McLean’s American Pie played over the Fenway speakers while a tribute video ran on the center-field board, ending with an extended remembrance of Tim and Stacy. When the video finished, the 2004 team walked out from behind that banner.
Leading them onto the field were Brianna and Trevor, both wearing their father’s No. 49.
Johnny Damon placed the 2004 World Series trophy in their hands. Brianna threw the ceremonial first pitch, a knuckleball, to Jason Varitek, who had confirmed by text the night before that he would be catching. Varitek pulled her into a long embrace on the mound after catching it. Trevor stood alongside his sister and together they raised the trophy in front of the assembled 2004 team.
Damon said after the ceremony: “Those kids are going through a lot. They know that they have a lot of family on the team that we had in 2004 and they can always count on us.”
Pedro Martinez, in an exclusive post-ceremony interview with People magazine, described the day as full of “mixed emotions” and was direct about what the team had committed to: “We’re here to be uncles. Close uncles that are going to take care of ’em and anything they need.”
Orlando Cabrera watched Brianna and Trevor from the field and said: “Sometimes there’s just no more words to describe what happened. But those guys have been so good to them.”
Fans received commemorative heart-shaped navy pins featuring Tim’s No. 49. The Red Sox wore a matching heart-shaped No. 49 sleeve patch on their jerseys for the entire 2024 season, recognizing Tim’s long role as the Foundation’s Honorary Chairman.
Trevor Wakefield in 2025
By the summer of 2025, Trevor was back at Fenway on a regular basis.
Peter Abraham’s July 7 column in the Boston Globe noted: “Trevor Wakefield has taken up his father’s legacy and is working at Fenway Park selling 50/50 raffle tickets to support the Red Sox Foundation. Keep an eye out for him at the park.” It was one sentence, written in passing, in a broader Red Sox notes piece. The column also mentioned former teammate Mike Timlin riding in the Pan-Mass Challenge in Tim’s honor — two people, in different ways, carrying the same commitment forward.
On July 26, 2025, Trevor registered as a participant in the 16th Annual Run to Home Base, a Red Sox Foundation and Massachusetts General Hospital fundraiser that runs through Boston and ends by crossing home plate at Fenway. The race raises money for veterans dealing with PTSD, traumatic brain injury, and related conditions. His personal fundraising page on the official event website included a written statement about the cause in his own words.
The Red Sox Foundation also launched the Tim Wakefield Volunteer of the Year Award in 2025, given annually to outstanding youth baseball and softball volunteers from each New England state. Winners were recognized at Fenway Park on September 27, 2025. The Foundation’s website continues to carry this: “Our Honorary Chairman Tim Wakefield and his wife, Stacy, were inspirations and true champions of the Foundation and its mission. We will continue to honor the life and legacy of both Tim and Stacy through our work in the community.”
Trevor Wakefield has not given a public interview since November 2021. He has not issued a statement about any of his activities. What the public record shows, as of March 2026, is a 21-year-old who has been present at Fenway in some capacity every summer since his father died, connected to the same charitable work his parents gave so much of their lives to.
The Wakefield name has carried weight in Boston for more than three decades. At 21, Tim’s son is working out what that means going forward, entirely on his own terms.
Sources: Rhode Island Catholic (November 2021), Boston Globe, ESPN, Associated Press, WBUR, Boston.com, CBS Boston, People Magazine, Red Sox Foundation.
