BOSTON – As dawn broke over Sturbridge, Red Sox legend Mike Timlin began his 192-mile bike ride, carrying with him his deep nostalgia and love for his late teammate Tim Wakefield. Every turn of the wheel, every hill, was filled with memories of their playing days together, tense finals, and simple moments with the Wakefield family.
Timlin’s goal was not only to make the grueling journey from Boston to Cape Cod, but also to pay tribute to Tim Wakefield, the legendary knuckleball pitcher and two-time World Series champion who died of brain cancer in 2023. Just a few months later, Wakefield’s wife, Stacy, lost her battle with the same disease. The loss left a void in Timlin’s heart, who shared countless triumphs and family joys with Wakefield.

“Tim was more than just a teammate, he was a brother,” Timlin said before setting off. “This 192-mile journey is my way of reminding myself that Tim will never be forgotten – and to help at least one family not have to endure the same pain.”
Along the way, Timlin tackled the sun, wind, and steep hills of Massachusetts, cheered on by thousands of fans wearing Red Sox jerseys and carrying Wakefield’s legendary number 49. The signs of encouragement, the hugs, made Timlin feel like Tim was still with him.
The Pan-Mass Challenge, America’s largest sports fundraising event for cancer research at Dana-Farber Cancer Institute, was where Timlin delivered a powerful message: hope and action can overcome pain. With the support of the community and former teammates, Timlin surpassed his fundraising goal of $250,000, bringing valuable resources to the fight against cancer.
“Mike reminds us that team is more than just numbers on the field,” said coach Alex Cora. “It’s about camaraderie, camaraderie, and being there for each other when times are tough.”
The ride was more than just physical exertion, it was also a message of friendship and kindness. Timlin recalled the laughs in the locker room, the fishing trips with the Wakefield family, and the casual conversations after baseball. “Tim never stopped helping others. He taught me that it’s not about winning games, it’s about touching people’s lives,” Timlin choked up.
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When Timlin crossed the finish line in Provincetown, cheers and tears mixed. He lifted his bike up, looked to the sky, and whispered, “It’s all for you, Tim.” The ride may be over, but Timlin’s mission continues. He promised to continue fundraising and return next year: “Cancer took my friends, but not hope. We ride for the greater good.”
In a baseball world filled with statistics and victories, Mike Timlin’s 192-mile journey is a living testament to the power of friendship, unwavering promise, and the indomitable spirit of a teammate.
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