GOOD NEWS: “This Ride Is for Wake” – Mike Timlin Honors His Late Teammate in Pan-Mass Challenge
By [Your Name] | The Athletic-style Feature | July 18, 2025
For more than a decade, Mike Timlin delivered clutch outs under the Fenway Park lights. A quiet warrior on the mound, the former Red Sox reliever helped anchor two World Series championship runs, never seeking the spotlight. But this summer, he’s stepping into the public eye for a different kind of mission — one measured not in pitches or saves, but in miles of road and memories.
On August 3rd, Timlin will ride in the Pan-Mass Challenge, a 192-mile charity cycling event benefiting cancer research at the Dana-Farber Cancer Institute. For the 58-year-old, it’s not about personal accomplishment. It’s about honoring one of the most beloved figures in Red Sox history — his late friend and former teammate, Tim Wakefield.
“I’ve been through some hard things in baseball,” Timlin says. “But this ride is personal. It’s for Wake. And for Stacy.”
Wakefield passed away in October 2023 after a private battle with brain cancer. Just five months later, his wife, Stacy, succumbed to pancreatic cancer. The Red Sox community was devastated. Fans grieved, players wept. But perhaps no one outside the family felt it as deeply as Timlin, who shared a bond with Wakefield that extended far beyond the clubhouse.
“We were locker neighbors, travel roommates, spring training partners,” Timlin recalls. “Wake was the guy everyone leaned on — calm, kind, loyal. You knew he had your back.”
That legacy of loyalty is what fuels Timlin now. When the Red Sox Foundation approached him about participating in this year’s Pan-Mass Challenge, he didn’t hesitate.
“I said yes immediately,” he says. “It’s one thing to mourn. It’s another to move in their honor.”
Two Friends, One Mission
The Pan-Mass Challenge isn’t just another ride. It’s a grueling, two-day journey from Sturbridge to Provincetown, demanding not only physical endurance but emotional resilience. Riders cycle through hills, heat, and sometimes tears, all in support of a single cause: curing cancer.
This year, Timlin will don a jersey with “Wakefield” on the back — not as a symbol of loss, but of purpose. His goal is to raise over $100,000 for Dana-Farber in memory of his teammate and Stacy Wakefield, who was an active voice in cancer awareness.
“Stacy was a fighter, too,” Timlin says. “I’m riding for both of them.”
He’s not alone. Dozens of Red Sox alumni, staff, and fans will be joining him on the course. The team has amplified fundraising efforts on social media, and several current players have pledged donations. Alex Cora called the ride “a beautiful tribute,” adding, “It’s what this organization is all about.”
A Quiet Grief, A Loud Tribute
Despite Timlin’s tough exterior on the mound, friends say he’s deeply sentimental off it. This isn’t the first time he’s honored Wakefield. Last season, when the Sox celebrated the 2004 championship team, Timlin wore a black armband embroidered with Wake’s number. He hasn’t taken it off since.
“Mike doesn’t show emotion easily,” says former Sox catcher Jason Varitek. “But this ride — it’s how he processes grief. It’s how he fights back.”
It’s not lost on Timlin that the road ahead — nearly 200 miles of physical strain — mirrors the long, painful road that many cancer patients walk every day. He’s already logged hundreds of miles in training across Arizona’s sweltering roads. But the hardest part, he says, won’t be the uphill climbs.
“It’ll be seeing Wake’s photo at the finish line,” he says quietly. “That’s when it’ll hit me.”
A Message Beyond Baseball
For Timlin, the ride isn’t just about remembrance. It’s about action.
“I’ve lost too many people to cancer,” he says. “It’s time to do something. Wake did everything with heart. I want to finish this ride the same way.”
He hopes his journey inspires others — fans, teammates, strangers — to contribute in their own way, whether by donating, riding, or simply honoring a loved one.
As the Red Sox Foundation gears up for one of its most meaningful PMC appearances ever, Timlin remains laser-focused. “I’ll ride for Wake, for Stacy, for every family in that hospital,” he says. “And I’ll keep riding, every year, until we beat this thing.”