Mike Timlin was home recently when he got a call from Kathryn Nixon, the wife of Timlin’s former Red Sox teammate Trot Nixon. She had planned to suggest an idea to Timlin’s wife Dawn, but when Mike answered the phone she made the pitch to him as well.

What if they all rode in the Pan-Mass Challenge together in honor of Tim and Stacy Wakefield?

“I don’t think she finished her sentence,” Timlin said. “I’m just like yeah, I’m in.”

An 18-year big league veteran, Timlin was teammates with Wakefield in Boston for the last six years of his career. The pair helped the Red Sox win two World Series championships and remained close in retirement right up until Wakefield tragically died of brain cancer in October of 2023.

Stacy, Tim’s wife, also died of pancreatic cancer five months later in February of 2024, a cruel hand for a family that for years had gone above and beyond in their efforts to raise money and awareness for cancer research.

Timlin said he hoped to honor his friend by furthering the cause he’d dedicated so much of his life to.

“He was a great teammate, he was my best friend, a confidant, he was a great hunting partner for me,” Timlin told the Herald this Wednesday. “He was a wonderful example of how to be a Red Sox in that community, and that’s what a lot of guys remember about Tim Wakefield was how you emulate what he did in the community. That’s all I’m trying to do even in a small way, I know I’ll never reach that level but we’ll do what we can.”

Timlin and his wife rode 85 miles from Babson College in Wellesley to Mass Maritime in Bourne on Saturday as part of the PMC, which runs through Sunday and annually raises money to benefit the Dana-Farber Cancer Institute. More than 6,500 riders were expected to take part in this year’s event, which last year raised a record $75 million and surpassed $1 billion in cumulative donations since the event began in 1980.

Former Red Sox pitcher Mike Timlin on a recent training ride to prepare for this weekend’s Pan-Mass Challenge. (Courtesy of Mike Timlin)

Kathryn Nixon and Dawn Timlin have taken part in the PMC before, and this year Mike said he was excited for the chance to participate himself.

“She knows how important it is and she’s pretty excited that I get to see all the water stops, the pedal partners, the things that go along with this,” Timlin said. “That’s what I’m excited for, I’m excited to see the faces and that we’re going to be able to talk to people and kind of hang out. That’s what the whole thing is about, helping out other human beings as much as you can.”

Since his retirement from baseball in 2009, Timlin and his family have lived in Colorado, where they’ve kept up an active lifestyle hiking, biking, skiing, hunting and riding motorcycles. Timlin also served nine years as pitching coach for Valor Christian High School, where his kids attended school, and since the COVID-19 pandemic the family has made an effort to travel all over the world.

Timlin said training for the ride went smoothly, but his wife still warned him that he shouldn’t expect it to be a walk in the park.

“You’re going to have some sore parts and you’re not going to like your bike on Monday,” Timlin said he was told. “We’ll do what we can and have fun with it. She just said enjoy the ride, and it’s not a race, it’s a ride, so that’s what we’re going to do.”

As for this year’s Red Sox, Timlin said he’s kept up with the team as best he can from Colorado and has been impressed with the club’s performance so far.

“It’s good to see some of the young guys coming up and having fun and playing the game, and that’s exactly what you should do at that level,” said Timlin, who won four World Series championships in his career. “It’s a hard level to play baseball at but the talent that these guys have, if they just relax and have fun they’re going to be successful, and that’s exactly what I think they’re doing right now. That’s fun to see.”

 Sox revisit failed talks?

Though Craig Breslow said the Red Sox were willing to get “uncomfortably aggressive” when it came to pursuing an impact player at the trade deadline, the club’s best offers wound up falling short.

But even if Breslow struck out now, that doesn’t mean he shouldn’t try again later.

Addressing the media on Thursday night, the Red Sox chief baseball officer provided two key insights into the club’s deadline approach. One was that no minor league player was untouchable, which presumably means top prospects like Payton Tolle, Jhostynxon Garcia and Franklin Arias were all available. And two, he decided not to deal anyone off the 26-man big league roster, which means Jarren Duran — perhaps the club’s most valuable trade chip — was off the table.

Breslow explained that he didn’t want to risk damaging the club’s odds of contending by weakening one area of the roster to improve another. Even if the Red Sox have a long-term logjam in the outfield, it’s hard to argue that taking Duran out of the lineup would hurt the offense in the short term. Especially after Marcelo Mayer went down, which opened a spot for all of the club’s starting-caliber outfielders to play every day.

But that won’t be a concern this offseason.

Given that Roman Anthony, Ceddanne Rafaela, Wilyer Abreu and Duran are all under team control for at least another three years, the Red Sox have to eventually deal one of them. Duran has always made the most sense given that he’s the oldest of the bunch, so if other clubs were interested in him this past week but Breslow didn’t feel the time was right, it stands to reason he’ll want to engage this coming offseason.

It wouldn’t be the first time he’s circled back on a top target.

Last summer Garrett Crochet was viewed as one of the best pitchers available on the trade market, but the White Sox opted not to deal the left-hander. Then, the following winter, they re-engaged in talks and eventually the Red Sox were able to land their future ace for a premium collection of prospects highlighted by former first-round picks Kyle Teel and Braden Montgomery.

Minnesota Twins starting pitcher Joe Ryan delivers against the Cleveland Guardians during the first inning of a game, Friday, Aug. 1, 2025, in Cleveland. (AP Photo/Phil Long)

The Red Sox reportedly made a late push this week for Minnesota’s Joe Ryan, who like Crochet last year came into the deadline a few weeks removed from his first career All-Star nod. The Twins held on to Ryan even as they sold off seemingly everything else that wasn’t nailed down, but if the Red Sox call back in the winter and offer Duran alongside whatever top prospects they put up before, would the Twins say yes then?

It’s incumbent upon Breslow to find out.

Wrigley awarded All-Star Game

MLB made it official this week, announcing that Wrigley Field has been awarded the 2027 MLB All-Star Game. The game will mark the fourth time the Chicago Cubs have hosted the All-Star Game, and the first time since 1990.

With that, Red Sox fans will have to wait at least another three years before the Midsummer Classic returns to Fenway Park.

Boston last hosted the All-Star Game in 1999, and at this point it’s looking increasingly likely that Fenway will approach the 30-year anniversary of that seminal event before hosting again.

Next year’s All-Star Game is being hosted at Philadelphia’s Citizens Bank Park, and after Wrigley hosts in 2027 the following year’s game could be impacted by the 2028 Olympics in Los Angeles. Having the 2028 All-Star Game on the west coast would make a lot of sense logistically, and San Francisco’s Oracle Park is believed to be the early frontrunner.

The Red Sox won’t be the only club pushing for an upcoming game.

Fans visit as Wrigley Field marquee reads Ryne “Ryno” Sandberg 1959-2025 in honor of the death of Hall of Fame second baseman for the Chicago Cubs, Tuesday, July 29, 2025, in Chicago. (AP Photo/Nam Y. Huh)

The Toronto Blue Jays and Baltimore Orioles have both waited longer than the Red Sox since their last All-Star Games — they last hosted in 1991 and 1993, respectively — and would likely be at the top of MLB’s list along with Boston. The Athletics will vault to the front of the line too once their new stadium in Las Vegas is finished, and if the Red Sox wait drags out long enough the Tampa Bay Rays may eventually work out their own stadium situation as well.

One positive to the ongoing wait is that by the time the All-Star Game does return to Boston, the ongoing Fenway Corners redevelopment project surrounding the park will likely be finished. That would effectively complete the wholesale transformation of the historic ballpark that commenced shortly after the 1999 All-Star Game, which was awarded to the Red Sox in part to serve as Fenway’s swan song.

Three decades later Fenway is still here and more vibrant than ever. Hopefully it won’t be too much longer before MLB brings its signature summer event to showcase just how much has changed, and how much has stayed the same.