They Just Kept Showing Up: Remembering Mike Greenwell and Tim Wakefield

There are certain players you remember for what they did.

(Al Bello, Focus on Sport/Getty Images)

And then there are the ones you remember for how they made you feel.

Mike Greenwell and Tim Wakefield belong to that second group. Not because they were perfect. Not because they were flawless legends. But because they were human in ways that connected with the rest of us—stubborn, loyal, sometimes overlooked, sometimes doubted, and ultimately brave.

They wore the uniform of the Boston Red Sox at very different times. Greenwell carried it in the late 80s and early 90s, when the team felt perpetually close but never quite over the mountain. Wakefield carried it through the heartbreak of 2003 and into the impossible joy of 2004 and beyond. Different eras. Different personalities. Same quiet backbone.

I still remember the first time I really noticed Mike Greenwell. It wasn’t a towering home run or a SportsCenter highlight. It was the way he stood in the batter’s box—compact, coiled, no wasted motion. He wasn’t flashy. He didn’t have the sculpted aura of a superstar. But in 1988, when he hit .325 with 22 homers and 119 RBI, finishing second in the MVP race, he felt like ours. He felt earned.

There were knocks on Greenwell’s career. Injuries slowed him down. His numbers never quite reached Cooperstown levels. Fenway was restless in those days. Expectations were heavy. He didn’t have the career of a legend like his teammate Jim Rice. Greenwell’s excellence came in bursts, interrupted by back problems and a body that betrayed him too soon.

But if you watched closely, you saw toughness. You saw a player who refused to make excuses. Who played through pain before we fully understood what that cost. Who was asked to anchor lineups that never quite had enough around him.

He was loyal to Boston. That mattered. 

Tim Wakefield was different in almost every visible way. Where Greenwell was compact and controlled, Wakefield was unpredictable. The knuckleball doesn’t allow for control in the traditional sense. It flutters, dances, humiliates hitters one inning and the catcher the next.

Wakefield built an entire career around that pitch. He reinvented himself after being released by Pittsburgh. He arrived in Boston as a curiosity and stayed for 17 seasons. Seventeen. In a sport that churns through arms and egos, he stayed.

He wasn’t always the ace. He wasn’t always the hero. In 2003, when Aaron Boone’s home run ended that season in the ALCS, it was Wakefield on the mound. The image lingered. Boston can be cruel with memory.

But here’s the thing about Wakefield: he never ran from it.

He took the ball again. And again. He shifted roles when asked. Starter. Reliever. Long man. Stopgap. Mentor. He did what the team needed. When the curse finally broke in 2004, Wakefield wasn’t the headline. He didn’t need to be. His fingerprints were already on the foundation.

He won 200 games. He became the franchise’s all-time leader in innings pitched and starts at the time he retired. But if you ask most fans what they remember first, it isn’t the stats. It’s the decency.

The hospital visits. The Jimmy Fund telethons. The quiet way he showed up for people who were fighting battles bigger than baseball.

Greenwell’s post-career life was quieter, more private. He returned to Florida. He raced boats. He stepped away from the daily glare. But whenever he spoke about Boston, there was no bitterness. Only pride.

Wakefield stayed visible. He worked with NESN. He remained a fixture at Fenway. He aged into that role naturally—the veteran everyone trusted, the steady voice.

Both men had imperfections in their careers. Greenwell never reached the statistical heights some predicted after that MVP-caliber season. Wakefield’s ERA was never pristine. The knuckleball giveth and taketh away. There were games you couldn’t watch without holding your breath.

But here’s what I keep coming back to: they endured.

Baseball in Boston is not for the fragile. It exposes you. It magnifies failure. It replays your worst moments in October, forever. Greenwell played in an era when the Red Sox were often good but never quite enough. Wakefield absorbed public heartbreak and came back for more.

And then, after the cheers faded and the cleats were hung up, they faced something far more merciless.

Illness doesn’t care about batting average or innings pitched. It doesn’t care about MVP votes or World Series rings. It levels everything.

When news broke about Tim Wakefield’s diagnosis, it felt invasive, unfair. He had spent decades giving quietly—time, money, presence. He had been strong for so many. Now he was asked to be strong again, but in a different way. And he was. By all accounts, he faced it the way he pitched: Without complaint. Just resolve.

Mike Greenwell’s passing felt like a jolt from another era, a reminder that the players of our youth are not frozen in trading cards. They age. They fight their own battles. They leave us sooner than we’re ready for.

Untimely is a word we use when we don’t know what else to say. It feels too small. Both men should have had more years. More golf rounds. More Fenway ceremonies. More chances to be introduced on Opening Day and wave awkwardly as the crowd stood.

But here’s what stays with me most.

Greenwell never seemed interested in being louder than he was. Wakefield never tried to be more glamorous than he needed to be. They accepted their roles—on the field and off—with a steadiness that feels rarer now.

In a sports culture obsessed with branding and legacy, they built something simpler: trust.

You trusted Greenwell to grind through an at-bat. You trusted Wakefield to take the ball when no one else could. You trusted both of them to represent the uniform with dignity.

Their deaths came too early. There’s no sugarcoating that. Families lost husbands and fathers. Teammates lost friends. Fans lost something familiar.

But neither man appeared to shrink from the end. There was no self-pity. Just the same quiet toughness that defined their playing days.

Baseball has a way of turning players into numbers, into debates, into footnotes in arguments about WAR and Hall of Fame thresholds. Greenwell’s career can be parsed that way. Wakefield’s can too.

But when I think about them now, I don’t think about WAR.

I think about a left-handed swing in 1988 that made a season feel hopeful. I think about a knuckleball floating under October lights and a pitcher willing to carry the weight of an entire city’s frustration.

I think about two men who weren’t perfect, but were present.

And maybe that’s the point.

Not every career needs to be spotless to matter. Not every legacy needs to end in a parade. Sometimes it’s enough to show up, to endure the criticism, to adapt, to give back, and then, when life demands a different kind of courage, to meet it head-on.

Greenwell and Wakefield did that.

They didn’t get enough time. None of us do.

But they filled the time they had with grit, with loyalty, with generosity, with resilience. And in the end, that feels bigger than the box score.

When Fenway is quiet on a random Tuesday in April, when the wind drifts in from left field and the game slows down for a moment, I imagine there’s still a trace of them there. A compact swing. A fluttering pitch.

Not frozen in glory.

Just remembered.

Written by: Tim Hourihan

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