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Come Fan with UsFriday, June 19, 2026

Tim Wakefield, In His Roundabout Way, Reaches 200 Wins

Tim Wakefield has 200 career wins, but the path he took to get there is as odd as they come.

Tim Wakefield of the Boston Red Sox reacts after earning his 200th win after a game with the Toronto Blue Jays at Fenway Park in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
Tim Wakefield of the Boston Red Sox reacts after earning his 200th win after a game with the Toronto Blue Jays at Fenway Park in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
Tim Wakefield of the Boston Red Sox reacts after earning his 200th win after a game with the Toronto Blue Jays at Fenway Park in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)

Almost everything Tim Wakefield has ever accomplished in his professional career has been reached in a roundabout manner. The straightest path is never the Wakefield path, a fitting notion given the unpredictable nature of his signature pitch, the knuckleball. Last night's start, which saw him surrender the lead twice just mere batters after gaining it and allow five runs on two homers en route to career victory 200, was just the latest example of this trend.

Take the start of Wakefield's pro career. One of the reasons he was drafted to begin with is that he set the all-time record for homers in a single season and in a career at Florida Tech, as a first baseman. Wakefield's bat didn't come with him to the minors, though. Wakefield himself cites the switch from aluminum to wooden bats as the culprit, as well as the sheer speed and power that professional pitchers brought compared to college ones. The Pirates didn't immediately give up on their recent draft pick, though, moving him to third base where offensive requirements were and still are lower. The bat never showed up, though, and Wakefield wound up a career .189/.281/.290 hitter in the minors.

A position player that can’t hit at all isn’t going to stick around very long, especially when they were not a top draft pick. Wakefield threw a knuckleball, though, and the Pirates decided to give him a shot on the mound before they cut him loose. He would throw in 18 games in 1989, including one start, and while he had nine wild pitches, two hit batsmen, and nearly five walks per nine, he also struck out 9.5 batters per nine, extending the experiment.

The Pirates moved Wakefield to High-A, and then the rest of the way up the ladder, until finally in 1992, the former first baseman was pitching in the major leagues. The 25-year-old would post an 8-1 record and 2.15 ERA down the stretch for Pittsburgh, and finished third in the Jackie Robinson award balloting for his efforts. He threw two complete games in the NLCS against the Braves, winning both times, but it wasn't enough, the Pittsburgh fell in seven games.

Wakefield’s 1993 did not go nearly as well, and the Pirates ended up sending him to Double-A, and then Triple-A in 1994. He underwent surgery to remove bone chips from his elbow, but didn’t pitch like he was healthy, and was eventually cut from the team during spring training in 1995 after appearing in just one game.

Enter the Boston Red Sox, who had their own rotation problems, and a new general manager used to fixing problems on the cheap in Dan Duquette. Wakefield was signed to a minor-league deal as insurance for a rotation that was potentially relying on the likes of Vaughn Eshelman for innings. Wakefield couldn't have picked a better time, as, during extended spring training, as the Red Sox shared their Fort Myers park with a women's baseball team that was managed by knuckleball great Phil Niekro, with his brother Joe Niekro, also a knuckler, as pitching coach.

Whatever he learned from these masters of the dancing butterfly was worth the stay in Florida, as Wakefield posted a 2.95 ERA over 27 starts for the Red Sox in 1995, a stretch that included six complete games. His career was back on track, and to this day, he’s still in Boston, 17 seasons, 186 wins, and nearly 3,000 innings later.

Wakefield couldn't just stay in the rotation, though, and win 200 games like a normal pitcher. No, the knuckler also spent time in the bullpen, even becoming the team's closer in 1999 after Tom Gordon's year was cut short due to Tommy John surgery. Wakefield has 22 career saves to go along with his 200 wins; he's thrown 78 regular season games in relief.

Even though he has made 122 starts since 2007, his age-40 season, and has another 49 wins under his belt in that stretch, it was rare that he was supposed to be starting. He’s been something of a swingman in his later years, though, due to a nonstop flood of rotation injuries, he always finds his way back to being a full-time starter for Boston.

Wakefield's career as a whole has been productive -- his ERA+ over 19 seasons is 105, so all told, he has been an above-average hurler. This former first baseman, once cut knuckler is also six wins shy of tying all-time greats Cy Young and Roger Clemens for the Red Sox' franchise record for wins; say what you will about how meaningless pitcher wins are as a statistic, but there is just something wonderful about Wakefield's name alongside those others, doubly so when you consider his pitch of choice and former status as a hitter.

His recent work has not been pretty, though. It took him eight starts to go from win 199 to win 200, the longest wait in between in the history of the game. That's just one more odd "record" that Wakefield has, in a career full of them. He's Boston's all-time leader in innings, games started, has more strikeouts with Boston than Pedro Martinez (fewer than only Clemens), is one of the few pitchers in history to notch 2,000 strikeouts with a single team, but is also responsible for 400 homers, the most of any Sox pitcher, as well as 166 losses.

Longevity will do that to you. And while his career path has been about as straight as a knuckler, much like the pitch, in the end, it has gotten the job done. It’s been fun, Tim.

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