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Come Fan with UsTuesday, July 7, 2026

Tim Wakefield’s Quest For 200 Wins Hits Another Snag

TORONTO, CANADA: J.P. Arencibia of the Toronto Blue Jays rounds second after a two-run home run off of Tim Wakefield of the Boston Red Sox during MLB action at the Rogers Centre in Toronto, Ontario, Canada. (Photo by Abelimages/Getty Images)
TORONTO, CANADA: J.P. Arencibia of the Toronto Blue Jays rounds second after a two-run home run off of Tim Wakefield of the Boston Red Sox during MLB action at the Rogers Centre in Toronto, Ontario, Canada. (Photo by Abelimages/Getty Images)
TORONTO, CANADA: J.P. Arencibia of the Toronto Blue Jays rounds second after a two-run home run off of Tim Wakefield of the Boston Red Sox during MLB action at the Rogers Centre in Toronto, Ontario, Canada. (Photo by Abelimages/Getty Images)
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Just so you know, this piece only "works" if we agree that Tim Wakefield winning 200 games is like any other pitcher winning 300 games. Or 400. Cool?

Wakefield, as you’ve no doubt heard, has been stuck on 199 wins for quite some time.

Of course, he wasn’t really supposed to reach 199 wins. Not this season. He opened the season in the bullpen, hoping for scraps. But with all the injuries, Wakefield’s essentially been in the rotation since early May. He entered this season with 193 wins. He pitched well in his first start but didn’t win, and lost his second. But then came four wins in less than one calendar month.Then two more in July. Just a matter of time now ...

Except we're still waiting. Wakefield's last victory came on the 24th of July, when he beat the M's despite giving up seven runs in 6-1/3 innings. Since then: seven starts and one (excellent) relief outing, three losses and zero wins. He's not been lucky, but he's not been particularly unlucky, either. His highest Game Score in this stretch: 62. His ERA during this stretch: 5.23 (and that doesn't count the eight unearned runs). In the latest debacle, Wakefield left Wednesday's start against the Blue Jays with an 8-5 lead, but the bullpen coughed up the lead (and more).

Tim Wakefield is hardly the first pitcher who’s ever gone through something like this.

Through the age of 28, Early Wynn -- thanks mostly to pitching for the inept Washington Senators -- won only 72 games: 72 wins, 87 losses. Well, also he just didn’t pitch real well. Hardly the profile of a future 300-game winner and Hall of Famer.

But after the 1948 season, the Nats traded Wynn to the Cleveland Indians, and he soon became a star. Ten years later, Wynn went to the White Sox, and in 1962 he recorded his 299th win.

It wasn’t a good season, though: 7-15, 4.46 ERA. Win No. 299 came on the 8th of September. Wynn started three more games that month, but gave up 20 runs in 23 innings and lost all three of them.

Wynn was not, at that point in his career, the most lovable character in the game. Around that time, umpire Nestor Chylak said, “If Early Wynn was pitching every day I was behind the plate, I’d rather join the Russian Army.”

So, stuck on 299. Worse, that winter Wynn turned 43. He reportedly devoted himself to getting in better shape than usual and did get invited to spring training with the White Sox. But just before breaking camp, the Sox cut him. And nobody picked him up until late June, when the Indians brought him back. It wasn’t completely a stunt; the Indians were still a part of the American League pennant race at the time. But getting Wynn his 300th win was certainly on everyone’s mind.

He started on the 21st of June, and pitched a complete game against the White Sox but lost 2-0. He started against the White Sox again, one week later, and went six innings without a decision. His next start came against the Red Sox, and he pitched six innings of scoreless ball but again got a no-decision. After pitching a couple of scoreless innings in relief against the Yankees -- again, no decision -- Wynn's ERA stood at 1.96 but he still hadn't won.

On the 13th of July, in the second game of a doubleheader against the Kansas City A’s, Wynn gave up four runs in five innings before departing. The Indians were ahead 5-4, and would score twice more while reliever Jerry Walker pitched four scoreless innings to preserve the lead. (No word on whether or not Wynn bought Walker a watch, or maybe a pack of smokes.)

it had taken more than 10 months. But Wynn was the 14th major leaguer to win 300 games.

Despite his (then) 2.89 ERA, Wynn wouldn’t start another game for the Indians. Nor would he win again, despite pitching effectively in his 15 relief outings, most of which came in games the Tribe was losing. Once he got 300, management effectively put Wynn out to pasture. And despite finishing the season with excellent numbers, he never pitched again.

Tim Wakefield might not pitch again after this season. He's still a pretty good bet for 200 wins, though. If he stays in the rotation, he'll probably at least luck into one more win. And he might as well stay in the rotation. Considering Clay Buchholz's rehabilitation and Andrew Miller's ongoing struggles, there should be room for Wakefield to start another three or four games, which would tilt the odds in his favor.

Not that it seems to make any difference, but most of us are pulling for him.

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