Jake Woodford’s 2026 season with the Cubs barely registered in the grand sweep of Chicago’s pitching carousel, but it still ends with an unusual prize. Because he pitched for both Tampa Bay and Milwaukee this year, Woodford is guaranteed to come away from the World Series with a ring.
That’s a pretty strange destination for a pitcher who spent only a blink in Chicago. The Cubs signed him to a big-league deal in mid-July after he opted out of his minor-league contract with the Milwaukee Brewers.
From there, his stint in the organization covered just four appearances total: two for Triple-A Iowa and two for the Cubs. The MLB results weren’t pretty.
In his two outings for Chicago, he gave up three runs on six hits.
A few weeks later, the Cubs moved on and the bullpen wheel kept spinning. Woodford then landed with Tampa Bay in early August, and that stop was even shorter, lasting only one outing. Still, because of the games he appeared in for the Rays and Brewers, he’ll collect a World Series ring no matter how the Fall Classic plays out.
His year overall was rough. Woodford made 19 appearances between Milwaukee, Chicago and Tampa Bay, finishing with a 7.81 ERA and a 4.51 FIP.
The stuff wasn’t missing enough bats, either, as he allowed 14 hits per nine and posted a 1.843 WHIP. Now 29, the former first-rounder should find another landing spot before next season, but the last five years haven’t produced the kind of results anyone would want.
And if you’re a Cubs fan, the rooting interests are simple enough in the 2026 World Series. Most, if not all, in Wrigleyville are behind the Rays for obvious reasons. Both teams are trying to win their first championship, and nobody there wants to see the Brewers be the one to finally break through.
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