A World Series ring can be the achievement of a baseball lifetime. Players who pick up a glove and a ball when they can hardly walk get the chance to be recognized as champions at the highest level of the sport.
For Jake Woodford, the 2026 World Series comes with an odd guarantee: He’s lined up to get a ring no matter whether the Milwaukee Brewers or Tampa Bay Rays win the title.
It’s an odd fluke that comes around once in a while — when a player has played for both teams that are competing in the Fall Classic.
There aren’t any defined rules on which players actually get rings from a winning team, but almost always these days, any player who suited up for a team at all throughout the season will get a ring.
So unless the Brewers or Rays did something odd with their ring distribution, Woodford is set either way.
He likely will have a rooting interest of the Rays at the moment, because he’s still technically part of their organization (and he’s from Tampa). But a Brewers win would get Woodford a ring, too.
Jake Woodford’s Season With Brewers, Rays (and Cubs)
Woodford is a 6-foot-4 right-handed relief pitcher who will turn 30 on Oct. 28, before the World Series is over.
He’s originally a first-round pick of the St. Louis Cardinals in the 2015 MLB Draft out of H.B. Plant High School in Tampa, Florida.
Woodford has since played for the Cardinals, the White Sox, the Pirates, the Diamondbacks, the Brewers, the Cubs and the Rays.
He began the 2026 season with the Brewers and had a 6.94 ERA in 16 appearances — ironically, he had signed with the Rays in the offseason but was traded to Milwaukee before Opening Day.
The Brewers released Woodford midway through the season, and the Cubs signed him for a brief stint, in which he had a 9.00 ERA in two outings with Chicago.
Eventually, the Cubs released Woodford, too, and he got one outing with the Rays in September — allowing three runs in 1.1 innings (20.25 ERA).
Woodford will likely reach free agency again in the offseason after being designated for assignment by the Rays, but he still technically belongs to their organization as the World Series is being played.
No Role in World Series
Woodford, of course, would’ve loved to actually pitch in the World Series, but he hasn’t been on any playoff roster for the Rays and his DFA status that Tampa Bay placed on him will keep him from being active in the Fall Classic.
That means Woodford will just watch as his hometown team, which is also his current team sort of, plays in the World Series against the ballclub he pitched 16 games for earlier this year.
Hopefully he’s got room on one of his fingers for a ring.
This Player Gets World Series Ring No Matter if Brewers or Rays Win