The Philadelphia Phillies may not be playing in the 2026 World Series, but their fingerprints are on both bullpens.
As the Tampa Bay Rays and Milwaukee Brewers prepare to face off in the Fall Classic, two former Phillies teammates find themselves on opposite sides of baseball's biggest stage.
Here's how each found their way to the World Series.
It was September 17, 2020. The Phillies, under the eyes of manager Joe Girardi, were working their way towards the end of a 60-game COVID-shortened campaign. Just as much as that year is a memory many of us want to forget, Garrett Cleavinger likely felt much the same.
At the time, the 26-year-old left-handed reliever was making his way up through the Phillies organization. He was one of the select group of players the Phillies had as their alternate roster pool. Now a part of the active roster for a second time, Cleavinger trotted out of the bullpen to make his major league debut against the New York Mets in front of an empty Citizens Bank Park.
Having just watched his teammate Brandon Workman give up the lead, Cleavinger entered to face Robinson Canó with one runner on and one out as the Phillies were down 8-6 in the top of the ninth. Canó welcomed Cleavinger to the major leagues with a two-run home run to settle what would be a 10-6 loss for the Phillies.
Cleavinger was optioned down to the alternate training site the next day.
Three months later, Cleavinger became a part of a three-team trade, going to the Dodgers as the Phillies acquired Josè Alvarado from the Rays.
Fast-forward to today and Cleavinger returns to the active roster for the Rays after being left off the roster for the ALCS against the Guardians. The reliever had missed much of September dealing with left forearm tightness, though he returned in time for the ALDS.
Now back on the roster, Cleavinger will be in the mix in the rotation, owning a 4.79 ERA on the season.
Watching as Cleavinger made his MLB debut was another left-handed reliever who made his debut with the Phillies just a month before: Jojo Romero.
In an interview with John Denton a few years later, Romero described how the nerves were getting to him as he prepared to make his debut. The Phillies were down 11-2 against the Atlanta Braves and Romero could not even hit the catcher due to his nerves in the bullpen. Then came a moment that would live in infamy in Phillies lore.
“After that I had a Red Bull to kind of fire myself up before going in and I just [smashed the can on his arm] and didn’t think anything of it,” Romero said to Denton. “But then, when I struck out the side, my teammates told me, ‘You know, you’ve got to do that every time now, right?’ So, it carried on from there.”
Romero does not smash Red Bull cans ritualistically anymore, but the reliever has gone on to have a smashing major league career. In 2022, Romero was traded to the Cardinals for Edmundo Sosa. At the time, the reliever owned a 7.89 ERA. Five years later, Romero was a consistently strong reliever for the Cardinals with a 3.07 ERA with the Cards.
At the Trade Deadline this year, Romero found himself, along with Dustin May, getting traded to reinforce the Brewers. Now, he is one of the most-trusted pieces in the Brewers’ bullpen.
In Game 4 of the NLCS, Romero pitched two shutout innings in middle relief, striking out Shohei Ohtani, Freddie Freeman, and Max Muncy.
While the pair of left-handed relievers are the only active former-Phillies in the World Series, there is a third player whom the Phillies drafted once upon a time.
Yet another left-handed reliever, Shane Drohan was drafted by the Phillies in the 23rd round of the 2017 MLB Draft out of high school. The pitcher opted to go to college instead, pitching for Florida State until the Red Sox drafted him in the fifth round in 2020.
Now, the rookie reliever is in the Brewers’ bullpen, where he will await his chance to contribute on the biggest stage in baseball.
Regardless the outcome, at least one player connected to the Phillies’ organization will end the season as a World Champion.
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