16 former Cubs who will have a chance to win the 2025 World Series

The 2025 MLB playoffs are at hand and, for the first time since 2020, the Chicago Cubs are in on the fun, hosting a best-of-three NL Wild Card Series at Wrigley Field this week.

You won't have to tune in exclusively to that game to see familiar faces, though. More than a dozen former Cubs can be found on other postseason-bound rosters in both the American and National League. There are some big names, sure, but a number of players you've probably forgotten about since they called Chicago home.

These 16 former Cubs are playing in the 2025 MLB playoffs

Kyle Schwarber, Nick Castellanos and David Robertson lead the Phillies

Likely NL MVP finalist Kyle Schwarber is looking to lead the Philadelphia Phillies to a World Series for the first time since 2022 - and to a title for the first time since 2008. On the heels of a monster 56-homer and 132 RBI campaign, the free-agent-to-be is ready to add to an already impressive October resume.

Another former Cubs slugger could be in his final days with Philadelphia in Nick Castellanos. Tensions have been high over his diminished role this season, and there's rampant speculation the Phillies could look to move him this winter. Last, but certainly not least, veteran reliever David Robertson, who joined the team late this summer, is looking to bring home a ring with one last go-round at age 40.

A Cubs Cy Young finalist and bullpen castoffs in the National League

Elsewhere in the National League field, we find the #1 overall seed Milwaukee Brewers and the aforementioned Padres. San Diego boasts one of the most impressive bullpens in the game - and one of its biggest contributors is former Cubs right-hander Jeremiah Estrada, the not-so-proud owner of a 5.51 ERA in 17 appearances with Chicago from 2022-23.

Since joining the Friars, though, he's been a completely different pitcher. Estrada owns a 3.22 ERA over the last two seasons, while averaging nearly 14 strikeouts per nine. That hurts.

Estrada is joined by a former Cubs NL Cy Young finalist in Yu Darvish, who could end up drawing a start in the Wild Card Series against his former club. The 39-year-old has seen his stuff drastically diminish, but he can still get outs through his wide-ranging arsenal and ability to spin just about every one of his pitches.

Should the Cubs get past San Diego, they'll square off against the Brewers in the NLDS - and Milwaukee relievers Trevor Megill and Rob Zastryzny could both play a part in that series. Megill just returned from the IL, giving a huge boost to the Brewers' bullpen, and Zastryzny, who won a World Series ring with the Cubs as a rookie in 2016, has been sharp in limited action, as well.

Cody Bellinger, Aroldis Chapman highlight list of former Cubs playing on AL playoff teams

On the American League side of the bracket, the Boston Red Sox and New York Yankees square off in one of the Wild Card matchups - pitting a pair of former Cubs against one another. Aroldis Chapman, who was acquired by the Cubs at the 2016 trade deadline, is now closing for Boston - giving him the chance to slam the door against the team he spent most of his career with, the Yankees.

Meanwhile, Cody Bellinger is looking to bring championship baseball back to the Bronx. After the Cubs dumped his salary in a trade last offseason, Belli turned in a 5.0 bWAR season for New York - his highest single-season mark since his 2019 MVP campaign.

They aren't the only former Cubs in that playoff series, though. Thirty-seven-year-old left-hander Justin Wilson is a piece of Alex Cora's Red Sox bullpen - he was part of the last Cubs playoff team (excluding 2020) back in 2018 and was a go-to arm for manager Joe Maddon, making 94 appearances in his year-and-a-half on the North Side.

Mark Leiter Jr. hasn't been able to replicate the success he had with the Cubs since being traded to New York last year, with an ERA pushing 5.00 this year, but he's gotten regular opportunities out of the Yankees' pen, as well.

Javier Baez - and a hodge-podge of former role players and bullpen arms

The Detroit Tigers limped into the playoff picture - and Cubs fans can't talk about that team without mentioning Javier Baez. A resurgent first half netted El Mago an All-Star selection, but his production cratered out down the stretch, with his OPS finishing down over 200 points in the second half.

Still, he's fun to watch and still capable of impacting the game on both sides of the ball. More surprising might be the fact he was outshined by another former Cubs infielder on the team, Zach McKinstry, who was also an All-Star this year.

He was nearly a 3.0 bWAR player for Detroit this year, finishing the year with a 113 OPS+ that trumps the minuscule 75 OPS+ he put up as a member of the Cubs in 47 games back in 2022. Another case of a change of scenery paying off in a big way.

Castoff infielder finding success in a new home? If that's your cup of tea but you're not all-in on McKinstry, Miles Mastrobuoni is thriving for the AL West champion Seattle Mariners, with his .620 OPS checking in 150 points above what he produced for the Cubs in 2024. OK, maybe thriving is too strong of a word, but he's definitely put up better numbers with the M's than he did with the Cubs.

Rounding out this list? A pair of Blue Jays pitchers: Tommy Nance, who pitched for the Cubs back in 2021 (7.22 ERA in 28 2/3 innings) and Brendon Little, who made one appearance (his MLB debut) with Chicago in 2022. The long and short of it all? You're going to see a lot of familiar faces as the MLB playoffs get underway this week. Hopefully, none of them come back to haunt the Chicago Cubs.