As we enter the holiday season, the concept of reuniting with family members and loved ones is on the mind. While there may be a few people we’re a little less than thrilled about sharing a table with (maybe it’s that know-it-all cousin of yours you never really got along with?), there will also be some folks we haven’t seen for quite some time who will fill our evenings with joy and laughter. We’ll realize, in that moment, just what we’ve been missing. Right then, even if for a short time, we are whole again.

It’s in this vein that the Chicago Cubs will be looking fill out their 2026 roster, and a “family reunion” of some sorts may just be what the doctor ordered. There are a handful of heroes of past Cubs rosters who are looking for homes next year, and it may be that they choose the familiar home they once had instead of a brand-new city in which to settle down. I’ll examine three candidates: designated hitter Kyle Schwarber, and relief pitchers Mark Leiter Jr. and Andrew Chafin. Together, we can endeavor to decide just how likely it is for them to sit down at the Cubs’ dinner table for the foreseeable future. 

Reunion Candidate #1: Designated Hitter Kyle Schwarber
Kyle Schwarber was one of the more beloved Cubs hitters during his time in Chicago. From hitting a ball atop the right-field scoreboard in the 2015 NLDS to heroically returning for the 2016 World Series (after missing the lion’s share of the season due to an unfortunate knee injury), the left-handed hitter made his mark in Chicago. His time was cut short when the team decided to non-tender him, ultimately spending the same money on Joc Pederson instead ahead of the 2021 season. Now, the Cubs will have a chance to rectify that error by bringing Schwarber home. 

Since 2021, the left-handed DH has been among the best in baseball, averaging a 135 wRC+ for the Nationals, Red Sox, and Phillies. Once a strict platoon bat, Schwarber even has some some mojo against left-handed pitchers, finishing with a 162 wRC+ against them in 2025. He’s strictly a DH, but his bat is so good that it doesn’t really hold him back from being useful.

Why Schwarber might fit into the Cubs’ plans:
The Cubs are slated to lose (arguably) their best hitter to free agency, in Kyle Tucker. The team could swing their incumbent at DH, Seiya Suzuki, back to right field for the 2026 season, which would open up a perfect spot for Schwarber. His left-handed bat was actually better than Tucker’s was last year, and he would add significant thump to the lineup.

Why Schwarber might not fit into the Cubs’ plans:
The Cubs just don’t put a massive emphasis on DH most years. They value positional flexibility, and Schwarber offers none of that—though he might be capable of moonlighting a little at first base. As well, they have two rookies in Owen Caissie and Moisés Ballesteros, who both hit from the left side. Either could conceivably slip into the position. 

How likely is a reunion? About as likely as that one uncle of yours not getting political this week at the dinner table.
There are already rumors that the Philadelphia Phillies are going to try to keep him (and they aren’t afraid to jump a market). According to ESPN insider Jeff Passan, the market is hot for the DH. Could the Cubs decide that Schwarber, who probably won’t need a seven-year commitment, is the player they should get irrational about? Perhaps, but it feels like another team will decide to do that instead. As fun as it would be, it seems like a reunion here is unlikely. 

Reunion Candidate #2: Reliver Mark Leiter Jr.
Leiter spent two and a half seasons in the Windy City after the Cubs helped to revive the then-31-year-old’s career. He hadn’t pitched an inning in the majors since 2018, but by the middle of 2022, he had established himself a key cog in the Cubs’ bullpen. Flashing a plus splitter that was devastating to left-handed hitters, the reliever had finally found a home—that is, until the trade deadline of the 2024 season.

With the Cubs staring at decision point (choosing between making a run for it and selling off some assets for the future), the New York Yankees made an offer for the right-hander pitcher that the Cubs couldn’t turn down. The Cubs acquired young reliever Jack Neely and infielder Ben Cowles, and Leiter was sent to the city that never sleeps. While Leiter was pretty good in New York, the Yankees made the decision to non-tender the 34-year-old last week. making him a free agent.

Why he might fit into the Cubs’ plans:
The Cubs bullpen is currently wide open and quite unsettled. Returning closer Daniel Palencia will be coupled with recently-signed Phil Maton, but there is little clarity regarding the rest of the bullpen. One area in which the Cubs are lacking; anyone who specializes, specifically, in getting left-handed hitters out. Despite being right-handed, Leiter uses his splitter effectively against opposite-handed hitters, finishing with a 2.61 xFIP against lefties last season.

Why he might not fit into the Cubs’ plans:
While the Cubs are looking to rebuild their bullpen, they may aim higher than Leiter. Though he’d offer the comfort of familiarity, Leiter really struggled against right-handed-hitters, posting significantly worse numbers against them; a strikeout rate of just 12.1% and an xFIP well over 5.00. If there’s enough concern that he’s too specialized, the Cubs may not see a place for him in their revamped 2026 bullpen.

How likely is a reunion? As likely as I am to pull a hamstring during the Turkey Trot: 50/50.
The Cubs need a lot of relievers this offseason, and you’d have to imagine that if there’s an organization out there who believes they can get the most out of Leiter, it’s the Cubs. With all of their left-handed specialists leaving, it makes Leiter that much more attractive. So while I wouldn’t gamble my hard-earned money on it, I think there’s a good chance this one could happen; much like a white Christmas remains possible, 

Reunion Candidate #3: Reliever, Andrew Chafin
Chafin feels like he was part of the Chicago Cubs for longer than he was, but the left-handed reliever only spent some inactive time in 2020 and half of the 2021 season with the team. Admittedly, it was a great 31-game sample, as the left-handed pitcher put up a 2.06 ERA and 0.9 fWAR (which is a lot for a partial season!), ultimately earning a trade to Oakland that would bring back Triple-A outfielder Greg Deichmann and a minor leaguer with an electric arm—Daniel Palencia.

Since 2021, Chafin has been signing for playoff non-contenders and then being traded at the deadline to a playoff hopeful. Now 35 years old, the reliever is once again looking for a new home. 

Why he might fit into the Cubs’ plans:
As I detailed with Leiter, the Chicago Cubs’ bullpen is currently empty. They’ve lost most of their bullpen, which also includes the non-tender of depth piece Eli Morgan. The team will need a lot of relievers, and Chafin could fit back in as a left-handed option, The Cubs have not shied away from older lefties; their primary options just a year ago were the 37-year-old Drew Pomeranz and 38-year-old Caleb Thielbar. Comparatively, Andrew Chafin represents a youth movement.

Why he might not fit into the Cubs’ plans:
On the surface, he looks like he might be done as a big-league pitcher. Chafin’s fastball has declined to the wrong side of 90 mph, so while his ERA remained sterling (2.41), his xFIP climbed to nearly 4.00 last year. His strikeout rate dropped by 3%, and his walk rate ballooned to 13.3%. The Cubs already have a lack of velocity in their pen, so adding another soft-tosser may not be the best gamble to take.

chart (11).png

How likely is a reunion? About as likely as I am to eat a second slice of apple pie on Thursday
On the surface it may seem like a good idea (my eyes being larger than my stomach), but once I think about it, it probably isn’t so, at my age. Chafin has a lot of signs of decline, and I’m not sure that the Cubs will be in a place to see if he still has it. Maybe they see something within his biomechanics and think they can squeeze and find 2 mph on his fastball again, but I think it’s more likely (as he hits the back end) of his 30’s that he’s trending toward the end. 

What do you think of these reunion candidates? Do you have a favorite one? Maybe there’s a reunion out there that I didn’t think of? Let us know in the comment section below!