Who doesn’t love a good reunion in baseball? It’s always fun to speculate which players could return to a former ball club, and for the Milwaukee Brewers, there are several reunions that could be on the table for the 2026 season.
The Brewers are very particular about who they target in free agency. They are one of the smartest organizations in baseball in terms of identifying and developing talent, and they tend to lean more toward under-the-radar additions on the margins of the roster to address their needs.
The names on this list fit that mold and already have an established familiarity in some form with Milwaukee. From potential minor-league signings to veterans looking for a bounce-back season, here are four names that could return to the organization this offseason.
RHP Peter Strzelecki
The Brewers don’t often — nor do they need to — spend a lot of money on relievers. They are a bullpen factory that seemingly spawns high-caliber relief arms out of nowhere. That said, they value pitching depth as much as any organization in baseball, and they love bringing in low-cost arms that have a ceiling they can dream on.
Peter Strzelecki is just that. He was a member of the Brewers back in 2022 and the first half of 2023 before they traded him to the Arizona Diamondbacks at the trade deadline for Andrew Chafin.
As a rookie back in 2022, Strzelecki threw to a 2.83 ERA with a 2.94 FIP in 35 innings. His numbers dipped in 2023, where he threw to a 4.54 ERA with a 3.79 FIP in 37 innings with Milwaukee before being traded to Arizona. He’s since struggled with performance and dealt with injury after leaving Milwaukee, bouncing around to multiple organizations.
Strzelecki would be a work in progress to get him back to his 2022 form, and he would likely come in on a minor-league deal if acquired. His pitch mix has greatly shifted over the years, reducing the usage of his sweeper while throwing more changeups, cutters, and sinkers, but the shift in pitch usage hasn’t led to better results.
Back in 2022 when he was at his best, Strzelecki’s four-seam fastball, which he threw 53.3% of the time, had an opponent average of .224 with a 29.5% whiff rate. His changeup was also very solid, generating an opponent average of .167 with a 35.7% whiff rate, and his sweeper featured plenty of glove-side movement that paired well with those offerings.
He’s since thrown his sweeper less and his changeup more often. Additionally, Strzelecki has dropped his arm angle two degrees compared to 2022 and has lost both ride and run on his four-seamer.
Establishing a heater he is comfortable with — whether it be getting his four-seamer back to its original form or leaning more into a sinker as a primary– would be step number one in returning to a big-league-caliber arm.
Strzelecki is a malleable arm that has potential with the right help. It’s no coincidence that he was brought in by both the Tampa Bay Rays and Cleveland Guardians, two organizations that are notorious for developing arms just like Milwaukee.
While the results with those two organizations didn’t pan out, he’s worth taking a flier on with a minor-league deal to see if they can recapture his old form.
LHP Jordan Montgomery
Yes, this would technically be a reunion. While Jordan Montgomery never threw a pitch with the Brewers, Milwaukee acquired the southpaw via trade at last year’s deadline and kept him on the roster through the end of the season.
Montgomery, who missed all of 2025 recovering from a torn UCL, reached his peak in 2023 when he won a World Series title with the Texas Rangers and carved through the postseason after throwing to a career-low 3.20 ERA in the regular season. However, things haven’t gone quite his way ever since.
It appeared as if Montgomery was headed for a massive payday that winter, but he ended up signing one-year deal worth $25 for 2024 with a player option in 2025 with the Arizona Diamondbacks. After missing time with injury, Montgomery threw to a dreadful 6.23 ERA in 117 innings with the D-Backs, opted into his player option in 2025, and underwent Tommy John surgery back in March.
Ready to get back on the saddle in search of a bounce back, Montgomery has a profile that would fit well with the Brewers.
His primary fastball is a sinker, and he pairs that with a curveball, changeup, and four-seamer. While Montgomery has hovered around league average in terms of ground-ball rate historically, perhaps leaning into that pitch-to-contact mindset and utilizing his sinker more to take advantage of the defense behind him is a recipe for success. We’ve seen Milwaukee do it with plenty of other arms before.
Coming off an abysmal campaign in 2024 followed by Tommy John in 2025, Montgomery is likely going to settle for a one-year contract and shouldn’t come at a high cost. The Brewers have a need for a southpaw in the rotation (Peralta, Woodruff, Miz, Priester, and Patrick are all right-handers), and he comes with valuable experience pitching on the biggest stage and excelling when the lights were brightest in the World Series.
I am also a firm believer that the Brewers make every move with a purpose. When they acquired Montgomery at the deadline last year knowing he wasn’t going to pitch for them, perhaps they did so with a goal in mind to get him comfortable with the organization.
It was a salary dump for Ariziona, and the Brewers typically aren’t on the other end of that kind of deal. While taking on Montgomery’s salary was a way to reduce the cost of acquiring reliever Shelby Miller, it also gave the Brewers an opportunity to talk strategy with Montgomery, get a gauge for how he fits in the clubhouse, and overall see if he would be a good fit with what this team is trying to accomplish.
The Brewers are very calculated with their moves, and this one in particular felt like there was more behind it than simply taking on Montgomery’s salary. There are already rumors circling that the two parties are in talks of a one-year contract, suggesting that a reunion is very much in the cards.
C Victor Caratini
Victor Caratini had a solid two-year stretch with the Brewers from 2022-2023 and was at one point Corbin Burnes’ unofficial personal catcher. When Caratini came to Milwaukee, Charlie Greene and company completely revitalized his defense behind the dish and turned him into very solid framer and overall defensive catcher.
He’s spent the last two seasons in Houston, where he posted a 113 wRC+ in 2024 and 104 wRC+ in 2025 as the backup to Yanier Diaz. Coming off a year in which he hit .259 with a career-high 12 homers, a return to Milwaukee would make sense at the right price.
Clearly, William Contreras will continue getting the lion’s share of reps at catcher. Moreover, top prospect Jeferson Quero, Just Baseball’s No. 50 overall prospect, is expected to break camp and be the backup to Contreras on the MLB roster.
They will prioritize getting Quero reps if deemed ready, however the Brewers have shown a willingness to carry three catchers in years past, most notably in 2024 with Contreras, Eric Haase, and Gary Sánchez.
While Quero is a strong defensive catcher in his own right, there’s value in bringing in an experienced catcher that is familiar with the staff.
Caratini worked with both Peralta and Woodruff in his time with the Brewers, and having another defensive catcher to help develop young arms like Miziorowski, Priester, Patrick, etc., would go a long way.
At 32 years old, Caratini shouldn’t be expensive, and he would bring more value to the clubhouse than what is in the box score.
C Gary Sánchez
It’s a similar line of thinking with Gary Sánchez, except the Brewers would be bringing him in for his power presence instead of his glove like Caratini.
Sánchez is far from a defensive wizard behind the plate to say the least, but this is a lineup that needs power. But the Brewers don’t have many spots on the roster to address that need for power with so many of their core positions locked up.
That’s where Sánchez would fit nicely as a cost-effective bench option. Injuries have plagued him for the past couple of seasons, so perhaps transitioning to more of a DH role would suit him well and help preserve his health. He could still start once a week at catcher if needed, for example, but he would be there to provide power off the bench when called upon.
Now, Sánchez didn’t exactly tear the cover off the ball in his 89 games with the Brewers back in 2024, hitting .220 with a .699 OPS and 97 wRC+. That said, I don’t think that would stop the Brewers from entertaining the idea of a reunion if the price was reasonable.
Sánchez has hit 10 or more homers in each of his nine seasons from 2016-2024 and was well on pace to clear that benchmark in 2025 had he not spent so much time on the shelf.
In 2025, the Brewers finished with the second-lowest barrel rate in MLB and the lowest in the National League at 6.7%. Sánchez has never finished with a barrel rate below 10% in his entire career.
This past season, the Brewers had the fourth-lowest average exit velocity in baseball at 88.6 mph and the sixth lowest hard-hit rate at 39.3%. Last season, while it was in just 101 plate appearances, Sánchez posted an average exit velocity of 93.3 mph and a hard-hit rate of 57.8%.
It’s also worth mentioning that in his time in Milwaukee in 2024, the Brewers gave him a little bit of run at first base. Perhaps that would be another way they could work his playing time into the lineup if they are intrigued enough with his power.
In all liklihood, the group of position players is set for Milwaukee. But as was mentioned, adding power should be a priority for the front office this offseason, and Sánchez could be one way to address the need in an affordable way.
