The Five Funniest Old Friend Reunions the Twins Could Make This Deadline

Dozens of players are traded every deadline. Fans love some and hate others. Fans also beg for their favorite players to come back. Admit it, you want them to trade for Luis Arraez, Sonny Gray, Louis Varland, and, if you're a real sicko, Tyler Wells. But for Twins fans, what would be the funniest possible Welcome Home trade candidates? Here's my top five.

5. Randy Dobnak, SP (KC)
Randy Dobnak went from beloved folk hero to unwitting villain faster than any player I have ever seen because he had the temerity to commit two unforgivable sins. First, he was the last man standing in 2019 as the club's third-best starter after injury, ineffectiveness, and a lack of reinforcements sapped the Twins of all their starting depth. Second, he had the gall to sign a very modest contract that paid him nine million dollars over five years before getting injured. Twins fans have never forgiven him for that.

He's a great story, perhaps bordering on a sideshow, a husky sinkerballer with a horseshoe mustache and a winning smile who was signed out of independent baseball and drove Uber in the offseason. After years marred by injury and ineffectiveness, Dobnak left the Twins organization not as an MLB rotation piece but as perhaps the most beloved St. Paul Saint of the Triple-A era.

Why would the Twins trade for Dobnak? They've shown a penchant for using bulk relievers this season, and they might need a little more rotation depth even after acquiring Dean Kremer. And Dobnak has thrown 26 innings to the tune of a 1.04 ERA for the Kansas City Royals, including seven shutout innings against the Twins last week.

4. Isiah Kiner-Falefa, UT (BOS)
Isiah Kiner-Falefa had perhaps the shortest tenure as a Minnesota Twin in the modern era, as it didn't even last 24 hours. He was acquired in the 2022 offseason for Mitch Garver, alongside Ronny Henriquez. The following day, he was packaged with Josh Donaldson and Ben Rortvedt and sent to the Yankees for Gary Sánchez and Gio Urshela.

The Twins have trotted out several utility infielders to play shortstop for them this season, so what's one more? It's not like Kaelen Culpepper is beating down the doors. It's still early, anyway. They still have time to trade for him and then hours later send him somewhere else.

3. Brent Headrick, RP & Luis Gil, SP (NYY) - Specifically in return for Ryan Jeffers
There's a lot going on with this one, but hear me out. Brent Headrick was a DFA casualty in 2025 (when the Twins bullpen was good), snatched away by the Yankees in February of 2025. He's put up a 1.84 ERA across 78 innings out of New York's bullpen and would have been a very good addition for the Twins—if they didn't already have four lefties in their bullpen after trading for A.J. Minter.

Luis Gil was traded to the Yankees ahead of the 2018 season for Jake Cave. Gil was 19 at the time (a year older than Jhomnardo Reyes, who was just traded for Kremer, much to the chagrin of many fans), but he was excellent for the Yankees between 2024 and 2025, starting 40 games with a 3.45 ERA and winning Rookie of the Year in 2024. He's a great example of why self-scouting is so important, though he's struggled this season and is currently on the injured list.

Were the Twins to trade Jeffers for this package, not too dissimilar to the Anthony Volpe-Camilo Doval (two Yankees who have been spiraling lately) package that circulated the baseball world last week, basically everyone would be mad. The anti-Jeffers-trade crew would be upset he was traded. The pro-Jeffers-trade crew would be upset at the return. The people who have never forgiven the Twins for trading away Gil would say it's too little too late.

2. Tyler Mahle, SP (SF)
Tyler Mahle was the headliner for the Twins' most significant trade deadline during the Derek Falvey era. The Twins sent Spencer Steer, Christian Encarnacion-Strand, and Steve Hajjar to Cincinnati for his services at the 2022 deadline for the last year and a half of Mahle's contract. They received nine starts for this investment, as Mahle was lost for the season twice in two years. He was solid when healthy (and to hear him tell it, he always was), but he just wasn't healthy. And Steer had a great start in Cincinnati, further frustrating Twins fans.

Mahle continued to struggle with injury since leaving the Twins, but he had a 2.82 ERA in 16 starts with Texas last season, and since returning from a hamstring injury this season, he's got a 3.06 ERA in six starts. The Twins already made a trade for a backend starter in Kremer, but if they decided to shift some more assets around or bolster their rotation a bit more, Mahle could be a solution. As long as they don't Google "Tyler Mahle hamstring injury," anyway.

"Oh but Gregg, you buffoon, the Braves just made a trade for Mahle last night!" I hear you say. Well, starting pitchers can be traded twice during a single deadline. Maybe the Braves will get cold feet. Ever heard of Jaime García??

1. Emilio Pagán , RP (CIN)
Emilio Pagán's 2022 is up there with the worst seasons for a reliever in Twins history. Not necessarily because he was the worst reliever, but because he had a penchant for giving up bombs at the most inopportune times: in the bottom of the ninth, against Cleveland, and in a pennant race. His meltdowns did put the Twins in position to draft Walker Jenkins, and he was actually pretty good in middle relief for the division-winning 2023 Twins, but Minnesotans never forget a slight.

Pagán signed a two-year deal with Cincinnati ahead of the 2024 season and was a pretty effective closer for them in 2025, netting him another contract worth $10 million in 2026 with a player option for another $10 million in 2027. He's struggled this season and missed some time due to injury, but he had a 1.93 ERA in July and pitched himself back into the closer role just in time for the Reds to shop him.

If you removed the Twins history component, he'd probably be on some lists for good fits with the Twins, as a low-end overpaid closer is a nice slot for the Twins who want to improve the pen without giving up much in the way of prospects. And if you haven't heard, Dan Hayes and Ken Rosenthal at The Athletic threw out Pagán's name as an option for the Twins.

Honorable Mentions: Spencer Steer. Steven Okert, Michael Tonkin (as a signing, only to be waived August 10th), Dallas Keuchel, Trevor Richards, Daniel Susac

View our top trade candidates list, up to nearly 70 names and updated regularly!