Which Young Twins Should Get an Extension This Winter?

Major League Baseball has increasingly become a league where teams are willing to bet on young players before the players have had much opportunity to cash in on their potential.

That trend has accelerated in recent years. Teams have handed out long-term contracts to players with very little service time, and some have even made commitments before a player reaches the majors. In 2026 alone, Colt Emerson, Cooper Pratt and Luis Lara signed extensions before making their MLB debuts, while several other highly regarded young players received significant guarantees almost immediately after reaching the majors.

The strategy is relatively simple. A team gives a young player financial security early, while potentially buying out arbitration seasons and some free-agent years at a lower cost than the player might command after establishing himself as a star.

The Minnesota Twins have watched that trend from the outside. This winter, they could finally decide to participate. General manager Jeremy Zoll said the organization plans to explore contract extensions with some of its young players during the offseason. Zoll also explained why he prefers to have those discussions away from the regular season.

“As it pertains to extension conversations, that’s definitely something we’re going to explore this offseason and going forward,” said Zoll. “I know there have been in-season extensions around the league. Personally, I don’t think it serves anyone particularly well to potentially create a distraction for players during the season on those fronts. So those will be things we’ll engage in this offseason and we’ll see how that all shakes out.”

That leaves a fascinating question for the Twins. Who exactly should they be talking to?

The Twins Have Seen Both Sides of This Equation

There is an obvious appeal to getting ahead of the market. If a player becomes a star, the price is going to increase dramatically. If the Twins can identify that player early enough, they could potentially secure several years of production at a manageable cost.

But the organization also has plenty of evidence for why patience can be valuable. As explored earlier this year, the Twins had opportunities to make long-term commitments to players such as Royce Lewis, Jose Miranda and Matt Wallner when their perceived values were significantly higher.

Lewis looked like an obvious extension candidate following his spectacular 2023 campaign. He hit .309/.372/.548 with 15 home runs and a 149 OPS+ in 58 games before starring in the postseason. Today, Lewis is coming off a disappointing 2026 season in which he hit .227/.287/.380 with a 86 OPS+ and 0.9 WAR.

Miranda provides another cautionary tale. After posting a 114 OPS+ as a rookie in 2022, his production collapsed in 2023 (55 OPS+) before rebounding in 2024 (112 OPS+). There were flashes of his strong bat-to-ball skills, but he never put it all together at the big-league level. He was eventually out of the organization and played the entire season in the minors this year. 

Wallner provides another example of the uncertainty surrounding young players. His power looked like something the Twins could build around, but injuries and strikeouts have prevented him from establishing himself as a consistent everyday player. In 2026, he hit just .167/.259/.292 with a 55 OPS+ in 34 games before being demoted to Triple-A for the remainder of the season. 

The lesson isn't that extensions are bad. It is that the Twins need to be extremely selective about which players receive them. That brings us to this winter's potential candidates.

Taj Bradley

The case for an extension: Bradley might have the strongest argument among Minnesota's young pitchers. The 25-year-old right-hander made 31 starts and threw 178 1/3 innings in 2026, posting a 3.73 ERA, 3.82 FIP and 205 strikeouts. He produced 4.4 WAR while becoming one of the most important pieces of Minnesota's rotation. There is also a reason to believe the best is still ahead as he is only 25-years old. Bradley has already demonstrated the ability to miss bats while carrying a starter's workload, and he has three years remaining before free agency.

The case against an extension: Pitching is inherently risky, particularly when discussing a multi-year commitment. Bradley has only one season at this level of workload and production. His 1.22 WHIP and 76 walks also show there is still room for improvement. The Twins would be buying into both his 2026 breakout and the expectation that he can sustain it.

Luke Keaschall

The case for an extension: Keaschall looks like exactly the type of player teams target with early extensions because he is under team control through 2031. At 23, he followed his impressive 2025 debut with a full 2026 season in which he hit .282/.374/.407 with 10 home runs, 20 stolen bases and 2.2 WAR. His 120 OPS+ shows his offensive production was comfortably above league average.  More importantly, Keaschall's game isn't dependent on one tool. He provides on-base ability, speed while still having room to develop more power. The Twins can plug him into the top of the lineup for the foreseeable future. 

The case against an extension: His power profile is still somewhat uncertain. Ten home runs in 620 plate appearances isn't overwhelming, and his .407 slugging percentage leaves some questions about his long-term offensive upside. His defensive metrics also weren't particularly strong across his various positions in 2026. An extension would be betting that Keaschall's overall offensive profile continues to develop.

Walker Jenkins

The case for an extension: Jenkins may have the highest offensive ceiling of anyone on this list. The fifth overall pick in 2023 entered 2026 as one of baseball's top prospects and ultimately reached the majors at age 21. Before his promotion, Jenkins produced a .323/.417/.559 line with 14 home runs, 17 stolen bases and a 151 wRC+ across 73 minor-league games.

His major-league debut was much more modest, as he hit .226/.293/.393 with a 91 OPS+ in 93 plate appearances. But that small sample doesn't erase the larger body of work. Jenkins remains one of the organization's most intriguing long-term building blocks.

The case against an extension: This is precisely where the Lewis lesson comes into play. Jenkins has barely begun his major-league career. The Twins would be committing significant money based primarily on prospect pedigree and minor-league performance rather than established MLB production.

There is also the Scott Boras factor. Jenkins' representation could make an early deal more difficult to negotiate, particularly if the player believes his eventual earning power could be enormous.

Connor Prielipp

The case for an extension: Prielipp's underlying numbers provide more optimism than his ERA. The left-hander finished 2026 with a 4.87 ERA but a 3.73 FIP over 125 2/3 innings. He struck out 128 hitters while allowing only 14 home runs. Considering his lengthy injury history, simply completing a full season while establishing himself as a major-league starter represents an important step forward. If the Twins believe his FIP is more representative of his future performance, there could be an opportunity to buy low before his results catch up with his underlying skills.

The case against an extension: This is a much larger projection than Bradley. Prielipp still hasn't demonstrated sustained major-league success, and his 1.29 WHIP and 4.87 ERA leave plenty of uncertainty. He also has a history of significant injuries, which makes a long-term pitching commitment particularly complicated. There is a reasonable argument for simply letting Prielipp prove more before committing.

Kaelen Culpepper

The case for an extension: Culpepper's 2026 season provided two encouraging data points. First, he dominated Triple-A, hitting .271/.367/.478 with 14 home runs and 17 stolen bases in 74 games. Then he reached Minnesota and held his own, hitting .274/.328/.393 with a 102 OPS+ over 33 games. The combination of shortstop defense, athleticism and offensive upside makes Culpepper an intriguing long-term piece.

The case against an extension: He has only 128 major-league plate appearances. That's not enough information to know whether his offensive production will translate over a full season. His 28 strikeouts against just six walks in 128 plate appearances also highlight areas that need improvement. Culpepper may be a player the Twins should monitor closely rather than rush to sign.

Emmanuel Rodriguez

The case for an extension: Rodriguez remains one of the organization's highest-upside offensive players. He reached the majors in September after another productive minor-league season (140 wRC+) and made his debut at 23. His combination of power, plate discipline and athleticism has made him one of the more intriguing prospects in the system for several years. The Twins would be buying before Rodriguez has had a chance to establish himself as a major-league hitter. That's exactly what makes an early extension potentially valuable.

The case against an extension: There simply isn't enough MLB evidence yet. Rodriguez went 8-for-45 with two home runs and a .178/.229/.400 line during his brief major-league debut. That obviously isn't enough to make a judgment about his future, but it demonstrates how much uncertainty remains. There are also questions about whether his long-term defensive home will maximize his value. The offensive upside is exciting, but the Twins would be paying for potential.

Where Should the Twins Start?

There is no reason for Minnesota to hand out extensions simply because other teams are doing it. The purpose of an early extension is to identify a player before the market catches up and create cost certainty before arbitration and free agency become expensive. But the Lewis, Wallner, and Miranda examples demonstrate how quickly that calculation can change.

Bradley has the strongest major-league track record of this group. Keaschall has the largest body of MLB work among the position players. Jenkins has perhaps the greatest long-term ceiling. Prielipp represents an intriguing buy-low opportunity, while Culpepper and Rodriguez remain higher-risk bets on potential.

The Twins don't need to pick just one. But they also don't need to force the issue with all six. Zoll has made it clear that extensions will be part of the offseason conversation. Now the difficult part begins: deciding which young players have shown enough to justify turning potential future value into guaranteed money today.

For a franchise trying to build its next competitive window, those decisions could be among the most important of the winter.

What player or players should the Twins approach for contract extensions this winter? Leave a comment and start the discussion.

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