The Minnesota Twins have a rotation question that extends beyond choosing five starters for Opening Day. Joe Ryan, Pablo Lopez, Dean Kremer, and Bailey Ober could all reach free agency after 2027 under their current contract timelines.
That shared clock requires different decisions. The Twins should rank the four by retention priority, weighing health, expected contribution and the cost of replacing their innings. Keeping every available starter this winter could provide depth without resolving what comes next.
Twins On SI's front-office outlook identified that approaching turnover as a major organizational challenge. The next step should be a plan for each pitcher, with Ryan leading the extension conversations and more conditional approaches elsewhere.
Ryan and Kremer Should Lead the Retention List
Ryan should rank first. He finished 2026 with a 3.79 ERA and 159 strikeouts in 144.2 innings, offering established production that Minnesota would otherwise need to replace.
His $13 million mutual option also needs context. As the Twins' contract tracker explained, declining it would leave him under arbitration control for 2027. An option decision would not automatically make him a free agent.
The Twins should explore a deal that purchases additional years beyond that remaining control. They also should establish a price limit before talks begin. Retaining Ryan for another campaign could still have value if an extension proved too expensive.
Kremer belongs second on the retention list, with a shorter commitment as the preferred approach. After arriving from the Baltimore Orioles, he recorded a 3.48 ERA across 10 starts and 54.1 innings for Minnesota. His full-year ERA was 4.68, so the encouraging finish should remain part of a larger evaluation.
A modest extension could preserve useful innings while younger starters develop. Minnesota should compare that cost with available alternatives before making a multiyear promise.
Lopez and Ober Require More Conditional Plans
Lopez should rank third for an immediate extension discussion because his recovery complicates the timing. His existing deal runs through 2027, and his return from Tommy John surgery remains central to the rotation's outlook. MLB's October assessment outlined the uncertainty surrounding his effectiveness upon returning.
The Twins should evaluate his rehabilitation progress before adding substantial guaranteed years. Waiting for more medical and pitching information could produce a better decision, even if it leaves his longer-term status unresolved entering camp.
Ober would rank fourth. Minnesota should explore his trade market while determining whether he projects as a regular starter in its preferred rotation. A clear evaluation matters more than allowing his remaining control to expire without a plan.
The club also needs enough depth to handle a delayed recovery or an injury elsewhere. Trading Ober would make sense only if the return and the remaining pitching justified the move.
Taj Bradley, Connor Prielipp and Zebby Matthews give Minnesota younger choices, but their presence should inform the veteran decisions individually. The Twins should aim to secure at least one established starter beyond 2027 while preserving room for those pitchers to develop.
Four approaching contract deadlines do not require four departures. They require a retention order, a price for each commitment, and a realistic replacement plan.
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