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The Minnesota Twins have several important decisions to make this offseason, and their starting rotation will be near the top of the list. Joe Ryan and Bailey Ober are both approaching free agency after the 2027 season, making them potential trade candidates as the organization considers its long-term direction.
Ryan is the more obvious trade candidate. He has established himself as a frontline starter, and contending teams have pursued him in the past. Ober's future is less certain after two consecutive disappointing seasons and a significant decline in velocity. Some fans will argue the Twins should move on from the right-hander before his performance declines further.
However, these decisions are connected. If the Twins trade Ryan, they should be much more inclined to keep Ober. Minnesota cannot afford to remove multiple established starters from its rotation without creating additional questions about its pitching depth.
Starting Pitching Depth Is Never Enough
The Twins entered 2026 with plenty of starting pitching options. That depth quickly became a necessity rather than a luxury. Pablo López suffered a season-ending elbow injury during spring training, while David Festa experienced a shoulder setback that delayed his availability. Mick Abel also landed on the injured list with elbow inflammation early in the season. Those injuries tested Minnesota's rotation before the team could establish any consistency.
The club eventually added arms and shuffled its options to get through the season. Even with a sizable group of starters, injuries and performance issues made the rotation a constant work in progress.
Minnesota should remember those lessons when evaluating its 2027 roster. López is expected to return, and the organization has several younger options who could earn rotation spots. Taj Bradley, Zebby Matthews, Connor Prielipp and Abel give the Twins reasons to feel optimistic about their pitching future.
Still, young pitchers come with uncertainty. Some will take important steps forward, while others might need additional development time or experience setbacks of their own. Counting on every potential starter to remain healthy and productive is not a realistic roster-building strategy.
If the Twins trade Ryan, keeping Ober would provide another experienced option who knows how to navigate a major league rotation. Removing both veterans could leave Minnesota relying heavily on young pitchers and internal improvement.
Bailey Ober's Declining Velocity Raises Questions
Ober's recent performance has created legitimate questions about his future in Minnesota. After posting a 5.10 ERA in 2025, he finished the 2026 season with a 4.47 ERA across 131 innings. He posted a 17.1 K%, a concerning decline (down 26.9% in 2024) for a pitcher who previously demonstrated an ability to miss bats.
The most significant concern is his fastball velocity. Ober averaged approximately 88 mph with his fastball in 2026, a substantial drop from the 91.7 mph he averaged in 2024. His command and ability to change speeds have helped him succeed throughout his career, but there is less room for mistakes when hitters can attack his fastball.
Ober is projected to earn $6.9 million in arbitration for 2027. That is a considerable commitment for a pitcher coming off a season with diminished results, particularly for a team trying to allocate resources toward several roster needs.
However, the situation is not quite as simple as looking at his ERA and velocity. FanGraphs' dollar valuation placed Ober's 2026 contribution at approximately $10.2 million. That suggests he still provided value beyond his salary, even if his performance fell short of expectations.
The Twins must decide whether Ober can regain enough velocity and effectiveness to justify another season. They also need to consider what it would cost to replace his innings. Non-tendering or trading him might create an opening for a younger arm, but it would also remove an experienced starter from the depth chart.
Joe Ryan Remains a Valuable Trade Chip
Ryan has spent multiple seasons appearing in trade rumors, and the speculation is unlikely to disappear this winter. Contending teams pursued him before the 2025 trade deadline, with the Boston Red Sox among the clubs reportedly involved in discussions. Minnesota ultimately kept him, but his approaching free agency creates another opportunity to consider a deal.
His 2026 campaign was a tale of two halves. Ryan made his second consecutive All-Star team after posting a 2.86 ERA with 128 strikeouts across 110 1/3 innings before the All-Star break. He looked like the kind of frontline starter who could attract a substantial return from a team pursuing a championship.
The second half was far more difficult. Ryan struggled after the break, allowed six home runs in a July outing against Cleveland, and subsequently landed on the injured list with a left glute strain. He finished the season with a 3.79 ERA, 159 strikeouts and 144 2/3 innings across 27 starts. Those numbers still make Ryan an attractive trade candidate. He has demonstrated that he can perform at an All-Star level, and teams seeking reliable postseason rotation help will have reasons to inquire about his availability.
Ryan is projected to earn $9.6 million for 2027, adding another layer to Minnesota's decision. The Twins could retain him for one more season and attempt to compete, or they could explore whether another organization would offer the kind of return that improves their long-term outlook.
Trading Ryan would not automatically mean Minnesota is giving up on 2027. A strong return could address other roster weaknesses and provide players who contribute immediately. But the Twins would need to account for the innings and production they would be losing.
The Twins Need to Consider Both Decisions Together
The Twins should evaluate their starting rotation as a complete unit rather than treating each veteran's future as an independent decision. Ober might be the easier player to move on from based on his declining velocity and recent performance. Ryan, meanwhile, could generate a stronger trade return because of his higher ceiling and established track record. But the consequences of trading either pitcher change depending on what Minnesota does with the other.
If the Twins trade Ryan, retaining Ober becomes much more appealing. Minnesota would already be losing an All-Star-caliber starter, and creating another opening would place additional pressure on its younger options. Ober's experience and potential to rebound could be particularly valuable in that situation.
If Ryan remains in Minnesota, the Twins could have more flexibility to explore an Ober trade or non-tendering him. Even then, they should be careful not to underestimate the value of having several capable starting pitchers available.
The Twins have an opportunity to reshape their roster this winter, but they should not confuse trading from a position of strength with weakening that strength too much. Ryan and Ober are intertwined because the outcome of one decision will influence the other. If Minnesota decides its best path forward involves trading Ryan, Ober might be exactly the kind of veteran starter the organization needs to keep.
Do you believe Ryan and Ober are intertwined this winter? Leave a comment and start the discussion.
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