Reality has hit the Baltimore Orioles hard, and it’s easy to feel sympathetic for them. In an era of superteams, the O’s did their best to assemble a homegrown young core, with Adley Rutschman and Gunnar Henderson headlining a group that would ideally challenge the Yankees and Astros in the American League.
Instead, the Orioles just traded Rutschman to the Red Sox, and now a Henderson move feels inevitable. He has just two years of team control remaining beyond 2026 and is represented by Scott Boras, whose sole duty is to ensure his clients get paid the big bucks. Whether the Orioles would offer Henderson a meaningful long-term deal, especially as they potentially near another transition period, remains to be seen.
ESPN’s Buster Olney sounds skeptical, telling the "Just Baseball Show" that Henderson likely won’t re-sign with the Orioles. The fifth-year shortstop has not publicly commented on his plans, and there are no indications that the Orioles intend to offer him a new deal within the coming months.
For this list, we’re ranking the teams based on Henderson’s fit and how Boras would likely feel about a potential extension. We’re also operating under the assumption that Henderson would remain a shortstop, so there’ll be no instances of us moving him to another position solely to force a trade.
5. Houston Astros
Would the Orioles and Astros be open to swapping Henderson for Jeremy Peña? The latter only has one year of team control left, so Houston would have to include something else of value to get a deal done. But Peña's offensive numbers have taken a significant jump; he owns a career-high .879 OPS entering Aug. 7, and his strikeout and walk rates are both well above his lifetime averages.
Peña turns 29 in September, though, whereas Henderson is only weeks removed from his 25th birthday. The financial commitment to Jose Altuve, as well as a likely impending extension for ace Hunter Brown, could make this difficult. Then again, the Astros have proven they’re not afraid to be aggressive in trades.
4. New York Yankees
George Lombard Jr.’s arrival isn’t the sticking point here. Jazz Chisholm is a pending free agent, and Ryan McMahon only has one year of team control left. However, McMahon has barely been a replacement-level third baseman, and he’s almost exclusively manned the hot corner since the start of 2022. Turning him into a backup utility man is far easier said than done.
There’s also the Anthony Volpe question. Brian Cashman and Aaron Boone are fiercely loyal and stubborn, so Yankees fans should prepare to see Volpe remain in pinstripes to start the 2027 season. Boone has already confirmed that Volpe will see action at second base during his time at the Triple-A level.
An infield of Ben Rice, Volpe at second, Lombard at shortstop and Henderson at third certainly sounds interesting. But given the Yankees’ luck, it’s fair to wonder which of the four would get hurt first.
3. St. Louis Cardinals
Assuming that they plan to keep JJ Wetherholt at second base, Henderson immediately makes sense for a Cardinals team potentially nearing the end of its rebuild. Just because they’re quickly falling out of Wild Card contention doesn’t mean the front office shouldn’t pursue a splashy trade or signing this offseason.
Henderson would mark an upgrade over Masyn Winn, who is under team control through 2030 and should be part of the Orioles’ asking price. Don’t read too much into his diminutive 5-foot-9, 185-pound frame. Winn was a plus defender in 2024 and 2025, though his numbers have taken a hit this year. If the Orioles are truly open to moving Henderson, then they could do a lot worse than Winn as his replacement.
2. Toronto Blue Jays
Now we’re talking. Unfortunately for Canadians who might feel otherwise, Ernie Clement is not a viable long-term second baseman. Andrés Giménez’s hitting numbers have taken a massive decline since joining the Blue Jays last year, though his defensive reputation more than speaks for itself.
Giménez has extensive experience at second base, including manning the position last year when Bo Bichette was healthy. This would be an interesting move for a Blue Jays team that has repeatedly proved that they’ll spend in free agency.
1. Los Angeles Dodgers
Let the rich get richer, right? Any All-Star should be demanding a trade to the Dodgers so long as there is space for them — or, in other words, anyone who wouldn’t be limited solely to DHing. You’re not getting Shohei Ohtani out of the lineup that easily.
Mookie Betts appears to be on the decline, and he turns 34 in October. Moving Betts back to second and giving Henderson the reins at shortstop sounds right up their alley, as does having Betts return to the outfield so the Dodgers can add both Henderson and Chisholm. Such is life in a sport without a salary cap.
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