What the industry acknowledges across the board, is that Henderson will be dealt by the trade deadline, same as it was a year ago with Adley Rutschman, the only player Orioles failure baseball exec Mike Elias drafted ahead of Henderson on what\u2019s now an eight-season rebuild<\/a>. What\u2019s far less clear is when is the best time to deal Henderson given just how pedestrian his 2025 season was, all things considered, and just how much worse he was at the plate, in the field and on the base paths in 2026.<\/p>\n Some caution against \u201cselling low\u201d on a player viewed as an MVP candidate and 40\/40 guy just a few years ago. Others point out that there are only a few truly-motivated \u201cbuyers\u201d at the deadline each year but with Henderson cheap and young with two years of full control, his market after the World Series would be very robust.<\/p>\n I\u2019ve long been in the camp that auctioning him off at The Winter Meetings should be the goal, and then the other offseason priorities<\/a> can be set based off the return. Elias is at his miserable worse trying to develop fallen assets on the fly and make cogent in-season moves. And one of the smartest baseball people I know, Fangraphs data scientist and lifelong Orioles fan, Dan Szymborski, tends to agree with me that moving Henderson ASAP makes the most sense.<\/p>\n \u201cI think teams are still going to look at Gunnar Henderson despite his season and there’s going to be a lot of belief that he’s still a star,\u201d Szymborski, one of the brains behind Fangraphs ZIPS projections<\/a>, said on \u201cThe Daily Flock\u201d this week. \u201cAnd he can fetch a lot. <\/p>\n \u201cI think there’s probably just myriad opportunities to trade Henderson if you’re going to go that route, and they probably waited a little long with Rutschman, if you were going to trade him and not extend him.\u201d<\/p>\n A Massive Return Sep 23, 2026; Baltimore, Maryland, USA; Baltimore Orioles shortstop Gunnar Henderson (2) cannot field the ball during the third inning in Game 2 of a doubleheader against the Toronto Blue Jays at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | IMAGN IMAGES via Reuters Connect<\/p>\n Despite Henderson having a league average offensive season for the most part and seeming visibly frustrated, throwing bats and helmets and letting his hitting issues bleed into the field, MLB execs know what a joke Orioles player development is. And what a joke their coaching staffs are. <\/p>\n There is a speed\/power\/contact demon still in there (but one this group can’t reach or unlock), and many, many GMs will believe they can release it, whether they view him as a shortstop of third baseman. Szymborski, who makes his living quantifying overall player value in the present and projecting for the future, was adamant the Orioles could get a significantly better package of players and prospects than the haul Elias was lauded for getting in return for Rutschman<\/a>.<\/p>\n \u201cI think you could get more for him,\u201d he said. \u201cHenderson’s upside is higher \u2026 A Henderson package would be just really, really solid. And I think if you can’t extend him, you have to talk about it.\u201d<\/p>\n With not just teams in immediate-go-for-it mode, and early in the offseason when all clubs still have ample time to address needs, there is every reason to believe the Orioles could get MLB-ready help as well as prospects; the Rutschman deal was essentially all for teenagers who are years away from really making a dent in Baltimore.<\/p>\n One For One Swap? Aug 18, 2026; Minneapolis, Minnesota, USA; Minnesota Twins pinch hitter Byron Buxton (25) celebrates his run against the Atlanta Braves in the eighth inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images | IMAGN IMAGES via Reuters Connect<\/p>\n Szymborski agrees with me that fixing centerfield from outside the organization is a sweeping, primary item that must be addressed this offseason and, quite likely, early this offseason. I firmly believe trading two years of Henderson\u2019s career for two years of Byron Buxton\u2019s make sense \u2013 baseball and financial as explained in depth here<\/a> \u2013 and the analyst did not disagree. Especially from the Orioles side of things.<\/p>\n \u00a0\u201cI don’t think you’re crazy,\u201d he said. \u201cI just don’t know if the Twins will do it. The Twins are a very conservative organization, and they love having Buxton, and they love that he wants to be there.\u201d<\/p>\n![\"Baltimore](\"https:\/\/www.newsbeep.com\/au\/wp-content\/uploads\/2026\/10\/01m4xt8f9ecgxmsvzhzj.jpg\" "\\"Baltimore")
<\/p>\n![\"Minnesota](\"https:\/\/www.newsbeep.com\/au\/wp-content\/uploads\/2026\/10\/01m4xt0e8ed37hwh5kdq.jpg\" "\\"Minnesota")
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