From the moment that Gunnar Henderson made his Major League debut with the Baltimore Orioles back in 2022, fans have been clamoring for the team to sign him to a contract extension.

After successfully extending catcher Samuel Basallo, Orioles owner David Rubenstein spoke about wanting the organization to do more. The Orioles previously reached out to Henderson’s camp about a potential extension, but so far, there has not been any indication that such an extension is remotely close to happening.

Not only does Henderson employ Scott Boras — who is notorious for avoiding contract extensions for his young clients — but he also isn’t even arbitration-eligible until next season. Another potential wrinkle, however, comes from recent comments Henderson made when asked about his future. He said that he wants to be in a “winning culture”. Given the current state of Baltimore’s roster, that could prove to be a real hurdle.

Gunnar Henderson put the ball in the Orioles’ court after saying he wants to play in a “winning culture”

Obviously no player is going to come out publicly and say that he’s looking for the biggest payday — though that’s always part of the equation. While it’s possible that money will be the biggest driving force for Henderson, the fact that he went out of his way to say that winning is his No. 1 priority may not bode well for Baltimore’s extension chances unless they turn things around.

While the Orioles have played better under interim manager Tony Mansolino, they’re still at the bottom of the AL East. All-Star catcher Adley Rutschman could be traded this offseason and Baltimore’s front office has yet to demonstrate they can build a quality and sustainable pitching staff. If you’re in Henderson’s shoes, do you think that the Orioles are going to be contenders?

In that same meeting with the media, however, Henderson was open to extension talks and said he would be happy to look at an offer. That sort of implies Henderson hasn’t received an extension offer yet from the Orioles, at least not one worth discussing.

Baltimore will almost certainly throw out a number this offseason, but their first order of business should probably be to show that they can build a winning team. If they can’t do that, the dollars and cents may not matter.