Gunnar Henderson just put the Orioles in a tough spot with Scott Boras style move

Several members of the Baltimore Orioles' young core showed up to the team's press conference last weekend to support their newly extended teammate Shane Baz. It's great for team chemistry to see so many of these young players who have only been teammates with Baz for a couple weeks showing up for his big moment.

And it's especially generous of some of the Orioles more marquee players to come, considering that by attending the press conference, they were walking into a room full of media members ready to ask them some potentially awkward questions about their own willingness to sign an extension.

Gunnar Henderson's presence at the press conference was especially noteworthy. Out of all the players on the team, Henderson is one the front office would most like to lock up long term on an extension. Just a week ago, Jon Heyman reported that Henderson had turned down an extension offer from the Orioles before the 2025 season.

Scott Boras, Henderson's agent, is MLB's premier super agent, known for ruthlessly pursuing the best and biggest contracts for his clients, and he's on the record saying that arbitration extensions are not in players' best interests.

Boras' clients have signed extensions before, but it's incredibly rare, and usually the player has to be the one to instigate the negotiations. Long story short, if a player is represented by Boras, he's going to make it to free agency and sign with whichever team offers him the biggest contract.

Gunnar Henderson may be open to an extension with the Orioles, but one remains unlikely.

Despite Henderson's stance on extensions already being strongly implied by his choice of agent, he was asked about his willingness to sign an extension with the Orioles. His response was right out of the Boras Corp playbook: "Any time they want to come my way, I'm open ears, but also my first priority right now is to win ballgames and do whatever I can to bring a championship to the Orioles. All of that stuff is secondary right now."  

From the agent's side, it's a perfect quote. It's right in the sweet spot. Act like you're not interested, and the fans could turn against you. Act like you're too interested and you'll create a media storm of questions directed at the Orioles that ends with them revealing the extension offer they made that was turned down.

"I'm open ears" is light-hearted, vaguely positive, and hard to follow up on. Orioles fans should prepare to hear different versions of "I'm open ears" several times over the next three seasons until Henderson reaches free agency.

For the Orioles' part, they should take him at his word, even if his word is being advised by Boras, and send him aggressive extension offers every couple of months. Boras still works for Henderson and has to show him all the legitimate contract offers the Orioles send over. So just do it, send over an extension worth $500 million, and see if he turns it down. If he does, no hard, no foul, and if he doesn't, then you've got your franchise shortstop locked up on a below-market long-term deal.