Orioles learned a painful lesson with Gunnar Henderson and can’t repeat it

The Baltimore Orioles surprised folks last year by locking up top prospect Samuel Basallo to an eight-year extension when he didn't even have a week of MLB service time under his belt. They may look back with regret and wish they had signed shortstop Gunnar Henderson to an extension rather than Basallo.

Baltimore reportedly made Henderson an extension offer last spring, but they were not able to work out a deal. It's unclear if talks are ongoing or if anything is in the cards, but it feels like the Orioles already waited too long to get something done.

Orioles may be too late to the party on Gunnar Henderson

After the Orioles failed to get something done with their star shortstop, he went on to have another solid season in 2025, hitting .274/.349/.438 with 17 home runs and 68 runs batted in. The power numbers were down compared to the two previous years, but he is still unquestionably a great shortstop. He may just be a tweak or two away from inserting himself back into the American League MVP conversation.

He certainly ratcheted up the pressure on the Orioles front office with a solid performance for Team USA in the World Baseball Classic. He had six hits in 15 at-bats including two home runs so maybe the power is due for a resurgence in 2026.

The problem for Baltimore is that if Henderson does have a big season, that gives him less incentive to sign an extension. Maybe he just wants some stability and wants to know he will be with the Orioles for a long time, but if agent Scott Boras gets in his ear he could easily talk him into waiting until after the 2028 season when he becomes a free agent.

It's tough to see the Orioles being able to compete in a bidding war for Henderson if he does hit free agency. The team proved this past offseason that it is willing to spend big on a guy like Pete Alonso so maybe they'd give it a run, but there's a chance Henderson will be hitting the market as a shortstop in his prime. A lot of teams are going to want to throw their hat into the ring for his services.

The Orioles should keep on trying to work on an extension so they do not lose him, but it already feels like the ship may have sailed on that front.