Boras on possible Orioles extension for Henderson: ‘I listen’

NASHVILLE—The most powerful agent in baseball, Scott Boras, has a couple of well-known Oriole clients. Gunnar Henderson, who was the unanimous winner of the American League Rookie of the Year award, is one of them, as is top prospect Jackson Holliday.

As always, Boras holds court in an overcrowded scrum during the latter part of the Winter Meetings, and when Boras was asked on Wednesday if Orioles executive vice president/general manager Mike Elias had discussed a possible extension for Henderson with him, he joked: “Only once or twice a day,” but quickly grew more serious.

“With those kinds of things, I listen,” he said. “Mike and I talk a lot and, obviously, our job is to filter those phone calls, relay them to the players and we discuss it, see if it’s something that the player himself is interested in.”

Boras usually advises his clients to eschew extensions and test the free agency market first, though a few — Jose Altuve, Xander Bogaerts, Stephen Strasburg and the Los Angeles’ Angels Jered Weaver — did sign extensions before hitting free agency.

He also represents Holliday, the top minor league prospect in baseball whom the Orioles made the overall No. 1 pick in 2022.

On Tuesday, Elias said that it was “definitely a very strong possibility” that the 20-year-old Holliday could start 2024 with the Orioles.

Holliday, whose father Matt is credited with mentoring him, sped through the minor leagues, spending the last few weeks of the season with Triple-A Norfolk after beginning the season at Single-A Delmarva.

“You watch him hit, you watch him play. There’s a calmness to Jackson, no matter where he plays,” Boras said. “He’s very familiar with the major leagues because of his father. There is no ballpark he’s not comfortable in. Chronological age really doesn’t matter. He has the emotional and physical tools to compete at the major league level. I think that’s best for the Orioles to decide. Certainly he’s someone he’s knocking at the door.”

Boras also represents some top free-agent pitchers: Blake Snell, the unanimous selection as National League Cy Young Award winner; Jordan Montgomery, who pitched for the World Series champion Texas Rangers; and Hyun Jin Ryu, the left-hander who spent the last four seasons with the Toronto Blue Jays.

“Mike and I have talked a good bit about many of the pitchers on our roster,” Boras said. “They are certainly letting us know they certainly want to add pitching depth to their rotation.”