The Baltimore Orioles shocked the baseball world en route to a 2023 AL East crown. Their next bold initiative? Signing two Scott Boras clients to contract extensions before they hit free agency.

Speaking to the media on Thursday at MLB's Winter Meetings, Boras joked that the Orioles reach out about deals for his clients Gunnar Henderson and Jackson Holliday “only once or twice a day,” per The Baltimore Banner's Andy Kostka.

Boras went on to elaborate about those kinds of conversations. “Those kinds of things, obviously we listen, and [Orioles GM] Mike [Elias] and I talk a lot. Obviously, our job is to filter those phone calls and relay them to the player, and kind of discuss it and see if it’s something that the player himself is interested in.”

While Boras will listen, his modus operandi as an agent hasn't been to act under those circumstances. Boras clients, especially his marquee ones, typically run down their contracts in order to reach free agency. At that point, the hope is that a bidding war between teams breaks out.

Too soon?

Causal MLB fans are most likely more familiar with Henderson. The infielder made his debut in 2022, appearing in 34 games for the Orioles. He broke out last season, producing a 6.2 WAR campaign and capturing the AL Rookie of the Year Award, as well as a Silver Slugger Award as a utility player.

Gunnar Henderson, Orioles

If you don't know Jackson Holliday, don't fret. While he's a top prospect in all of baseball, he hasn't yet made his MLB debut.

While it might sound premature to sign a player who has never seen a pitch above Triple-A, plenty of teams look to lock young talent into long-term deals as a cost control measure.

The latest to do so was the Milwaukee Brewers, who weeks ago awarded top prospect Jackson Chourio with a deal worth over $80 million despite Chourio having yet to make his MLB debut as well.