4 extensions the Orioles must prioritize when new ownership takes over

Whenever any team has the amount of young talent that the Baltimore Orioles have, it is fair to wonder if there is any way for the team to lock at least some of these guys down long-term. Giving young players extensions long before they come close to running out of team control is all the rage these days, with the Braves, White Sox, Brewers, Mariners, and many other teams all getting notable early deals done in recent years.

Unfortunately, committing long-term money -- even on team friendly deals for absolute studs -- just wasn't going to happen when the Orioles were owned by the Angelos family. However, with Baltimore slowly moving towards a change in ownership that should be more open to spending a bit (in theory), it is time to start thinking about who Baltimore needs to try and commit to in the near future.

Here are 4 extensions the Orioles need to make once their ownership situation is locked in

In fairness, all of these guys are players that the Orioles should be trying to extend, regardless of their ownership situation. All represent the future of Baltimore as a baseball team, and all are supremely talented. Extending all of them is probably a stretch, especially given the agents involved (more on that in a bit), but here are the extensions the Orioles need to try locking in right now.

Gunnar Henderson

A pretty easy place to start is with the reigning AL Rookie of the Year, Gunnar Henderson. Henderson was a revelation last year while accumulating 6.2 rWAR thanks to strong defense, posting an .814 OPS, and cranking 28 homers. Would it be nice if he hit for a bit of a higher average? Sure, but it is important not to overthink this one too much. Henderson is one of the best young players in baseball period, and the Orioles need to try and keep him for as long as possible.

However, there is a big wrinkle in this plan: Scott Boras. Yep, Henderson's agent is the agent that is the least likely to negotiate an early contract extension. To the Orioles' credit, Boras' presence doesn't seem to have stopped Baltimore from trying to get extension talks going already. As long as Boras is willing to listen to offers, the Orioles need to keep trying, even if the odds are low that this duo will pass up big time free agent dollars down the line.

Grayson Rodriguez

If there is a weakness on the Orioles' projected roster over the next few years, it is in the starting rotation. The lineup looks to be in great shape for the foreseeable future, and the bullpen should be in a decent spot once Felix Bautista returns, but the rotation doesn't have anywhere close to the long-term depth Baltimore is going to need going forward, even if Orioles somehow find a way to convince the newly acquired Corbin Burnes to stick around.

That is where Grayson Rodriguez comes into play. Often overlooked because of the scope of Baltimore's position player strength, Rodriguez is not far removed from being one of the best pitching prospects in baseball while putting up nutty strikeout numbers in the minor leagues. While his big league numbers in 2023 were fairly pedestrian, he showed plenty of flashes of what he can do down the stretch, and with a new pitch poised to help Rodriguez take the next step in 2024, the Orioles should try to strike now.

Extending pitchers is inherently risky, given how prone to long-term injuries they tend to be. Rodriguez hasn't been immune to the injury bug himself, as a lat injury cost him a chunk of time in 2022 in the minor leagues. However, a scaled down version of Spencer Strider's extension with the Braves seems like a good place to start a conversation with Rodriguez.

Such a move would keep Rodriguez cost-controlled in the event that he does truly break out and remove the uncertainty of arbitration. Rodriguez is also probably acutely aware of the risky demographic in which he resides, and given that he isn't a Boras client, it sure seems like he could be open to securing his financial future without forcing the Orioles to break the bank.

Jackson Holliday

Speaking of players that haven't made their big league debuts yet, Jackson Holliday sticks out as the lone true prospect the Orioles should consider extending. Holliday is another case of a No. 1 overall pick living up to the hype. After being the top pick out of high school, he posted a .911 OPS in his pro debut, and then was even better last year in slashing .323/.442/.499 with 12 homers and 24 stolen bases.

At the moment, the biggest question is whether or not Holliday will make the Orioles' roster right out of camp. Given the way he has played this spring, the odds continue to look good that he will be in Baltimore on Opening Day. If the Orioles really want to get the best possible price on an extension for him, they really need to try to do so sooner rather than later.

Again, we encounter a familiar problem in Scott Boras, as he is also Holliday's agent. Boras' ties to the Holliday go back to Jackson's dad, Matt, and his playing days, and Boras definitely got his dad paid when the time came. It is also important to remember that to bring Holliday into the fold in the first place, Baltimore had to fork over the largest signing bonus ever given to a high school draft pick.

The odds are definitely stacked against the Orioles when it comes to a really early contract extension for Holliday, but they still need to try. As is the case with Henderson, Baltimore has been staying in touch with Boras about Holliday, and who knows? Maybe the two sides can work something out over the next couple of years. The closer Holliday gets to free agency, however, the less likely that any sort of extension could get done at all.

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