Birdland Grows Restless for That First Contract Extension

While I usually wait a bit longer into the season to do full-on opinion pieces, I felt the need to make an exception for this particular topic. It’s one that O’s fans are talking about all the time.

So, where are the extensions? Why haven’t we seen any yet?

Before we begin, we need to set the stage for these talks. The Orioles have this amazing young core of players. Some are still coming up through the minor. Others are becoming established big-leaguers in front of our eyes. And a couple (you know who) are already stars. When this happens, the front offices that drafted/signed and developed these players will usually race to the table to get an extension done. This is done to ensure that the player is with the team long-term, but it is also done as a money-saving move by the team. You pay the player at a higher rate early on so that he becomes much cheaper later.

This style of extension has been made popular by the Atlanta Braves, who have managed to sign nearly every one of their young players to these cheap contracts. Think about every good offensive player in Atlanta: they’re likely already signed to some kind of intelligent, cheap extension. It isn’t just the Braves though; nearly every single franchise in the MLB has inked at least one of these extensions. This even extends to the smaller markets, as teams like the Rays and the Royals have managed to lock up some of their young talent as well.

Despite the prevalence of extensions across baseball, the Orioles, under Mike Elias, have yet to extend a single player. With such a talented core, one would expect at least one extension, right? Yet, to this point, it hasn’t happened, and fans are understandably vocal about it.

Under every highlight of Gunnar Henderson and Adley Rutschman, you’ll find comments like, “Extend Gunnar,” “#ExtendAdley,” Why haven’t they extended this guy yet,” or my personal favorite, “Orioles are poverty because they haven’t extended anyone.”

Before this year, it was easy to place blame. Fingers pointed to the same place every time something went wrong with the team, the owner’s box. John Angelos’s thriftiness made him an easy scapegoat for the lack of extensions. John hasn’t controlled the team for months though. Angelos is gone, he can’t hurt Orioles fans anymore, and David Rubenstein is here to save the day.

But, as of the day I write this article on May 19th, 2024, there still hasn’t been a single extension.

What scares O’s fans is that we’ve heard nary a peep of a rumor that talks are even going on. We all also still have PTSD from watching the last great Baltimore core walk out the door with little to nothing in return. If that happens again with new ownership…well, the mere thought wakes me up out of my sleep.

What we need to remember is that extensions aren’t easy.

So, let’s talk about what might be holding them up.

Note: When we talk about extensions, I am talking about the young core, not the team’s veterans, unless stated otherwise.

Rubenstein Just became the Owner

The first point is the most important one. While it may seem a bit longer because we first heard these rumors over the winter, and then MLB took its sweet time approving the transfer to Rubenstein, he has only been the owner for a little over two months. He was officially approved the day before Opening Day. That is a ridiculously short time in the grand scheme of things.

Rubenstein also has had plenty to do in the day-to-day life of a new owner, getting familiar with his new role. He can’t spend every waking second trying to get extensions done. We need to give him time. There’s plenty of it.

Extension Talks Don’t Typically Happen Mid-Season

This flows seamlessly into my next point: these extensions take a ton of time and effort, and because of that, they don’t usually happen mid-season. Players are locked into their day-to-day routines and the grind of the season, and don’t want to be bothered by their agents pestering them about making life-altering decisions. There are exceptions to the rule (Adam Jones), but for the most part, contracts are finalized in the offseason or Spring Training. Rubenstein’s never been the owner during the offseason. He’s had zero time to get anything done!

For example, talks for KC’s massive Bobby Witt Jr. extension took from the end of last season until February, nearly six months. That’s three times as long as Rubenstein has owned the team. By the way, just because we aren’t hearing anything from the rumor mill about extensions doesn’t mean there aren’t discussions. The Orioles, under Mike Elias, keep things very close to the vest, and almost nothing leaks out. If a big extension were imminent, we probably wouldn’t hear about it until someone like Jeff Passan or Ken Rosenthal tweeted about it.

Again, there are exceptions to the rule, but usually, big-money extensions don’t happen mid-season.

It Takes Two to Tango

This point is hard to accept but it is the truth. The trend around MLB has made these extensions look like a foregone conclusion (with an owner that will pony up the dough), but they are far from a given. The players have to want to stay, and the Orioles might have lost out on a cheap extension chance for some of their players already.

Angelos being Angelos probably cost the Orioles a chance at a team-friendly extension for Adley. Remember, the Braves extensions were all cheap relative to the player’s talent level. Is Rustchman accepting something like that right now? Maybe I am wrong but I feel like if Adley wasn’t asking for a record-breaking extension, it would have happened by now.

What about Gunnar, then? Well, look who is agent is. Scott Boras (who also represents Jackson Holliday and Corbin Burnes).

Why does Boras being Gunnar’s agent matter? It matters because his clients, as a general rule, hit free agency. It matters because Gunnar, like Adley, isn’t accepting a cheap deal. It will cost more than Witt’s extension to get Gunnar done. KC only had to deal with Witt’s father, not the most powerful agent in the sport.

(As for Burnes, he’s absolutely, 100% testing free agency. The O’s only chance at seeing him suit up for them in 2025 is if they can win the bidding war for his services.)

There are others who could sign extensions, of course. I think a sneaky first extension candidate could be Colton Cowser or Jordan Westburg. They would be cheaper than Adley or Gunnar at this point, and they don’t have Boras as agents. Another one I could see is Grayson Rodriguez.

Despite it all, I think extensions will be coming, but it is hard to say when. Maybe we should reserve judgment until these guys get somewhat close to free agency and Rubenstein has had time to negotiate these deals. Let’s give Rubenstein at least a full offseason in control before we get too upset about the lack of movement on the contract front.

I am with you, Birdland. I want to get that notification on my phone that someone – anyone – has signed an extension to stay in Baltimore. It’s going to HIT. I want to be reassured that it is truly the “Next Chapter.” I want to see the ball get rolling.

But we all need to relax and remember that these deals take much more time, effort, and perhaps even money, than we’d like them to.