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The Orioles can do a big contract extension with somebody if even the Royals can do it

Kansas City announced a contract for Bobby Witt Jr. that could reach 14 years and $377 million

Mike Elias has to figure out who’s worth some big money and who might actually take it.
Karl Merton Ferron/The Baltimore Sun/Tribune News Service via Getty Images

There are times where it feels like a new interesting and exciting young player in the league gets a big contract extension from his team on a weekly basis. It is a trend that has made an impact all over the league, in big and small markets. One place this has not yet visited is Baltimore, where up to this point there has been nothing brought to fruition.

The latest of the big contract extensions came on Monday when the Kansas City Royals announced a contract extension with their shortstop Bobby Witt Jr. that could run for as few as seven years, if Witt exercises an opt out with close to $150 million already banked, and could go for as many as 14 years and $377 million, if the Royals exercise a three-year option available to them if the contract reaches its full 11 years.

That is the kind of commitment that it would be fun to see the Orioles make to somebody. As long as the franchise remained under the stewardship of John Angelos, this did not feel like it was a likely scenario, probably to the detriment of the team in the long run. Once new owner David Rubenstein and the rest of his ownership group take over, perhaps there can be a different philosophy from the front office about when is a good time to lock up young players and create a chance for them to be career-long Orioles.

Witt maintained a lot of hype for his talent as a player even after a rookie season where he posted a sub-.300 on-base percentage and had poor marks for his defense, leading to a 0.9 WAR debut season. However, he followed that up with a 4.4 WAR season where he batted .276/.319/.495, hitting 30 homers and stealing 49 bases while playing closer to average shortstop defense. That’s contributing in a lot of different ways.

Before the 2022 season, Witt was part of a big MLB prospect trio along with Seattle’s Julio Rodríguez and our own Adley Rutschman. Two of those three guys are now signed to big nine-figure deals, with Rodríguez guaranteed $119.3 million across a seven-year deal he signed last season that includes a player option that would kick the whole thing to twelve years and about $210 million.

These deals are not comparable ones for Rutschman, though, because Rodríguez signed his contract before his age 22 season and Witt has now taken the figurative big bag of money before his age 23 season. On the other hand, Rutschman turns 26 years old today, February 6, 2024. Without their new contracts, Rodríguez and Witt would have become free agents prior to their age 27 and age 28 seasons, respectively. Rutschman’s only on track to get this opportunity heading into his age 30 season.

The difference between these ages is not so stark on the actuarial tables of life expectancy. In terms of the timeframe of peak big league productivity, it’s a massive one, all the moreso because Rutschman is a catcher, and they are known for aging worse than many other types of players.

As much as it feels good to think, “Let’s sign Rutschman forever!”, the time before free agency math for Rutschman would probably mean it would take a nine-year contract to get him to give up potentially colossal arbitration salaries before hitting free agency payday years. Rutschman getting $35 million like Witt (or more) for years seven, eight, and nine and ages 32-34 is a riskier proposition for the team.

Perhaps Rutschman won’t age as badly as some, and it seems like the Orioles are trying to avoid this happening by not over-using him. Consider that in 2023, Rutschman caught 97 complete games and 934.2 innings overall. Last decade’s catcher of the future, Matt Wieters, was used heavily in his early years, culminating in 127 complete games and 1,201 innings caught in 2013. Wieters needed Tommy John surgery in 2014 and turned out to be done as an elite-level player after his age 26 season. This difference is not an “Extend him forever!” difference. Probably.

The Orioles do have “Extend him forever!” players based on their age and what they’ve already shown of their talent level. Those guys are Gunnar Henderson and Jackson Holliday. There is a simple problem with trying to think about extensions for these guys: They’re represented by agent Scott Boras, whose reputation for guiding his clients to free agency is known and who probably ends up with a selection of players who bring this desire into pro ball themselves.

An example of this in action is new Oriole Corbin Burnes, who was asked about testing free agency in his first interview with Orioles press and said, “I think I’ve been pretty honest in that being a year away from free agency is something everyone wants to get to. Everyone wants to pick where they will play.” I am in favor of every player getting his payday when and where he chooses, but it’s definitely less fun when your team has the #29 payroll in the league. Hey, some good news: After acquiring Burnes, the O’s are up to #25.

If it wasn’t for the Boras factor, Henderson’s value heading into last season was likely quite close to that of Arizona’s Corbin Carroll, who like Henderson was a 2019 draft pick as a high school kid and who ascended to the #2 prospect position, behind Henderson, for 2023. Each of these guys got about a month worth of action at the end of the 2022 season and did pretty well for themselves to springboard into rookie campaigns for 2023. These were the AL and NL Rookie of the Year winners.

Ahead of last season, Carroll signed an extension with the Diamondbacks that guarantees him $111 million over eight years. There’s a ninth year option that Arizona holds that would add a $28 million salary with a $5 million buyout, so that’s got a good chance of being a nine-year, $134 million contract. This was signed heading into Carroll’s age 22 season when he had 35 big league games under his belt. Even without considering Boras, Henderson’s price would be much greater than that now that he won the ROY. There would at least be some hope in the Rubenstein group backing up the armored car with sufficient stacks of Benjamins.

In a similar way, there’s a blueprint right there for a Holliday pre-debut contract now. Milwaukee Brewers outfield prospect Jackson Chourio, who’s #2 to Holliday on many prospect lists the same as Carroll was to Henderson last year, inked a deal that guarantees him $82 million over eight years, with two team options that could push it to ten years and $128 million. Chourio turns 20 next month, so just like Holliday, he’ll be playing his age 20 season this year. I would do that deal for Holliday right now, and surely so would Mike Elias. Neither one of us is the person whose opinion most matters.

There are people out there who refuse to give up on the possibility of signing one of these players to a contract extension. It’s true that there are extremely rare exceptions of Boras clients signing contracts before they hit free agency that give up some free agent years. Even these rare exceptions are concentrated in deals that happened after a player had hit arbitration, so the wild dreamers will still have to wait at least two years until Henderson gets to that point and then be disappointed by reality.

One more pre-2024 season contract extension has a decent comparison for an Orioles prospect. The Detroit Tigers have given a pre-debut deal to their infield prospect Colt Keith that guarantees Keith $29 million over six seasons, with Detroit holding options that could take it to a nine-year, roughly $50 million deal. Keith is very close in age and current prospect stock to Coby Mayo.

The obstacle to the Mayo deal is more that there’s nowhere to fit him on the roster right now. A prospect die-hard who’s not into continuing the Ryan/Ryan platoon at first base might insist on signing Mayo and discarding those other guys. I hope we can all accept the unlikelihood of Elias, or really any GM in this position, doing this.

Among the team’s more veteran players, it’s not easy to find a good extension fit even for something much more modest in years. Had Cedric Mullins not had a second half swoon last year, I think he and the Orioles could come together on a four- or maybe five-year deal starting this year. A version of 2023 that saw John Means return in July and pitch well the rest of the way would have had him as an interesting candidate to get a three-year extension right now. That is not what happened.

All of which leaves us right about where we started, and where I’ve been for at least the past year: It would be cool if the Orioles jumped on this trend and minted this era of the team’s Oriole for life, a guy who’s going to hang around through multiple eras, buy a house here, be a fixture after retirement.

For a variety of different reasons, there just aren’t any likely Orioles candidates for this right now. At least once Angelos is not calling the payroll shots, we might have some hope to get a good deal when the right young Orioles player does come along at the right time.