Every time a young star elsewhere finalizes an extension that keeps him on his team for longer than his typical six or seven club-controlled season, the natural reaction has been to use it as a framework for one Orioles star or another — none of whom have been signed to such contracts themselves.

Now, at least it feels realistic.

With the pending takeover of the club by David Rubenstein and a group of partners that, it’s fair to say, will have more resources at their disposal to fund baseball operations than John Angelos — who said nine-figure contracts would lead to massive ticket price spikes if the Orioles awarded them — the club now may have the wherewithal to do so.

Adley Rutschman, Gunnar Henderson, Jackson Holliday, and pretty much every Oriole (along with their representation) are likely watching closely.

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Enter Bobby Witt Jr., the second overall pick behind Rutschman in the 2019 MLB draft and now a standout shortstop for the Kansas City Royals at age 23. He signed a deal that, according to reports, will pay him up to $377.7 million over 14 years. Witt, who has four years of club control before free agency, will make $41 million over those four years (through 2027), then $100 million for the next three seasons before he has the first of four player options for $35 million per year through 2034. If Witt is still under contract at that point, the Royals can exercise a club option for an additional $89 million over three years.

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That means Witt can make $141 million over seven years — just over $20 million per season — and decline the first of his player options at 30 years old if he feels he’ll be able to make more than the Royals would pay him in this contract on the open market, or go year-to-year at $35 million.

Given Witt’s profile as a young, dynamic shortstop, the natural inclination is to transpose such a deal onto Henderson or Holliday to keep them with the Orioles through their prime. Henderson, the reigning American League Rookie of the Year, had a similar 2023 offensively as Witt did, and at a younger age (22 vs 23). He is also one year further from free agency than Witt. Henderson is set to make the league minimum for two more seasons before reaching salary arbitration, and is on schedule to be a free agent after the 2028 season at age 27.

All that would factor into Henderson’s thinking on an extension. The salary for those first few seasons in which he’d be a free agent — $100 million over three years for Witt — would need to be high enough to justify the potential for a market-setting contract in free agency at an age when few premium talents make it to free agency. Bryce Harper and Manny Machado signed for an average of $25.4 million and $30 million per year as 26-year-old free agents ahead of the 2019 season, and Corey Seager was 27 when he signed a 10-year deal with the Rangers worth an average of $32.5 million ahead of the 2022 season.

Jackson Holliday takes the field for Norfolk. (Photo by Sydney Smith, courtesy of the Norfolk Tides.)
Jackson Holliday takes the field for Norfolk.

Witt’s deal takes away his potential to improve on that, and that’s something that Henderson’s representation — the Boras Corp. — rarely does. Instead, the firm led by agent Scott Boras prefers its top clients to reach free agency, where the open market can drive contracts higher. That’s likely a very attractive proposition for him with Henderson, to say nothing of Holliday, who despite not yet debuting, is the top prospect in all of baseball and, even on the most conservative timeline, would be a free agent at 27 as well.

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Anything can happen with a large enough offer, but it would have to be pretty significant for the players to pass up this opportunity with their current representation.

Rutschman, a college draftee who is two years into his major league career and turns 26 on Tuesday, remains the club’s most obvious extension candidate for a variety of reasons. First and foremost, he is the standard-bearer for this Orioles turnaround, with his arrival heralding its beginning and his overall elite performance as a catcher making him every bit worth the top billing he’s received on the team.

It’s the performance aspect that would warrant the money, though the intangibles help, and the reality for the Orioles and Rutschman indicate whatever extension resources they have allocated should be directed at him.

He may only have one real crack at free agency, at 30, and there’s always going to be an unfavorable projection curve for him extending out from that point in his career, given the physical toll catching has on long-term performance. Rutschman can solidify longer-term earnings without sacrificing much long-term upside, while the Orioles can lock in league-leading performance at a premium position for something like seven or eight years. Keeping Rutschman around would have the secondary benefit of his continued presence as a symbol of continuity, should others be traded ahead of free agency or reach it.

Baltimore Orioles relief pitcher Yennier Cano (78) speaks with catcher Adley Rutschman (35) after the final out is secured in the ninth inning of a baseball game against the Tampa Bay Rays on Sunday, Sept. 17, 2023. (Ulysses Muñoz/The Baltimore Banner)

There are other options for more modest deals on the roster, and the Orioles could always attempt a pre-debut deal with the next wave of prospects on the horizon.

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Let’s not kid ourselves, though: This has always been the case. If the Orioles’ baseball operations department was as fully funded as we are led to believe, they probably would have agreed to an extension or two like this for now. Instead, the low salaries enforced by baseball’s collective bargaining agreement have benefited the Orioles, and their young talent has been left to wait.

But if the small-market Royals can now dole out an extension like this — which brings their luxury tax payroll for 2023 to over $160 million — so, too, can the Orioles, especially as new ownership begins to make its stamp on the club.

The question remains, though: Who will accept one?

Jon Meoli is the Baltimore Banner's Orioles columnist and head women's ice hockey coach at Loyola University Maryland.

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