It has been an eventful couple months on the extension front. Tyler Soderstrom and Jacob Wilson for the A's, Jesús Luzardo and Cristopher Sánchez in Philadelphia, Nico Hoerner and Pete Crow-Armstrong in Chicago — everyone's gettin' paid. And that's only scratching the surface. Hopefully for Baltimore Orioles fans, next up is All-Star shortstop Gunnar Henderson.
Henderson is 0-for-8 to start the year, but anyone panicking over a two-game sample size needn't do so. The 24-year-old was awesome in the World Baseball Classic, even if he only played half the time, and his track record is damn near unimpeachable at such a young age. Last season was a slog as Henderson battled through various injuries, but even a "down" year saw him in the 89th percentile for expected batting average, with a .787 OPS and 121 OPS+.
Can the Orioles sign Gunnar Henderson to a contract extension?
It gets harder and harder to sign premium talent before free agency these days. The market expands every year. The bar gets raised constantly. If Henderson were to hit the open market tomorrow, he's probably looking at $400 million offers. That said, he's not a free agent until 2029. The Orioles are probably buying out a few years of free agency in exchange for a massive raise over his current arbitration rate, which sits at $8.5 million.
So yes, Baltimore has the means to get something done. The O's were allergic to significant long-term investments for so long, but this winter saw them take a real run at Kyle Schwarber in free agency. When that fell through, the O's inked Pete Alonso to a five-year, $155 million contract and eventually extended newcomer Shane Baz at five years and $68 million.
There is undoubtedly a limit to what the Orioles can (or will) spend, and there are other viable extension candidates on the roster, such as Jackson Holliday, Adley Rutschman and Samuel Basallo, all of whom are probably cheaper at this current moment. Still, Henderson is the engine driving Baltimore's World Series hopes, so if there is a priority extension in that clubhouse right now, it needs to be him.
Henderson will not accept anything short of a market reset. It will not be easy to agree to terms, especially this early in his prime. But it's possible, as this offseason has proved time and time again. All it takes is the front office ponying up in a way it never has before. What could go wrong?
The biggest shortstop contracts in MLB right now
Shortstop happens to be a premium position. Maybe the premium position. So naturally, the Orioles are up against some daunting recent history here.
Player | Years | Total money | Age at signing |
|---|---|---|---|
Francisco Lindor | 10 | $341 million | 28 |
Fernando Tatis Jr. | 14 | $340 million | 21 |
Corey Seager | 10 | $325 million | 27 |
Trea Turner | 11 | $300 million | 29 |
Bobby Witt Jr. | 11 | $288.8 million | 23 |
Carlos Correa | 6 | $200 million | 28 |
Willy Adames | 7 | $182 million | 29 |
The best comparison points for Gunnar Henderson are probably Fernando Tatis Jr. and Bobby Witt Jr., both of whom signed many years before free agency — and both of whom were paid top-of-market price to spend the meat of the careers in one place. Tatis eventually moved to right field; Witt is the crème de la crème when it comes to fielding his position. Henderson should spent the next half-decade comfortably at shortstop, but he's far from elite with his glove (-3 Outs Above Average in 2025). A move to third base or the outfield sometime down the road is not out of the question.
Henderson's representation will almost certainly point directly at Witt's contract when negotiating with the Baltimore suits. He's currently about a year older than Witt was at the time of signing; Henderson's résumé isn't quite as fleshed out, but he finished fourth in MVP voting as a 23-year-old. The market also expands over time. Inflation, baby!
The alternative for Baltimore is probably a higher AAV and fewer years. Witt's contract was a massive underpay in hindsight, at least relative to his current open-market value. He'd get $500 million easy as a free agent. Henderson is currently on track to hit free agency as a 27-year-old. If he wants to boost his current salary but still test the market in his prime, something like a six-year deal — one that erases two years of arbitration and puts him in free agency around 30, when he can still get a bag — could be worth exploring for both sides.
It's worth mentioning the Scott Boras factor. Henderson's infamous agent historically avoids extensions like the plague. Boras wants to extract maximum value in free agency, when multiple teams can bid each other up. The O's will need to put forth a strong enough offer not just for Henderson, but for Boras. That means some of these team-friendly deals, like PCA's in Chicago, just will not happen.
At the end of the day, Henderson should accept something in line with his market value, which is probably $35 million-plus annually. Vladimir Guerrero's 14-year, $500 million extension in Toronto is another point of comparison, but Henderson is younger and he plays a more valuable position. Do not be shocked if he resets the market, if the O's want to get feisty and issue a statement of intent to the rest of the league. I think we are all a little skeptical of Baltimore actually stretching their wallet that far, but crazier things have happened. That Pete Alonso contract was unthinkable a year ago.
Predicting Gunnar Henderson's next contract
Final prediction: 14 years, $510 million
If the Orioles want to lock down Henderson for the remainder of his prime (and probably his entire career), it will require a bold investment on this scale. This comes out to roughly $36.4 million annually through Henderson's age-40 campaign, assuming the contract begins in 2027. That sort of hardline commitment could coax even Scott Boras into an agreement, especially since Henderson isn't coming off of his absolute best season.
This may feel impossibly risky, but it's the going rate for superstar talent. Bryce Harper, Trea Turner, Vladdy Jr., Mike Trout, Shohei Ohtani, Juan Soto — all these dudes get paid through their late 30s and sometimes early 40s in order to guarantee their contributions from 25-35. The O's will no doubt suffer on the back end of such a contract, but if it gets them a couple MVP campaigns and a World Series push, which Henderson is more than capable of, you won't find many fans (or front office personnel) complaining.