The Gift That Keeps On Giving
Chris Davis walked away from baseball in August 2021. He was done swinging. But Baltimore Orioles? They’re not done paying him. Not by a long shot. Not until 2037—a year when some of Davis’s former teammates will be coaching in the majors and his kids might be thinking about college.
This isn’t a hypothetical. This is the actual calendar the Orioles created when they signed Chris Davis to a seven-year, $161 million contract back in 2016. The deal included $42 million in deferred payments structured to hit Baltimore’s books over 16 years, from 2023 all the way through 2037. That’s $9.16 million annually from 2023 to 2025, then $3.5 million per year from 2026 to 2032, and finally $1.4 million each season from 2033 to 2037.
By the time the final check clears, Davis will have been retired for 16 years. The contract will have spanned more than two decades. And Baltimore will have paid a player who last took a professional at-bat longer ago than some of their current prospects were born.
How One Deal Became a Cautionary Tale
The Chris Davis contract didn’t start as a joke. In 2016, when the Orioles signed the slugger, he was a legitimate power threat—a guy who could hit 30 home runs and drive in 100 runs. The market was paying for that potential, and agent Scott Boras negotiated a deal that pushed money into the future, a tactic that made sense for a Baltimore organization trying to manage cash flow during the initial years.
What nobody predicted: Davis would hit .168 in 2018, the worst average for any qualified hitter in modern baseball history. His knees deteriorated. His swing never recovered. By 2021, the Orioles had already written off the investment, and Davis himself recognized the writing on the wall. Better to retire than chase ghosts.
But the money? The money doesn’t retire. It’s locked in. It’s real. It’s coming.
The Orioles are paying Davis roughly $1.4 million to $9.16 million per year to not play baseball. He’s not in uniform. He’s not in the clubhouse. He’s not even watching from the broadcast booth. He’s simply cashing checks while Baltimore’s current roster tries to build something better.
Why This Still Matters in 2026
You might wonder: why bring this up now? Because the Chris Davis story is a masterclass in why front offices obsess over contract structure. Because it shows why teams are more careful about deferral clauses than ever. Because it’s a reminder that when you sign a player for $161 million, you’re not just betting on talent—you’re betting on durability, health, and the unpredictable arc of a human body.
The Orioles aren’t unique. Baseball has a long history of teams paying players who’ve already left the game. Bobby Bonilla has been cashing $1.19 million checks from the New York Mets every July 1st since 2011, and he’ll keep doing it until 2035. The New York Yankees paid Derek Jeter well into his post-retirement years. These deals happen because teams and players agree to spread money across time—a financial tool that made sense at the moment but can look absurd years later.
What makes Chris Davis different is the sheer length of the tail. Sixteen years of payments. A player who retired at 35 will still be collecting from Baltimore when he’s in his early 50s. The money will outlast his competitive window by a generation.
For Baltimore Orioles fans, it’s a bitter pill—a reminder of resources tied up in a deal that never delivered. For Davis, it’s security. For everyone else, it’s a cautionary tale about how contracts work in professional baseball: once the ink dries and the deferrals are locked in, nobody can undo the math. Not even retirement.
The 2037 payments are coming. That’s not speculation. That’s the deal.
The number: Chris Davis will collect $42 million in deferred money from the Baltimore Orioles through 2037, 16 years after he retired in 2021.
