Last Updated: June 17th, 2026 by Michael Griffin
Baseball contracts aren’t just about the money – they’re windows into the soul of America’s pastime, revealing the quirky personalities, unique demands, and sometimes downright bizarre negotiations that make the sport so fascinating. From mustache maintenance allowances to bulldozer bonuses, these contract clauses prove that when it comes to baseball deals, the truth is stranger than fiction.
Don't lose this article. Enter your email below, and I'll send it to you right now. Plus, we'll send you other unbelievable stories from baseball's past.
Charlie Kerfeld’s 37 Cases of Orange Jello
In 1987, Astros reliever Charlie Kerfeld, who looked like a mix of Harry Carey and Drew Carey, insisted his new contract be for $110,037.37 – matching his uniform number (37) – and include 37 cases of orange Jello. The Astros, perhaps recognizing the PR value of such an unusual request, happily obliged. Kerfeld’s sweet tooth became the stuff of baseball legend, proving that sometimes the smallest contract details tell the biggest stories.
Rollie Fingers’ Mustache Saga
When Charlie Finley offered his Oakland A’s players $300 to grow mustaches in 1972, Rollie Fingers took it to the next level. His iconic handlebar mustache didn’t just earn him the initial bonus – he negotiated a $100 weekly maintenance allowance into his contract. That perfectly waxed handlebar became not just a fashion statement but a pioneering moment in sports marketing.
Troy Glaus’ Wife’s Equestrian Insurance
When negotiating his contract, Troy Glaus made sure it included insurance coverage for his wife’s equestrian activities. While most players focus on protecting their own athletic pursuits, Glaus ensured his wife’s passion for horseback riding wouldn’t be left unprotected.
A.J. Burnett’s Luxury Transportation
A.J. Burnett made sure his wife traveled in style, negotiating eight annual round-trip limo rides into his contract. While private jets might grab headlines, sometimes it’s the ground transportation that really shows who’s thinking about the details.
George Brett’s Real Estate Deal
The Royals helped George Brett become a landlord by including an apartment complex as part of his contract. Talk about thinking beyond your playing days – Brett turned his baseball success into real estate prosperity with one clever negotiation.
Carlos Beltran’s Vision Enhancement
Beltran’s contract included a $1.5 million ocular enhancement device to help improve his vision at the plate. When you’re paid to hit a small white ball traveling at 95 mph, every visual advantage counts.
Hiroki Kuroda’s Family Interpreters
Going beyond the standard interpreter provision, Kuroda negotiated to have interpreters not just for himself, but for his entire family. This thoughtful clause helped ensure his whole family could navigate life in America comfortably.
Manny Being Manny’s No-Trade Insurance
During his $160 million Red Sox contract, Manny Ramirez had a unique “me too” clause – if any other player got a no-trade clause, Manny automatically got one too. Classic Manny being Manny, ensuring he’d never be left out of any perks.
Turk Wendell’s Numerical Precision
Wendell, who wore number 99, insisted his three-year contract be worth exactly $9,999,999.99. Sometimes superstition and salary negotiations create perfect harmony.
Bobby Bonilla Day
The most famous deferred contract in sports history pays Bonilla $1.19 million every July 1st until 2035. What seemed like a clever financial move for the Mets has become an annual reminder of creative contract structuring gone wrong.
John Lackey’s Insurance Policy
Lackey’s Red Sox contract included a clever clause – if he missed significant time due to an elbow injury, the team would get an additional year at league minimum salary. When it happened, Lackey turned this seemingly team-friendly clause into leverage for a better deal with the Cardinals.
Roy Oswalt’s Heavy Equipment Bonus
When Oswalt won Game 6 of the 2005 NLCS, Astros owner Drayton McLane made good on his promise – delivering a brand new bulldozer to his ace pitcher. Sometimes the best contract bonuses aren’t about cash at all.
Manny’s Sushi Clause
When Manny Ramirez signed with Japan’s Koshien Tigers, he made sure unlimited sushi was part of the deal. Even in the twilight of his career, Manny never stopped being Manny.
Ray Caldwell’s Sobriety Penalty
The hurler led a very strange life, indeed. He had a drinking problem that was so severe that he was suspended from a Major League team and wound up pitching in another country under an assumed name for the rest of that year. Thanks to his incredible talents, though, he got more chances. The Indians were his last chance, and player/manager Tris Speaker added perhaps the most bizarre clause in baseball history. Caldwell’s contract actually allowed him to go out and drink heavily the night after a start. He could rest a day or two and then join the team. He was struck by lightning in his very first start under the new contract — and survived. That could drive a person to drink right there.
Barry Bonds’ Legal Protection
Bonds’ contract included a clause that would void the agreement if he was convicted of a crime. This was important given the BALCO investigation. In an era of increased scrutiny, even the game’s biggest stars had to protect themselves – and their teams – from legal complications. He got his money, but he’s still not in the Hall of Fame
Kevin Brown’s Private Fleet
The Dodgers agreed to provide Brown with 12 private jet trips home to Georgia each season. When you’re making top dollar, sometimes commercial flights just won’t cut it.
Curt Schilling’s Weighty Matters
In his 2007 Red Sox contract, Schilling had to maintain specific weight targets throughout the season, with regular weigh-ins determining his bonus eligibility. Sometimes the best motivation comes from your wallet.