Baseball players might spend most of their time perfecting their swing or fine-tuning their slider, but when it comes time to talk dollars, they wisely step aside and let the professionals do the talking. From record-breaking deals to savvy contract extensions, these stars had agents who earned their commissions.
Whether it was about maximizing value or securing an unimaginable perk, these players trusted their handler with the most important matters. And based on the results, they made the right call.
17. Eric Hosmer
Hosmer turned one good postseason run into a massive contract with San Diego. His agent knew precisely when to strike while the iron (and glove) was hot.
16. Jason Heyward
Heyward didn’t put up monster numbers, but he still landed one of the richest contracts of his era. That’s the kind of negotiating that deserves a trophy of its own.
15. Jacoby Ellsbury
Injuries may have limited his time on the field, but his contract with the Yankees never missed a payment. His agent pulled off a heist that’s still being whispered about in front offices.
14. Stephen Strasburg
When he opted out of a previous deal, some thought it was a risky move—then he signed an even bigger one. His agent had the Nationals right where they wanted them.
13. Albert Pujols
That ten-year deal with the Angels was massive, even if the back half didn’t exactly sparkle. Still, his agent secured generational wealth and then some.
12. Bobby Bonilla
The ultimate example of long-term planning, Bonilla hasn’t played since 2001 but still receives a paycheck every July 1. His agent didn’t just negotiate a contract—he created a national holiday.
11. Prince Fielder
Fielder’s career was cut short by injury, but his contract ensured he never had to worry. Credit goes to his agent for securing the nine-year deal with Texas.
10. Giancarlo Stanton
A 13-year contract worth over $300 million is not the kind of deal that comes along by accident. His agent secured a mountain of money and complete no-trade protection.
9. Robinson Canó
Jumping from the Yankees to the Mariners shocked everyone, but the money didn’t. His agent got him one of the biggest paydays in second-base history.
8. Joe Mauer
The hometown hero stayed in Minnesota, but not at a discount. His extension at the time made him the highest-paid catcher ever.
7. Manny Machado
Machado received his $300 million and later opted into a new $350 million extension. That’s how you keep winning at the negotiation table.
6. Joey Votto
Votto signed a massive extension with the Reds that paid him well into his late 30s. His agent understood the value of loyalty and how to capitalize on it.
5. Max Scherzer
Scherzer’s original Nationals deal had deferred money that still earns him interest, and then he followed it up with a short-term mega-deal from the Mets. His agent gave a masterclass in financial flexibility.
4. Corey Seager
Seager cashed in with Texas to the tune of $325 million. His agent knew that shortstop money was booming and got in at the perfect time.
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3. Alex Rodriguez
No one knew how to land a mega-deal like A-Rod and his agent. He didn’t just get one record-breaking contract—he got two.
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2. Shohei Ohtani
That $700 million contract might be deferred, but it remains the largest in sports history to date. His agent balanced marketing, endorsements, and flexibility like a pro.
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1. Scott Boras’s Entire Client List
From Bryce Harper to Gerrit Cole, Boras has a reputation for squeezing every possible dollar out of every team. If there’s one guy who can do the heavy lifting, it’s the man behind half of baseball’s richest contracts.
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