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#3 Greg Maddux, Atlanta Braves (1993) 5 years-$28 million
Greg Maddux won the Cy Young Award in his last year with his old team, the Chicago Cubs. He was steadily improving every year and the Cy Young couldn’t have came at a better time. The 26-year old had instantly boosted his value and he retained the services of Scott Boras as his agent. The Cubs and Boras immediately went head-to-head with a battle of words. Each side accusing the other of not negotiating in good faith. Imagine that, a team having a hard time negotiating with Scott Boras.
It got messy, and along came the Atlanta Braves. Looking to add to a rotation that was already deep with the likes of John Smoltz, Tom Glavine and Steve Avery, the Braves went hard after Maddux. The Cubs decided to spend their money elsewhere with the additions of Jose Guzman, Dan Plesac and Candy Maldonado. All horrible moves when it comes down to losing their homegrown ace. Boras once again, frustrated a team to the point that they don’t make a smart baseball decision.
The Braves landed an ace and an unstoppable starting rotation was born. Maddux immediately rewarded the Braves with three straight Cy Young Awards and went 89-33 with a 2.14 ERA in the four years of the contract. He did so well with the team that they decided to have him stick around for six more years. Even though only one World Series title resulted in his time there, he was truly a steal at the price the Braves initially paid for his services.