Dating back to the late 1990s, there have been 76 instances of MLB players signing a contract with a minimum value of $100 million. Two more were added to that list when Bryce Harper and Manny Machado landed lucrative deals last year, and this offseason should see that number rise.
Kevin Brown holds the unique distinction of being the first MLB player to sign such a contract to that extent. The then-33-year-old made history in December 1998 when he inked a seven-year, $105 million commitment with the Los Angeles Dodgers.
The signing was criticized at the time, as the Dodgers had essentially bid against themselves in negotiations. Moreover, Brown was approaching his mid-30s with plenty of wear-and-tear on his arm.
Former Dodgers general manager Kevin Malone reflected on the signing of Brown and revealed that he has no regrets dishing out that kind of contract at the time, per Gabriel Baumgaertner of Sports Illustrated:
“Mike Piazza had just signed for $91 million in New York and Mo Vaughn signed for $80 million in Anaheim,” Malone says. “I didn’t think it was a stretch to break through this arbitrary $100 million glass ceiling. We wanted his production, his intensity and his ability to make pitchers around him better. We pushed it to the limit because we felt it was worth it.”
“I feel like I was ahead of the curve. I knew what it took to take care of my team and all I regret is that we didn’t win a championship.”
“If other teams had the resources, they’d have made the deal I made. A bunch of people came up to me after the deal and said ‘I would have done the same thing.’”
Coming off back-to-back seasons without a postseason appearance, Malone clearly wanted to make a splash in free agency and propel the Dodgers back into October.
Despite the many doubts that he would produce at an elite level, Brown still enjoyed a solid five-year stint with the Dodgers.
He was selected to the All-Star Game twice from 1999-2003, accumulating a 58-32 record with a 2.83 ERA, 3.16 FIP and 1.10 WHIP in 872.2 innings pitched. Brown was traded to the New York Yankees after the 2003 season and retired a mere two years later when his contract expired.
