Last Updated: October 20th, 2026 by Matthew Brown
Free agency is one of the great innovations that baseball has made. It not only became a major part of the sport, but also a major part of all the major sports in the United States of America. Even though it gave more freedom to athletes, it also put a lot of pressure on front offices to make sure that they were spending their budgets wisely.
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Here we have some of the free agents in history that those respective front offices wish they hadn't signed on the dotted line.
Jeffrey Hammonds’ Brewers Bust
One of the more underrated, exciting teams in baseball during this time, the Milwaukee Brewers thought they had a perennial All-Star on their hands when they signed Jeffrey Hammonds following his All-Star season in 2000.
The problem was that he had that jump in production because that was his first and only season with the Colorado Rockies. Coors Field gave him a boost in the stat sheet and his wallet, but Hammonds couldn't give a boost to the Brewers' lineup.
Tino Martinez’s Cardinals Disappointment
There was almost no doubt from the St. Louis front office that they were making a good investment in Tino Martinez. He had been a part of the recent Yankees dynasty as a valuable piece, so the Cardinals were willing to look past the fact that he was about to be 34 years old when he played his first season with them.
His numbers dropped to league average, and he lasted just two years.
Cubs Let Greg Maddux Slip Away
Now we look at the other side of teams in free agency. The teams that have great players on their payroll, but watch them walk away to the highest bidder. Greg Maddux had just won his first of what would be four straight Cy Young Awards.
Of course, the Cubs couldn't foresee those next few Cy Youngs, but they didn't end up giving him the best-looking contract, and the Atlanta Braves would be able to put together one of the greatest rotations in history.
Pirates Lose Barry Bonds
Many will say that Barry Bonds was a Hall of Famer before he even put on a Giants jersey. He won two MVPs in three seasons before taking the bigger contract to go to San Francisco.
The Pittsburgh Pirates are a smaller-market team and weren't willing to spend so much money on one player. The thing is, that one player is considered the greatest slugger of all time.
Eric Milton’s Cincinnati Disaster
In the early 2000s, Eric Milton was a respectable starting pitcher who could help in the middle part of a rotation. His numbers weren't eye-popping, but anything under a 5.00 ERA was useful in that era.
Unfortunately for him and the Reds, his ERA jumped to 6.47 in his first season in Cincinnati thanks to the hitter-friendly ballpark he was pitching in.
Diamondbacks’ Russ Ortiz Mistake
I thought Russ Ortiz was underrated back when he was winning 21 games for the Atlanta Braves in 2003. That actually followed a solid five seasons in San Francisco. The Diamondbacks thought they could get a little bit of that effectiveness in Arizona.
The exact opposite happened, as Ortiz had a 7.00 ERA over 28 starts. He never really found his groove after that.
Dodgers’ Darren Dreifort Debacle
The Dodgers have had a great history of developing players, and one of their best eras in doing so was the 1990s. They had five consecutive Rookie of the Year Award winners in that decade, and while Darren Dreifort wasn't one of them, they thought they had a future star in him.
A five-year, $55 million deal in 2000 didn't lead to much, as injuries derailed the rest of his short career.
Barry Zito’s Giants Contract
The Moneyball A's made a handful of stars who signed big contracts to go elsewhere. Barry Zito was one of the most anticipated signings as the Giants were able to ink him to a massive seven-year deal.
That ended up becoming a massive hole as Zito never found his footing in San Francisco. He had a rough 63-80 record with a 4.62 ERA over the full length of the contract.
Mike Hampton’s Rocky Mountain Low
This one is a little more puzzling. Mike Hampton was a 20-game winner and an All-Star with World Series experience when the Rockies signed him to the largest contract in baseball history at the time.
I'm guessing they thought his added value with the bat would make him look like Babe Ruth in Denver. That didn't quite end up happening, and they traded him two years into his eight-year contract.
Oscar Gamble’s Short-Lived Padres Stint
During the earlier days of free agency, Oscar Gamble signed a six-year deal to try to be a major piece for a young San Diego Padres franchise. Even with a pretty good year in 1978, the Padres weren't satisfied and traded him in the offseason.
Expectations and reality are always different, but sometimes being patient with results could be a better reaction.
