Every team's biggest free-agent regret

October 23rd, 2021

A version of this story was first published in January 2019.

Free-agency season -- the "Hot Stove," if you will -- can be a dangerous game to play. Sure, that free-agent player looks shiny and enticing on the shelf, like he's the perfect fit for what ails your team, but remember: Every car starts losing value the minute you drive it off the lot.

No deal is truly a disaster, of course: Even the worst "busts" provide value for a team. But we'd all do some things differently if we had a chance to do them over again. With that in mind, we look at the most regrettable free-agent decision ever for each MLB team. Every franchise has some regrets. These ones still haunt fans of these teams today. Some of these are big deals gone wrong, while others are a different kind of regret, where a team let a star walk away only to watch him continue his dominance elsewhere.

Blue Jays: B.J. Ryan, five years, $47 million, 2005
Ryan had one great year for Toronto before Tommy John surgery essentially ended his career, and he spent the last year of this deal on the shelf.

Orioles: Albert Belle, five years, $65 million, 1999
Belle wasn't terrible for Baltimore when he played, but chronic hip problems forced him to retire two years into the deal.

Rays: Pat Burrell, two years, $16 million, 2009
Tampa Bay is famously hesitant to give big contracts, but the Rays thought spending for Burrell the year after he'd helped beat them in the World Series with Philadelphia would put them over the top. He ended up just hitting two homers in 24 games for them in 2010.

Red Sox: , five years, $95 million, 2014
Both the Red Sox and Sandoval came to regret this deal -- “If I had the opportunity to do it again, I wouldn’t do it," Sandoval said in 2019 -- as injuries and under-performance marred Kung Fu Panda's tenure in Boston.

Yankees: , seven years, $153 million, 2014
It's tough to remember that signing Ellsbury made sense at the time: The Yankees had missed the postseason, the Red Sox had just won the World Series and they were losing Robinson Canó in free agency anyway. So: Ellsbury. But what a disaster the deal turned out to be: He only took the field in four seasons for the Yanks and was a below-average hitter and fielder until injuries took over. Those injuries cost him the entire 2018 and '19 seasons, and he was released after the 2019 season before the contract was over. Here's the most damning Ellsbury stat with the Yanks: He didn't have a single postseason hit. (He was 0-for-10.)

Indians: Losing Manny Ramirez to the Red Sox, 2000
Cleveland wanted to keep Manny -- the Tribe offered him eight years, $136 million -- but Boston set the foundation of what it would be doing over the next decade by stealing him away.

Royals: Jose Guillen, three years, $36 million, 2008
Guillen was terrible for Kansas City, but he was even more of a problem off the field, criticizing the organization constantly and even getting in fights with fans. He is, uh, not missed.

Tigers: Mike Moore, three years, $10 million, 1992
Moore had been an All-Star and a World Series winner with Oakland just three years earlier. His career ERA in 86 starts for Detroit? 5.90.

Twins: Losing David Ortiz to the Red Sox, 2002
Technically speaking, Minnesota non-tendered Ortiz, a move that was a mistake then and has grown progressively more regrettable every year since. He subsequently signed with Boston, and you know the rest.

White Sox: Adam Dunn, four years, $56 million, 2011
Dunn hit .201 in his time with Chicago, which was low even for him, and even his 41-homer season came with 222 strikeouts.

Angels: Josh Hamilton, five years, $125 million, 2012
Hamilton was an inspiring story, and almost a World Series hero in 2011, but the Halos had to pay him more than $26 million after they released him.

Astros: Losing Randy Johnson to the D-backs, 1998
Johnson was always a non-waiver Trade Deadline day acquisition, but Houston could have kept him just as much as Arizona could have grabbed him. Three years later, the D-backs had won their World Series.

Athletics: Losing Catfish Hunter to the Yankees, 1974
There was no reason, really, for Oakland to lose Hunter; it was just a disagreement about a technicality in Hunter's contract. That led to an arbitration hearing that ended up voiding Hunter's contract and making him baseball's first free agent. (He of course then signed with the Yankees.)

Mariners: Carlos Silva, four years, $48 million, 2007
Silva wasn't particularly good before he signed with the Mariners, but with Seattle? 5-18, 6.81 ERA.

Rangers: Chan Ho Park, five years, $65 million
Park was thought of as an innings-eater before he came to Texas, but his 5.79 ERA with the Rangers probably made the fans wish he had pitched a lot less.

Braves: Melvin Upton Jr., five years, $72.3 million, 2013
B.J. Upton hit 28 homers in his walk year for the Rays … but Atlanta was ready to ship him out two years into his deal. By the end of the contract, he had a different name all together.

Marlins: John Burkett, two years, $7 million, 1995
Say what you will about the Marlins, but they're pretty good about not making terrible free-agent signings.

Mets: Losing , 2016
It's a special kind of pain to watch a guy finally figure out his swing right before he heads off to a division rival on a modest three-year deal and finishes second in the NL MVP Award vote.

Nationals: Matt Wieters, two years, $21 million, 2017
The Nats really needed a catcher when they signed this deal, and Wieters was coming off a year in which he made the All-Star team with Baltimore. But his power disappeared with Washington, and he posted a .658 OPS across two seasons.

Phillies: Losing Dave Stewart, 1986
Stewart had been run out of Texas and Philadelphia -- and almost went to Japan -- before the A's grabbed him in May 1986. Imagine how different the Phillies look the rest of that decade if they have peak Stewart?

Brewers: Jeffrey Hammonds, three years, $22.2 million, 2000
This deal came on the heels of Hammonds posting a .924 OPS with Colorado, and it's clear that teams were still not fully comprehending the Coors Field Effect.

Cardinals: Tino Martinez, three years, $21 million, 2002
Martinez was signed to be the Mark McGwire replacement, but he clearly missed New York. He was terrible in the 2002 postseason (going 2-for-25) and was eventually shipped to Tampa Bay before his contract was up.

Cubs: Losing Greg Maddux, 1992
Maddux had just won his first Cy Young Award with the Cubs the year before … so he just went out and won three more.

Pirates: Losing Barry Bonds, 1992
It's difficult to imagine any scenario Bonds would have stayed in Pittsburgh … but think of how different baseball history is if he had.

Reds: Eric Milton, three years, $25.5 million, 2005
Cincinnati was still learning about its new ballpark in 2005, and the Reds learned quickly: Fly-ball pitchers would struggle there.

D-backs: Russ Ortiz, four years, $33 million, 2004
Arizona got 28 starts out of Ortiz, who ended up with a 5-16 record with a 7.00 ERA.

Dodgers: Darren Dreifort, five years, $55 million, 2000
Dreifort pitched only 200 innings after Los Angeles gave him this deal, and he retired at the end of it.

Giants: Barry Zito, seven years, $126 million, 2006
Zito's ERA was more than a run higher with San Francisco than Oakland, though he did play for a couple of World Series winners. He wasn't worth it on a dollar-for-dollar level, but the fans still like him, so this isn't so bad as far as regrets go.

Padres: Oscar Gamble, six years, $2.8 million, 1978
Gamble's hair was glorious, of course … but he ended up playing just one year with San Diego, the worst year of his career.

Rockies: Mike Hampton, eight years, $121 million, 2001
Hampton famously said he chose Colorado because of the school system when he inked the deal, but he was already in Atlanta two years in.