Bradford DoolittleApr 10, 2026, 07:00 AM ETCloseMLB writer and analyst for ESPN.com Former NBA writer and analyst for ESPN.com Been with ESPN since 2013Multiple Authors
Signings that didn’t work out so well: The bottom 11
Baseball free agency recently celebrated its 50th anniversary, insofar as a contractual classification can celebrate something.
There’s no apparent consensus on who the first free agent actually was, or when that player became a free agent, but for me, it’s pitcher Andy Messersmith and the date was March 16, 1976. I bet you forgot to send a card.
Some refer to Catfish Hunter as the first free agent, two years prior to Messersmith, and while it’s true that Hunter won free agency on Dec. 16, 1974, and subsequently signed a then-massive deal with the Yankees (five years, $3.2 million), that was a bit of a fluke. It was a result of some deft legal maneuvering by Hunter and Marvin Miller’s players’ union, all related to a clause in Hunter’s contract with Charlie Finley’s Athletics.
So mark that on your calendar — Messersmith, March 16 — right between the Ides of March and St. Patrick’s Day. Anyway, we’re a little belated with our revelry, but it’s not too late: Messersmith ultimately signed the first free agent deal, a three-year, $1 million contract with the Braves, on April 10, 1976 — exactly 50 years ago today.
In honor of this, we’re going to list the 25 most successful free agent deals that have followed in Messersmith’s wake — and some of the ones that haven’t quite worked out. There are 8,340 free agent pacts we evaluated for the rankings, a long list that began with Messersmith, not to mention those who lit the path for him.
It’s hard to imagine it now, but when Maddux moved from the Cubs to the Braves, it was only the second-biggest move of the 1992-93 hot stove season, behind Bonds. Maddux wound up spending 11 seasons in Atlanta, during which he went 194-88 with a 163 ERA+ and won three Cy Young Awards.
Biggio enjoyed that most precious of baseball career types, that of the one-team Hall of Famer. He never played for anyone but the Astros, but he did reach free agency after the 1995 season. He re-signed with the Astros, and that deal kept getting extended until it eventually reached 11 years. It’s impossible to picture Biggio with another franchise.
According to my algorithm for flagging free agent deals, Henderson signed seven of them during his career, three with the Athletics. This was the most successful of those pacts, beginning with his epic 1990 season, when Henderson put up 9.9 bWAR and won his only MVP Award. He didn’t quite make it through all four seasons of the deal, as he was dealt to the Blue Jays in the midst of Toronto’s title-winning 1993 campaign.
The Rangers were Beltre’s fourth team and he was already 31 years old when he signed with Texas. Yet those years were so successful he wound up spending his final eight campaigns with the Rangers, and it’s their cap featured on his Hall of Fame plaque. The dogma now is that signing post-30 free agents to long-term deals is risky. (And it is.) But Beltre was better during his final eight years than he was during his first 13 — and he was really good in the first 13.
Beltran is Cooperstown-bound this July and will don a Mets cap on his Hall of Fame plaque. Not long after his induction, Beltran will have his No. 15 retired by the club. These are strong indicators that his big contract with the Mets worked out to the mutual satisfaction of both parties. Beltran’s best seasons by bWAR (2006 and 2008) came during his Mets tenure.
Here’s a sneaky one! Phillips wasn’t just really good during what became a five-year stay with the Tigers, he wasn’t super expensive, boosting the economic efficiency component in our points system. During those five years, Phillips’ age-31 to age-35 seasons, he averaged 5.1 bWAR, posted a composite .395 OBP and averaged more than 100 runs scored — all while playing capably all over the field on defense.
Scherzer won two Cy Young Awards for the Nationals, giving him three in all, and helped Washington win the 2019 World Series. He averaged 6.0 bWAR and had an ERA+ of 152 before being dealt to the Dodgers in the last year of the contract (2021). Then, for L.A., he went 7-0 with 1.98 ERA and landed yet another massive deal, this one with the Mets.
It’s a stunning, ridiculous contract that a little over two seasons in already looks like a bargain. This deal might not catch Bonds, but there’s a long way to go.
Molitor was an established star and beloved figure in Milwaukee when he first reached free agency after the 1987 season. He stayed put and eventually signed an extension that kept him with the Brewers through the 1992 season, his age-35 campaign. As good as Molitor was, he amazingly put up even better numbers after his second free agent deal, signed with the Blue Jays, with whom he won a World Series. But this one cemented him forever in the hearts of Brewers fans.
Clemens was traded to the Yankees before the third season of this deal (at his request), so his point total is actually based on just two seasons. They weren’t bad: Two Cy Youngs, a 41-13 record, 20.2 bWAR and back-to-back pitching triple crowns. Clemens — again, based on two seasons — ranks seventh on the Blue Jays’ career pitching bWAR leaderboard.
Alomar was the best second baseman in the game and a likely Hall of Famer when he signed this contract before his age-31 season. Then he somehow got better, averaging 6.8 bWAR (including the two best single-season totals of his career), won three Gold Gloves and put up a 134 OPS+. That secures the last spot in our top 25, even though Alomar was traded to the Mets before the fourth season of the deal.
Out of 8,340 free-agent deals we rated with our points system, these ended up at the bottom. We went to 11 to get in the lone active contract in this sector of the rankings. Active, as in it can still get worse.
Even if Bryant had not been beset with horrific-sounding back issues, this deal was never a good idea. But the back trouble nudges this signing toward the realm of tragedy.
Always a control pitcher whose performance seemed consistent enough within a narrow band, the Brewers signed him just as things were heading south. He had an 84 ERA+ during his time in Milwaukee, posting a minus-0.9 bWAR.
Hey, if you like the Cubs and want to argue that Heyward’s defense and his pep talk during the rain delay in Game 7 of the 2016 World Series renders the efficiency of this contract moot, I won’t try to talk you out of it. Flags fly forever.
Pujols never stopped being a class act. and it’s not his fault Angels owner Arte Moreno tends to lose his cool during free agency at times. But this was not a good contract for the Angels.
Like Suppan, Zimmerman seemed to be both durable and consistent at the time the Tigers signed him. In seven years for the Nationals, he had a 3.32 ERA. The following five years, on the Tigers’ dime, that number was 5.63.
In retrospect, Corbin really had only one high-level season under his belt when the Nationals signed him. And his first season for Washington was terrific — 14-7, 138 ERA+, 5.1 bWAR — and he helped the Nats win it all. So he has that flags thing going for him as well. But after that magical season, Corbin’s composite bWAR over the next five seasons was minus-2.3.
It was a supremely bad contract given at the wrong time to a superstar pitcher coming off one of his best seasons. Pitching injuries suck. Strasburg won a lone game after signing this deal.
Zito put up a 30.6 bWAR during eight seasons for the A’s, earning him this huge payday on the other side of the bay. He pitched all seven seasons of it for San Francisco, going 63-80 with an ERA+ of 87.
Some ground rules on how these rankings were compiled. Free agent contracts — and any extensions to those contracts — were evaluated for player performance under the duration of that deal, and its economic efficiency. Points were awarded for:
5. bWAR produced above or below expectation, based on the player’s salary and the average cost of one win in the study’s database
Points in each category were determined by taking the z-score of each result times 10, and the output can be positive or negative. Triple weight was given to categories 4 and 5. All salary figures were indexed to the current average MLB salary to account for the changing economic landscape of the last 50 years.
The duration of a deal is defined as the time between the first year of the contract and the year in which the player changed teams, retired, was released or re-entered free agency. Thus if a player was awarded an extension, or simply re-signed before entering free agency, his free agent contract duration includes those additional seasons.
For example, Barry Bonds’ original deal with the Giants, which began in 1993, was for six years. But due to subsequent extensions, he did not reenter free agency until after the 2006 season. Thus, the duration of Bonds’ initial free agent deal is measured at 14 seasons. His final season, 2007, is considered a separate contract even though he re-signed with the Giants because he was in fact awarded free agency.
But it was Messersmith and all-but-retired fellow pitcher Dave McNally who finally challenged — and defeated — baseball’s reserve clause, which bound players to their teams. It ostensibly fell on Dec. 23, 1975, in a historic decision by arbitrator Peter Seitz. That decision was upheld on appeal on Feb. 3, 1976, clearing the way for Messersmith and McNally to be granted free agency on March 16. But McNally was just helping out the players; he had no intention of continuing his career. Thus it was Messersmith, who moved from the Dodgers to the Braves, who was at the vanguard of what we now know as free agency and which was formalized in the next CBA, agreed to on July 12, 1976.
This signing worked out pretty well. If you just focus on the four guaranteed seasons of the original pact, Johnson won NL Cy Young Awards in all of them. His lowest strikeout total during those years was 334. He averaged 9.5 bWAR, 20.4 wins and 354 whiffs. It’s a four-year run as good as any pitcher has ever had. All of this with the Diamondbacks, who when they signed the Big Unit were coming off their 97-loss inaugural season as a franchise. Johnson would be named co-MVP of Arizona’s 2001 World Series victory over the Yankees.