The best (and worst) free agent signings in MLB history ...Middle East

Bradford DoolittleApr 10, 2026, 07:00 AM ET

Multiple Authors

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.

Hunter’s case wasn’t a true precedent for the kind of free agency we know today, but it was a steppingstone that galvanized the players who had little by little been winning new rights under Miller for years. When they saw teams dive headlong into a feeding frenzy, trying to secure Hunter’s services, they saw proof of concept of what free agency could mean for them.

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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.

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.

Jump to:

1-25 | … 8,330-8,340 | How we ranked them

Worth the money and then some: The top 25

One system’s take on the 25 most impactful free agent signings of the last half-century.

1. Barry Bonds (2,563.6 points)

First year: 1993 | Team: GiantsInitial terms: 6 years, $43.8 million | bWAR: 109.1

The Bonds deal, which by the definitions used in this study has a 14-year duration due to extensions, laps the field in terms of its on-field impact. If the only bWAR Bonds accrued during his career came from these seasons, his total of 109.1 would still rank 23rd on the all-time list. For me, the most remarkable thing about it is that the Giants were coming off an uninspiring 72-90 season when they made this splash.

2. Greg Maddux (1,173.6 points)

First year: 1993 | Team: BravesInitial terms: 5 years, $28.0 million | bWAR: 66.1

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.

3. David Ortiz (818.3 points)

First year: 2003 | Team: Red SoxInitial terms: 1 year, $1.3 million | bWAR: 34.2

You can quibble whether this one belongs, but I’m keeping it. Ortiz wasn’t a free agent because he reached any service time requirement, but because the Twins released him, at age 26, even though he was coming off his best season (20 homers, 120 OPS+). Papi finished fifth in AL MVP voting in his first Boston season and kept re-signing and extending until he finally reentered free agency after the 2011 season. By then, he was a legend. And, of course, he never left the Red Sox.

4. Larry Walker (780.3 points)

First year: 1995 | Team: RockiesInitial terms: 4 years, $22.5 million | bWAR: 48.3

Walker ended up spending a decade with the Rockies, putting up video game numbers while building a résumé that landed him in the Hall of Fame. Say what you will about playing in Denver — and Walker hit .381 at Coors Field for his career — but the numbers are ridiculous. During one six-year stretch, which covered his seasons from age 30 to 35, Walker hit a composite .353 and averaged 6.0 bWAR.

5. Randy Johnson (777.0 points)

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First year: 1999 | Team: DiamondbacksInitial terms: 4 years, $52.5 million plus option | bWAR: 46.6

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.

6. Craig Biggio (663.2 points)

First year: 1996 | Team: AstrosInitial terms: 4 years, $22.4 million | bWAR: 37.9

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.

7. Rickey Henderson (632.4 points)

First year: 1990 | Team: AthleticsInitial terms: 4 years, $12.0 million | bWAR: 24.7

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.

8. Adrian Beltré (631.3 points)

First year: 2011 | Team: RangersInitial terms: 5 years, $80 million | bWAR: 41.3

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.

9. Manny Ramirez (579.4 points)

First year: 2001 | Team: Red SoxInitial terms: 8 years, $160 million | bWAR: 33.2

Ramirez made it 7½ years through this deal before being traded to the Dodgers in 2008. It was always an adventure — “Manny being Manny” — but in the history of a franchise that’s featured many of baseball’s all-time best hitters, Ramirez ranks right with them. In terms of OPS+, the order goes: Ted Williams, Tris Speaker, Jimmie Foxx, Manny, Ortiz and Wade Boggs. Ramirez was often not very serious, but the man could seriously hit.

10. Bobby Grich (523.1 points)

First year: 1977 | Team: AngelsInitial terms: 5 years, $1.5 million | bWAR: 33.2

If we had better defensive metrics in the 1970s, if we understood positional value and the importance of on-base ability more back then, and the WAR framework had been in place, maybe Grich wouldn’t have become one of the most criminally underrated players in history. He was one of a number of high-profile free agents the Angels signed when owner Gene Autry was making his big push for a title, using the new avenue of free agency to fuel his pursuit. In Grich, he landed a player who isn’t in Cooperstown but should be.

11. Rich Gossage (520.7 points)

First year: 1978 | Team: YankeesInitial terms: 6 years, $3.6 million | bWAR: 18.6

Didn’t you hear? It’s a bad idea to sign relief pitchers to long contracts. There are still exceptions to that basic principle of free agency and, anyway, Gossage’s career was very different than that of the leading firemen of today. In his first Yankees season, Gossage led the AL with 27 saves and threw 134⅓ innings — more than any member of the 2025 Dodgers’ starting rotation aside from Yoshinobu Yamamoto. (Even with all his success in New York, Royals fans think of Gossage fondly, too, for giving up some of George Brett’s most memorable home runs.)

12. Carlos Beltrán (509.3 points)

First year: 2005 | Team: MetsInitial terms: 7 years, $119 million | bWAR: 31.1

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.

13. Tony Phillips (481.7 points)

First year: 1990 | Team: TigersInitial terms: 3 years, $4 million | bWAR: 25.3

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.

14. Aaron Judge (479.1 points)

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First year: 2023 | Team: YankeesInitial terms: 9 years, $400 million | bWAR: 25.1

Two active contracts cracked the top 25 — here’s the first. Let’s flash back to those fleeting hours when we thought Judge had signed with the Giants when he reached free agency. Now we know that close call is the flip side of what Bonds says about his free agency — that he very nearly landed with the Yankees. Judge has a 207 OPS+ and 151 homers since signing the deal. And that includes this season, which is just getting started. This deal lands at No. 14 now, but it’s going to keep climbing for years to come.

15. Jamie Moyer (462.1 points)

First year: 1997 | Team: MarinersInitial terms: 2 years, $3.7 million | bWAR: 24.7

I love this one. It was not a big deal when Moyer re-signed with Seattle as an older free agent after the 1996 season. He had already been with the Mariners for a half-season, having been traded from Boston. While his initial stint with Seattle was solid, Moyer reached free agency at age 33 with a 72-79 career record and a 98 ERA+. It would be another 15 years before he finally retired. Moyer didn’t reenter free agency after this deal until the 2002 season. (Then he re-signed with the Mariners.) But during the duration of this pact, he went 92-46 with a 117 ERA+ and had two top-10 Cy Young finishes.

16. Max Scherzer (452.5 points)

First year: 2015 | Team: NationalsInitial terms: 7 years, $210 million | bWAR: 40.3

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.

17. Reggie Jackson (441.5 points)

First year: 1977 | Team: YankeesInitial terms: 5 years, $3.5 million | bWAR: 17.2

The first headline-dominating free agent signing. Reggie, to the Big Apple, where he joined George Steinbrenner and Billy Martin to become the straw that stirred the drink. These were Jackson’s age-31 to age-35 seasons, and while he hit 144 homers for New York (plus another 12 in the postseason), he was a better player during his younger days with the Oakland Athletics. Yet he is cemented in our collective baseball memory as wearing Yankee pinstripes, and it is indeed a classic interlocking “NY” cap on his Cooperstown plaque.

18. Edwin Encarnación (435.7 points)

First year: 2011 | Team: Blue JaysInitial terms: 1 year, $2.5 million plus option | bWAR: 22.5

This is another one that belongs because of its strange shape. Encarnacion first joined the Jays as part of the return for Scott Rolen, who was shipped to Cincinnati prior to the 2010 campaign. He then was designated for assignment by Toronto during the season, outrighted to the minors, and, after the season, claimed by the Athletics on waivers. But Oakland non-tendered him less than a month later, making Encarnacion a free agent. The Blue Jays tried again with this pact. Encarnacion wound up playing the next six seasons in Toronto, mashing 193 homers and becoming a central part of one of baseball’s most feared lineups.

19. Shohei Ohtani (435.5 points)

First year: 2024 | Team: DodgersInitial terms: 10 years, $700 million | bWAR: 16.9

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.

20. Dave Winfield (433.3 points)

First year: 1981 | Team: YankeesInitial terms: 10 years, $23 million | bWAR: 27.1

If the system awarded bonus points for enduring insults from your own team’s owner, Winfield might rank near the top. Despite, or perhaps because of, George Steinbrenner’s incessant bashing of Winfield, his play with New York was nevertheless high level. Winfield averaged 25 homers and 101 RBIs during the first eight years of the deal, put up an OPS+ of 135, won five Gold Gloves and made the AL All-Star team in each campaign.

21. Vladimir Guerrero Sr. (427.1 points)

First year: 2004 | Team: AngelsInitial terms: 5 years, $70 million | bWAR: 22.8

Perhaps the only unfortunate part of the 14-year extension Vladimir Guerrero Jr. signed last year with the Blue Jays is it means he’ll likely never have a chance to join his father on this list. Vladdy Sr.’s play tailed off toward the end of his stay with the Angels, but during his first five seasons with the Halos, he hit .323/.387/.557 while averaging 31.6 homers and 113.2 RBIs. After the first season of this deal, Guerrero won his only AL MVP award. The Angels’ history of free agent splashes is long, complicated and widely disparate in its outcomes, but this one was a jewel.

22. Tom Candiotti (423.8 points)

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First year: 1986 | Team: ClevelandInitial terms: Minor league contract | bWAR: 22.5

I probably should have filtered this one out, but I can’t because I love it so much — and he was, in fact, a free agent. Candiotti was all but a washout by the time he latched on with Cleveland. After languishing in the Milwaukee organization for several seasons, he was set loose after the 1985 season, when he didn’t pitch at all in the majors and went 9-13 in Triple-A. He was already 29 years old and owned a career big league mark of 6-6, hence the initial minor league deal with the Indians. By the time Candiotti was traded to Toronto during the 1991 season, he’d won 78 games for some not-great Cleveland teams with a 119 ERA+ and 4.3 bWAR per season.

23. Paul Molitor (422.8 points)

First year: 1988 | Team: BrewersInitial terms: 2 years, $3.5 million | bWAR: 24.2

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.

24. Roger Clemens (416.4 points)

First year: 1997 | Team: Blue JaysInitial terms: 3 years, $24.5 million | bWAR: 20.2

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.

25. Roberto Alomar (414.2 points)

First year: 1999 | Team: ClevelandInitial terms: 4 years, $32 million plus option | bWAR: 20.3

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.

Signings that didn’t work out so well: The bottom 11

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.

8,330. Kris Bryant (minus-226.0 points)

First year: 2022 | Team: RockiesInitial terms: 7 years, $182 million | bWAR: Minus-1.6

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.

8,331. Jaime Navarro (minus-232.0 points)

First year: 1997 | Team: White SoxInitial terms: 4 years, $20 million | bWAR: Minus-3.8

Same city, very different results. In two seasons with the Cubs, Navarro went 29-18 with a 6.0 bWAR. He signed with the White Sox and on the South Side went 35-43 with minus-3.8 bWAR. Ouch.

8,332. Jeff Suppan (minus-232.7 points)

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First year: 2007 | Team: BrewersInitial terms: 4 years, $42 million | bWAR: Minus-0.9

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.

8,333. Jason Heyward (minus-240.6 points)

First year: 2016 | Team: CubsInitial terms: 8 years, $184 million | bWAR: 9.1

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.

8,334. Albert Pujols (minus-252.6 points)

First year: 2012 | Team: AngelsInitial terms: 10 years, $240 million | bWAR: 12.5

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.

8,335. Anthony Rendon (minus-275.5 points)

First year: 2020 | Team: AngelsInitial terms: 7 years, $245 million | bWAR: 3.9

And this one was even worse, even with Rendon mercifully calling it quits.

8,336. Jordan Zimmermann (minus-279.2 points)

First year: 2016 | Team: TigersInitial terms: 5 years, $110 million | bWAR: 1.9

Like Suppan, Zimmermann 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.

8,337. Patrick Corbin (minus-302.0 points)

First year: 2019 | Team: NationalsInitial terms: 6 years, $140 million | bWAR: 2.6

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.

8,338. Stephen Strasburg (minus-302.8 points)

First year: 2020 | Team: NationalsInitial terms: 7 years, $245 million | bWAR: Minus-0.4

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.

8,339. Chris Davis (minus-360.9 points)

First year: 2016 | Team: OriolesInitial terms: 7 years, $161 million | bWAR: Minus-2.8

It all seemed fine when the Orioles re-signed Davis, their own free agent, who’d had AL-leading homer totals of 53 and 47 in two of the previous three seasons. But this contract went from questionable to terrifying with each season of Davis’ plummeting OPS, which was .923 during his platform season. Then: .792, .732, .539, .601, .337, retirement.

8,340. Barry Zito (minus-386.9 points)

First year: 2007 | Team: GiantsInitial terms: 7 years, $126 million | bWAR: 1.7

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.

Methodology: How we compiled free agency points

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:

1. Aggregate performance during the deal, as measured by bWAR

2. Average performance during the deal

3. Win probability added during the deal

4. Championship win probability added during the deal

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.

Performance data, free agent lists and raw salary data were taken from baseball-reference.com. Cot’s Contracts from Baseball Prospectus was used to obtain terms for any free agent deal signed since 1991. Terms for contracts before that were cobbled together from archival news reports. I tried to note contract options where appropriate, but some were likely missed.

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