The best and worst MLB free-agent signings of the past decade


From 2012 to 2021, MLB teams spent a collective $16.66 billion on free agency. Thirty-one players received deals valued at $100-plus million and another 55 received $50 million or more. Some of those deals paid huge dividends — Max Scherzer‘s seven-year contract with the Nationals was the best of the big-money signings. Many of those deals did not come close to working out as teams hoped.

Of the 10 free agents who received the biggest contract each year, two won a World Series — David Price with the Red Sox in 2018 and Scherzer in 2019. Those 10 players have played, so far, 43 seasons with the team that signed them — and made just 13 playoff appearances, or roughly the same one-in-three odds that would happen randomly.

An examination of the past decade of free agency can help point to why the sport is where it is right now, with the owners having locked out the players and little momentum being made in creating a new collective bargaining agreement. The players are upset as their percentage of revenue has declined in recent years. That’s true. It’s also true that many of the top free agents simply haven’t performed and front offices are less willing to sign free agents with the same approach as five or 10 years ago.

As we wait for baseball activities to resume, let’s take a capsule look at each year of free agency (contract information from the invaluable Cot’s Contracts site).


Biggest contract: Albert Pujols, Angels (10 years, $240 million)

It’s easy to forget the Angels were a powerhouse franchise when owner Arte Moreno, who had lost out on big free agents in prior years, signed Pujols to what at the time was the third-largest contract in history, behind only Alex Rodriguez’s two deals. While the Angels had missed the playoffs in 2010 and 2011, they had made the postseason six times over the previous 10 seasons. They had drawn three million fans every season since 2003 — and had outdrawn the Dodgers in 2011. Moreno wanted to make the biggest of splashes, and the Angels outbid the Cardinals, Cubs and, believe or not, the Marlins (who reportedly offered more total dollars, but wouldn’t include a no-trade clause).

Of note: While Pujols had led the Cardinals to the World Series title in 2011, he was coming off his worst season, with his first sub-.300 batting average and lowest OPS. At his introductory press conference, the Angels didn’t seem concerned the deal would take Pujols through his age-41 season. Pujols talked about playing until he was 45. Moreno talked about how the Angels “have done very well financially and have no debt.” Indeed, maybe the Angels still did OK with his deal, despite making the playoffs just once during its lifetime: They continued drawing three million fans a season until COVID hit in 2020 and, according to Forbes, the value of the Angels has increased from $656 million in 2012 to $2.025 billion.

Roll of the dice: Jose Reyes, Marlins (six years, $106 million)

This was the year the Marlins were moving into their new stadium and then-owner Jeffrey Loria decided to buy some free agents, signing Reyes, Mark Buehrle and Heath Bell. Reyes was coming off a batting title with the Mets in 2011, but that .337 average was 45 points above his career mark. Reyes regressed to his career norms in 2012 — .287/.347/.433 — as the Marlins actually declined from 72-90 to 69-93. Loria decided he didn’t like spending money after all and traded away the three free agents he had signed.

Best bargain: Bartolo Colon, A’s (one year, $2 million)

After years of injuries, Colon had gone 8-10 with a 4.00 ERA for the Yankees in 2011, but there was little interest. Who knew he still had 86 more wins in him? He went 10-9 with a 3.43 ERA for the A’s as they surprisingly won the AL West, but he tested positive for PEDs in August and missed the postseason.


Biggest contract: Zack Greinke, Dodgers (six years, $147 million)

Greinke’s deal was the second-biggest ever for a pitcher at the time, trailing only CC Sabathia’s $161 million contract with the Yankees, and he didn’t disappoint, going 51-15 with a 2.30 ERA in three years with the Dodgers, before exercising an opt-out clause and signing with the Diamondbacks.

Roll of the dice: Josh Hamilton, Angels (five years, $125 million)

Hamilton had been the 2010 AL MVP and bashed 43 home runs and drove in 128 runs for the Rangers in 2012, but there were indicators that this might be a risky move even as the Angels dreamed of lining up Hamilton, Pujols and Mike Trout. Hamilton had hit .368/.420/.764 through the first two months of 2012, but just .245/.322/.487 in the final four and his strikeout rate had increased significantly from previous seasons. He was entering his age-32 season and the Angels were removing him from his comfort level with the Rangers, where he had successfully dealt with his addiction history.

It didn’t work out. Hamilton, in fact, would last just two seasons with the Angels. Always an aggressive swinger, he was so talented and his hand-eye coordination so good that he could get away with his poor approach. By the time he signed with the Angels, that was no longer the case. Then came the injuries and he was out of the majors just three years after signing.

Best bargain: David Ortiz, Red Sox (two years, $26 million)

Coming off a one-year deal in 2012, when he posted a 1.026 OPS in 90 games, Ortiz re-signed on what would be another sweetheart deal for the Red Sox. In 2013, at age 37, Ortiz hit .309/.395/.564 with 30 home runs and then hit .353/.500/.706 in the postseason, winning World Series MVP honors as he hit .688. The Cardinals finally gave up on pitching to him and walked him four times in Game 6.


Biggest contract: Robinson Cano, Mariners (10 years, $240 million)

This certainly was one of the most shocking contracts of the past 10 years — not just that the Mariners were able to buy him away from the Yankees, but that they easily trumped the Yankees’ reported seven-year, $175 million offer. Cano said he never felt as if the Yankees really wanted him back. “I didn’t feel respect,” he said when introduced in Seattle. “I didn’t get respect from them and I didn’t see any effort.”

Remarkably, the deal wasn’t a disaster for the Mariners. Cano gave them five good seasons, albeit with a PED suspension in the fifth year, and then Jerry Dipoto (who wasn’t general manager for the original deal, that was Jack Zduriencik) was somehow able foist Cano and much of his remaining contract on the Mets in a deal that brought over prospect Jarred Kelenic. Yes, the Mets still owe Cano $40.5 million over the next two seasons. Those 10-year contracts … buyer beware.

Roll of the dice: Jacoby Ellsbury, Yankees (seven years, $153 million)

Although the Yankees let Cano walk, they were still aggressive in free agency — signing not only Ellsbury, but Brian McCann and Carlos Beltran for a combined $283 million. Ellsbury was a huge risk after averaging 96 games per season over his final four years in Boston — and sure enough, he would play just four seasons with the Yankees, never coming close to his magical 2011 season when he finished second in the MVP voting.

Best bargain: Nelson Cruz, Orioles (one year, $8 million)

Cruz averaged 27 home runs for the Rangers from 2009 through 2013, but had been suspended 50 games in 2013 for his involvement in the Biogenesis case. Cruz rejected the Rangers’ qualifying offer, found little interest in his services, and finally settled for a one-year deal from the Orioles. He led the AL with 40 home runs as the Orioles won the AL East and then parlayed his big season into a four-year, $57 million deal with Seattle — one that was criticized at the time, but he would lead the majors in home runs over the four seasons.


Biggest contract: Max Scherzer, Nationals (seven years, $210 million)

Not all long-term, megadeal contracts for pitchers are fated to end up with a broken-down hurler eating up too much of a team’s payroll. This one is on the short list of greatest free-agent signings of all time. Scherzer was great all seven years of the deal, going 99-47 with a 2.75 ERA, with two Cy Young Awards and top-five finishes four other times. He helped the Nationals win the World Series in 2019 and then, in his final year of the deal in 2021 and the Nationals scuffling, was traded to the Dodgers and brought the Nationals a nice return of prospects. From the Nationals’ financial perspective, the deal looks even better as the unusual structure of the deferred money in the contract meant MLB valued the contract at about $185 million in present-day money.

Roll of the dice: Pablo Sandoval (five years, $95 million) and Hanley Ramirez (four years, $88 million), Red Sox

After winning the World Series in 2013, the Red Sox collapsed to 71-91 in 2014, so they were looking for some instant talent infusion via free agency. They gambled on two players with red flags in their backgrounds: Sandoval with his weight and Ramirez with injuries and inconsistent production. Making Ramirez’s signing even more of a risk, the Red Sox planned to move him from shortstop to left field.

The two moves would cost Ben Cherington his job as Red Sox GM. Ramirez couldn’t play left field. Sandoval didn’t hit. The two combined for minus-0.4 WAR with the Red Sox, who would end up eating a large chunk of Sandoval’s salary after releasing him midway through the deal.

Best bargain: Edinson Volquez, Royals (two years, $20 million)

After losing the 2014 World Series to the Giants, the Royals did what small-market teams rarely do: They spent money. They didn’t go big, but they signed Volquez, Kendrys Morales, Alex Rios, Luke Hochevar and Chris Young (and would trade for Ben Zobrist and Johnny Cueto during the season). Volquez would be the key signing, as he went 13-9 with a 3.55 ERA and led the team in innings pitched. He won Game 1 of the ALCS with six scoreless innings and then pitched six innings in each of his two World Series starts, both wins for the Royals.


Biggest contract: David Price, Red Sox (seven years, $217 million)

This was a landmark year in free agency, with a record $2.43 billion committed to free agents; the only other year to surpass $2 billion was 2020 ($2.13 billion). A record seven players signed deals of $100 million-plus and a record 14 of $50 million or more. If there was ever a more symbolic season of the risks involved in free agency, just consider those seven-year nine-figure deals:

• Price: He went 46-24 with a 3.84 ERA in four years in Boston and helped them win the World Series in 2018 (he arguably should have won MVP honors over Steve Pearce), so this was hardly a catastrophe. Still, Price didn’t pick up a single Cy Young vote with the Red Sox before they traded him to the Dodgers in the Mookie Betts deal.

• Zack Greinke (six years, $206.5 million): The best deal on the list, Greinke earned 21.2 WAR over the six seasons (although he received Cy Young votes in just one season).

Jason Heyward (eight years, $184 million): Flags fly forever.

• Chris Davis (seven years, $161 million): He would hit .196 in five seasons after re-signing with the Orioles.

Justin Upton (six years, $132.75 million): The Tigers traded him in 2017 to the Angels, who worked out a new extension (Upton had an opt-out clause), making it a seven-year, $150.25 million deal. He’s had two seasons above 2.0 WAR and will make $28 million in 2022.

• Johnny Cueto (six years, $130 million): He was good the first year and then battled injuries and went 21-22 with a 4.38 ERA over the final five seasons.

• Jordan Zimmermann (five years, $110 million). He went 25-41 with a 5.63 ERA for the Tigers.

Even most of the $50 million deals were questionable at best — Jeff Samardzija, Wei-Yin Chen, Mike Leake, Yoenis Cespedes (he opted out after one season and then signed a second deal with the Mets), Alex Gordon, Ian Kennedy and Ben Zobrist (flags fly forever!).

This might require a more detailed commentary in another column, but one reason we’re in this current labor impasse is what happened in 2016. Most of these big-money deals didn’t work out as anticipated; it’s understandable the front offices started spending less money — I mean, $80 million apiece for Chen and Leake. Front offices got smarter in their spending and the spigot dried up. The big stars still got paid, but the middle class wouldn’t see these wild deals.

Roll of the dice: Chris Davis, Orioles (seven years, $161 million)

What were the Orioles thinking? O’s fans have been asking this for six years. Davis was coming off a 47-homer season, but he was also one season removed from hitting .196, so there was a wide range of future outcomes. To make the contract even worse, the Orioles were basically bidding against themselves; no other team was going to come close to this offer, but owner Peter Angelos wanted Davis back in Baltimore.

Best bargain: Daniel Murphy, Nationals (3 years, $37.5 million)

Murphy was coming off that historic run in the postseason for the Mets, when he homered in six straight playoff games, but teams saw that power surge as a fluke and his lack of range at second base was viewed as a problem. The Nationals got him at a good price, his swing change did lead to more power, and Murphy finished second in the 2016 MVP voting after hitting .347 and leading the NL in slugging percentage and OPS (and he had another big season in 2017).


Biggest contract: Yoenis Cespedes, Mets (four years, $110 million)

Ahh, yes, those days of long ago when the Mets were a playoff team and Queens fell in love with Cespedes. He had signed a three-year, $75 million deal with the Mets the previous season, but it contained an opt-out that he exercised. The fans wanted him back and the Mets seemed to bow to public pressure and re-signed Cespedes as the top free agent in a weak class. He would play just 127 games over the four seasons.

Roll of the dice: Ian Desmond, Rockies (five years, $70 million)

This goes down as one of the strangest contracts over the past decade as the Rockies agreed to a $70 million deal — with the idea of making Desmond a super utility player. No, it never made any sense. Ben Zobrist, Desmond was not, as he played just three seasons with the Rockies, accumulating negative WAR.

Best bargain: Charlie Morton, Astros (two years, $14 million)

Morton had made just four starts with the Phillies in 2016 after tearing his hamstring in April, but the Astros’ front office — clearly ahead of the analytics curve at this time — noticed that Morton’s velocity had spiked during his abbreviated time in Philadelphia. Morton maintained that increased velocity (and started throwing his four-seamer more), stayed mostly healthy and went 29-10 over the two seasons and was a postseason hero in 2017, winning Game 7 of both the ALCS and World Series.


Biggest contract: Eric Hosmer, Padres (seven years, $144 million)

Ouch. Yu Darvish and J.D. Martinez were the other nine-figure players this offseason, but Hosmer got the largest total deal coming off a career-best .318/.385/.498 season with the Royals and entering his age-28 season. It’s easy to bash the deal now since Hosmer hasn’t come close to that triple slash line in his four seasons in San Diego (.264/.323/.415). The deal was widely criticized at the time, although to be fair Hosmer had been a good player in 2017 (4.3 WAR).

Roll of the dice: Jake Arrieta, Phillies (three years, $75 million)

Arrieta had an amazing two-year run from June 8, 2014 to June 22, 2016, going 42-12 with a 1.94 ERA, including a Cy Young Award in 2015. He was solid for the Cubs in 2017 (14-10, 3.53 ERA), but all his numbers were trending in the wrong direction. The Phillies bet on a turnaround — and bet wrong as he went 22-23 with a 4.36 ERA in three seasons.

Best bargain: Howie Kendrick, Nationals (two years, $7 million)

The Nationals had acquired Kendrick for the stretch run in 2017, liked what they saw, and re-signed him. While he was injured for much of 2018, he hit .344/.395/.572 in a part-time role in 2019 and then played World Series hero when he hit the go-ahead home run off Will Harris in Game 7.


Biggest contract: Bryce Harper, Phillies (13 years, $330 million)

Harper and Manny Machado were the two big tickets, both hitting free agency entering their age-26 seasons — the youngest free agents of this caliber since Alex Rodriguez in 2001. Machado got the higher AAV (10 years, $300 million) while Harper got the highest total value. So far, so good for Harper, including the 2021 NL MVP Award … although the Phillies have remained stuck in neutral.

Roll of the dice: Patrick Corbin, Nationals (six years, $140 million)

How do you judge a deal like this? Corbin was coming off a career-best season with the Diamondbacks and the Nationals added him to Scherzer and Stephen Strasburg to create a formidable trio. It paid off with a World Series title and Corbin pitched three scoreless innings in relief in the Game 7 victory. His next two seasons have not been good, however, and three years remain on the contract. Is one good season and a World Series worth it? Ask again at that 30-year reunion in 2049.

Best bargain: Charlie Morton, Rays (two years, $30 million)

Well, look who makes a repeat appearance. The Rays made a rare foray into free agency and signed Morton to a two-year contract. He pitched a career-high 194 innings in 2019 and finished third in the Cy Young voting and then helped the Rays to a second straight playoff trip in 2020 as they reached the World Series.


Biggest contract: Gerrit Cole, Yankees (nine years, $324 million)

The big prize in 2020, everyone expected Cole to sign with the Yankees — his favorite team as a kid — and he did. Who says baseball dreams don’t come true? The contract gives Cole an opt-out after 2024, although the Yankees can void that opt-out with a $36 million option for a 10th season in 2029. Cole hasn’t quite matched the spectacular season he had with Houston in 2019, but he has finished fourth and second in the Cy Young voting, although bitter Yankees fans expecting Cole to lead them back a long-awaited World Series will focus on his two-inning outing against the Red Sox in the wild-card defeat.

Roll of the dice: Stephen Strasburg, Nationals (seven years, $245 million)

No executive swings as big as Mike Rizzo — with some home runs along the way … and then this contract. After his dominant playoff run in 2019, Strasburg opted out of his existing deal. Strasburg’s injury history was certainly a concern, although perhaps a bit overstated: He had averaged 28 starts and 168 innings since his return from Tommy John surgery in 2012. Still, this felt like an emotional buy at the time for a pitcher, especially knowing they might lose Anthony Rendon (they did). There is time for Strasburg to get back on track, but he has made just seven starts in two injury-riddled seasons.

Best bargain: Wilmer Flores, Giants (two years, $6.25 million)

One thing the Giants have done so well the past couple of seasons under the front office regime of Farhan Zaidi is focus on a player’s strengths and figure out how that can help the team. Most teams saw Flores as a middle infielder with limited range and a mediocre OBP; the Giants saw a player who can hit lefties and serve as an effective, part-time player at three positions. In two seasons (and 649 plate appearances, about a full season’s worth), Flores hit .264/.328/.470 with 30 home runs.


Biggest contract: George Springer, Blue Jays (six years, $125 million)

The combination of a weak free-agent class and tight wallets after the COVID-shortened 2020 season led to the fewest total dollars ($1.32 billion) spent in free agency since 2012 ($1.30 billion). Springer signed the largest free-agent contract in Blue Jays history, edging out J.T. Realmuto for largest total value of the class while Trevor Bauer set an AAV record with his three-year, $102 million deal with the Dodgers. Springer’s first year came with mixed reviews as he hit well (.907 OPS), but played just 78 games.

Roll of the dice: Trevor Bauer, Dodgers (three years, $102 million)

The Dodgers already had the best projected rotation in the majors when they signed Bauer to a record-breaking contract, an excess of riches, because why not? Bauer was coming off a Cy Young Award in 2020 (short season caveat), but it came in a division where nobody hit and he had posted a 4.48 ERA in 2019. Anyway, Bauer made 19 starts before landing on the restricted list while his sexual assault investigation played out, forcing the Dodgers to trade for Max Scherzer, and Bauer’s future with the Dodgers remains in doubt. Maybe the site summed it up best: “The exiled pitcher made his return to social media just in time for the MLB playoffs and likely provided the Dodgers with bad juju.”

Best bargain: Charlie Morton, Braves (one year, $15 million)

It’s ol’ Charlie Morton for the third time. This is what teams hope for when they sign those 30-something veteran pitchers … but few keep producing like Morton has into his late 30s. Since turning 33 and playing for the Astros, Rays and Braves, he has gone 61-24 with a 3.34 ERA, won two World Series and pitched in a third. Total salary over those five seasons: $59 million. No wonder the Braves gave him a $20 million deal for 2022.

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