Re-Grading the Biggest MLB Free-Agent Signings of the Last 2 Decades

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Players and owners are squabbling over money with the truncated 2020 Major League Baseball season hanging in the balance. 

While we wait, hoping for a resolution that leads to actual MLB baseball, let's talk money. Specifically, let's examine the 10 biggest MLB free-agent contracts from the past two decades by total dollar value (which makes them, by definition, the biggest MLB free-agent contracts of all time) and assign grades with the benefit of hindsight.

We'll eliminate some of the megadeals inked this winter and in the winter of 2018-19 since we don't have a large enough sample size. We're also looking only at guys who signed as free agents, so lucrative extensions don't count.

Some of the deals that made the list are completed; others have played out far enough to merit a report-card mark.

Grades are based on players' performances relative to their paychecks and whether they've helped or hindered their respective clubs' contention hopes.

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Gerrit Cole, New York Yankees: 9 years, $324M (2019-20 Offseason)

When play resumes, the Yankees are hoping Cole, who they signed away from the American League champion Houston Astros, will be the ace who pushes them over the hump and wins New York its first ring since 2009.

Anthony Rendon, Los Angeles Angels: 7 Years, $245M (2019-20 Offseason)

Fresh off a World Series win with the Washington Nationals, third baseman Anthony Rendon signed a massive pact with the Angels that will join him with reigning American League MVP Mike Trout in the middle of the Halos lineup. It should make Los Angeles a factor in the AL West.

Bryce Harper, Philadelphia Phillies: 13 Years, $330M (2018-19 Offseason)

Harper's first season in Philadelphia wasn't an unmitigated success. He struggled at times, and the Phils failed to make the postseason. But he finished with 35 home runs and 114 RBI. At age 27 and with 12 years left on his deal, he has plenty of time to make good in the City of Brotherly Love.

Manny Machado, San Diego Padres: 10 years, $300M (2018-19 Offseason)

Machado hit a career-worst .256 in his first season with the San Diego Padres, though he added 32 home runs. As with Harper, he's only 27 and has ample opportunity to help the Friars and their strong, emerging young core become a contender.

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The New York Yankees went on a spending spree prior to the 2009 season, and it worked in the short term as they won a title that year with an expensive, star-studded roster.

First baseman Mark Teixeira did more than his part, hitting 39 home runs with a .948 OPS, winning a Gold Glove and finishing second in AL MVP voting.

Teixeira would enjoy two more productive seasons with New York before injuries started to sap his stats and playing time. 

Ultimately, he won three Gold Gloves, made two All-Star appearances and posted an .822 OPS in pinstripes. The Yanks paid for an aging player on the back end, but considering they won a Commissioner's Trophy with Teixeira in the heart of the lineup, this one comes out on the above-average end of the spectrum.

Grade: B

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When the Chicago Cubs signed Jason Heyward prior to the 2016 season, they were hoping to add a key piece to their strong, largely homegrown lineup and win their first title since 1908.

They succeeded on the latter count.

Heyward was a contributor to that drought-busting club and won a Gold Glove for his play in right field. But he slashed just .230/.306/.325.

In four seasons with the Cubs, Heyward owns a .711 OPS. His defense remains exemplary, but he'll never be the middle-of-the-order bat many projected him to be early in his career with the Atlanta Braves.

Chicago got its long-overdue trophy. However, the $21 million it owes Heyward in 2020 and 2021 and the $22 million it'll pay him in 2022 and 2023 make this look like an overpay for a relatively weak-hitting corner outfielder.

Grade: C-

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After leading baseball with a 222 ERA+ and 0.844 WHIP for the Los Angeles Dodgers in 2015, Zack Greinke opted out of his contract and signed a bigger one with the Arizona Diamondbacks.

The right-hander's ERA ballooned to 4.37 in his first season with the Snakes, though he rebounded with a couple of solid, 200-plus-inning seasons in 2017 and 2018 that featured ERAs of 3.20 and 3.21, respectively.

Last year, the D-backs dealt him to the Houston Astros prior to the trade deadline. He helped the 'Stros win the AL pennant and pitched well in their seven-game World Series loss to the Washington Nationals.

Greinke will be a key piece for Houston going forward after it lost ace Gerrit Cole to free agency. The Diamondbacks will pay $24 million of the $77 million he's owed over the next two seasons, but they netted a nice package of prospects (first baseman Seth Beer, right-handers J.B. Bukauskas and Corbin Martin and utilityman Josh Rojas) that could set them up for the future.

Greinke is 36, so there's some risk of regression for Houston. The Diamondbacks also made the playoffs just once with their expensive ace on the roster. But this deal was far from a disaster.

Grade: B-

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Since signing his megadeal prior to the 2015 season, Max Scherzer has been nothing short of brilliant for the Washington Nationals.

Over five seasons in the nation's capital, Mad Max has made five All-Star teams, won two Cy Young awards, paced baseball in strikeouts twice and, in 2019, led the Nats to the first championship in franchise history.

Overall, he owns a 2.74 ERA with 11.7 strikeouts per nine innings for Washington.

The 35-year-old righty could never throw another inning for the Nationals, and this deal would still be great. But there's no reason to assume he won't keep being an ace through 2021.

Grade: A

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The Detroit Tigers opened their wallet wide to sign Prince Fielder before the 2012 season, bringing the slugger to the team with which his father, Cecil, enjoyed his best seasons.

It seemed like a match, and Fielder was excellent in his first year with the Tigers, clubbing 30 home runs with a .940 OPS.

His numbers dipped in 2013 (25 home runs, .819 OPS), and Detroit traded him and $30 million to the Texas Rangers for second baseman Ian Kinsler that offseason. It was a change-of-scenery swap for both players.

Kinsler was a productive player in four seasons with Detroit, hitting .275 overall and winning a Gold Glove in 2016.

Fielder, meanwhile, battled injuries during his tenure with Texas. He hit .305 over 158 games in 2015, his only full season. But overall, he posted a disappointing .760 OPS with the Rangers before a neck injury forced him to retire following the 2016 campaign.

In the end, Fielder's injury issues derailed this deal for Texas. While the Tigers got some value back from Kinsler, this was an overall disappointment for all sides.

Grade: D

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David Price had his moments after signing with the Boston Red Sox prior to the 2016 season.

He led MLB with 230 innings pitched in the first year of his deal, and he posted a 1.98 ERA in three appearances during the 2018 World Series, helping Boston win its fourth title since 2004.

Overall, though, Price was a mixed bag in four seasons with Boston. He battled injuries and inconsistency and rarely pitched like the unambiguous ace the Sox were paying him to be.

And so, this winter, Boston dealt the 34-year-old lefty, along with All-Star right fielder Mookie Betts, to the Los Angeles Dodgers for a package of prospects headlined by promising outfielder Alex Verdugo. 

The Red Sox will pay half of the $32 million Price is owed annually through 2022. It was a prudent move for a team that needs to retool, if not rebuild.

But as for Price's time in Beantown, it'll mostly be remembered with a "meh" despite the '18 championship and the occasional flashes of his old brilliance.

Grade: C-

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When the Seattle Mariners backed up the Brink's truck for Robinson Cano entering his age-31 season, they hoped they were signing a middle-of-the-order bat who would return them to the postseason for the first time since 2001.

Cano wasn't terrible during his tenure in the Pacific Northwest. Overall, he hit .296 with an .826 OPS in five seasons. He made three All-Star teams and twice finished in the top eight in AL MVP voting. 

But the M's were never able to build a winner around him, and Cano became an aging payroll albatross who served an 80-game suspension for violating MLB's performance-enhancing drug policy in 2018. That offseason, the Mariners traded him and closer Edwin Diaz to the New York Mets.

Seattle netted outfielder Jay Bruce, reliever Anthony Swarzak, right-hander Gerson Bautista and former first-round picks Jarred Kelenic (2018) and Justin Dunn (2016) from New York. It also sent back $20 million.

While this wasn't a complete loss, most M's fans will rightly associate the Cano deal with a period of ongoing futility.

Grade: C-

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Albert Pujols should be a first-ballot Hall of Famer when the time comes. Unfortunately for the Los Angeles Angels, he built the bulk of that HOF resume while playing for the St. Louis Cardinals.

Pujols was a nine-time All-Star and three-time National League MVP when the Angels signed him prior to the 2012 season. Since then, he's been in a steady decline.

Pujols swatted 30 home runs with 105 RBI in his first season with the Halos. He hit 40 home runs with 95 RBI in 2015 and tallied 31 homers and 119 RBI in 2016. There have been stretches in which he's looked like his old self.

But there's no sugarcoating the .258/.314/.450 slash line he's amassed in eight seasons with Los Angeles, especially when you compare it to the .328/.420/.617 line he put up in his 11 years with St. Louis.

The Angels owe Pujols $29 million in 2020 and $30 million in 2021, when he'll be 41 years old. During his tenure, they've played exactly one postseason series despite employing Mike Trout, the best player on the planet.

This is the definition of a club paying a player for what he was rather than what he is or will be.

Grade: D-

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The story of Alex Rodriguez's big paydays comes in two parts.

The first began when he signed a then-record deal with the Texas Rangers prior to the 2001 season. In three years with Texas, Rodriguez hit 156 home runs, posted a 1.011 OPS, won two Gold Gloves for his play at shortstop and earned the 2003 AL MVP award.

Texas, however, squandered his talents and finished a distant fourth place in the AL West every year Rodriguez was on the roster.

And so, in February 2004, the Rangers traded their star to the New York Yankees for second baseman Alfonso Soriano and $67 million of the $179 million remaining on his contract.

Rodriguez kept raking for the Yanks and won two more MVPs (2005 and 2007). After the '07 campaign, he opted out of his existing contract and became a free agent.

This ended up being a strange deal for the Rangers. They got three brilliant years of A-Rod's prime and two All-Star seasons from Soriano, who they then traded to the Washington Nationals for an underwhelming package, all while never making the playoffs.

As for the Yankees, they got more excellence from Rodriguez and made the playoffs every year.

Despite the divergent results of both clubs, there's no question Rodriguez earned his hefty paycheck each season with Texas and New York prior to his opt-out decision.

Grade: A

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After he opted out, the Yankees re-upped Rodriguez to another massive pact. This one yielded far more tumultuous results.

Rodriguez made three more All-Star teams with New York and helped it win the World Series in 2009. But his numbers began to decline with age and injury.

Then the hammer dropped, and he was suspended for the entire 2014 season for performance-enhancing drug use. That wiped out $25 million of his contract and put a dark cloud over his impressive career.

He returned to hit 33 home runs in 2015, but he was met with boos and disdain by many fans. After hitting .200 over 65 games in 2016, he retired as one of the more accomplished yet controversial players in baseball history.

He did a lot for the Yankees on the field, but this second chapter of his 13-year run with the team featured more low moments than high ones.

Grade: D+

All statistics courtesy of Baseball Reference; contract information courtesy of SpotRac and Baseball Prospectus.