The best and worst MLB signings of the last decade

To bring a jolt of life to a lagging offense and add some pop to go along with Albert Pujols, the Cardinals struck a big deal with the Oakland Athletics to bring Holliday — and his expiring contract — aboard in August 2009. Holliday still spent the winter on the open market before deciding to re-up in St. Louis for the next seven years. Over his career as a Cardinal, he would hit .293 with 156 home runs, 616 RBIs, reach four All-Star Games and help lead the team a World Series victory in 2011. He also helped bridge the gap in the days after Pujols departed for Anaheim.

After years of coming up short, the Mets were hungry to get over the hump as the 2009 season came to close. In their quest to awaken their lineup, they made what looked to be a solid signing in Bay, who had been an All-Star for the Red Sox the year before with career highs in home runs (36) and RBIs (119). Yet, over three injury-riddled years with the Mets, Bay would not hit as many home runs in total as he did in his final season in Boston, finishing his time in New York with a .234 average and 26 homers.

V-Mart was the ultimate low-floor, high-ceiling, multi-year DH signing of the last decade. Although he missed 2012 with a torn ACL, in his three full seasons within the deal, Martinez produced a .321/.381/.487 split line and finished second in the 2014 MVP voting. On the second-place MVP year, he led the AL with a .974 OPS and became the first player since 1992 to hit 30 home runs while having 42 or less strikeouts.

One of the more puzzlingly bad contracts of all time was the one that went bad on the Red Sox (and later the Dodgers) for Crawford. He was an athlete on a level all his own and had the upside and track record to indicate it was a great investment for the club at the time. Perhaps he got paid and got satisfied or maybe he simply just lost his mojo, but after being a .296 career hitter and averaging 45 stolen bases a year before reaching Boston, Crawford hit only .260 with the Red Sox before being shipped to the Dodgers along with Adrian Gonzalez and Josh Beckett in 2012.

After defecting from the Cuban National Team, the Cuban Missile instantly became one of the most sought-after international free agents of all time. The stories of his otherworldly fastball proved true, as he quickly became one of the most dominant relievers in recent memory. Chapman has gone on to regularly rewrite the history books on fastest pitch ever and was a four-time All-Star in six years in Cincinnati.

Albert Pujols joining the Angels is a perfect case of either: a) a club bidding against itself, or b) purely ignoring what was to come. Granted, at the time of his signing, there had been no bigger of a guarantee in the game than Pujols, who had been the most consistently excellent player in baseball history over the first 11 years of his career. But when it came to his decline, it didn’t even bother to just rain — it poured immediately. Foot and elbow issues sped up his decline, and Pujols’s deal rapidly eroded into the biggest compensation albatross in the game before it was even a year old.

With a strong reputation built on his professional exploits in Cuba amplified by an eye-popping skills display on a subsequent workout tape following his defection, Cespedes was a late entry into the 2012 free agent pool. Surprisingly, his presence was capitalized on by the often-frugal Athletics, who along with the Red Sox, Tigers and Mets got premium value for a contract that paid out $10.5 million in its most expensive year. Cespedes averaged 26 home runs, 31 doubles and an .805 OPS over the life of the deal.

For as much of a value that Cespedes was upon arrival, he has become the opposite of such on the second half of his career. Since re-signing with the Mets, a string of injuries has rendered Cespedes into more of a burden than the franchise cornerstone he was intended to be. He has made $58 million over the past two years, despite playing just 119 games. Calf, hamstring and heel injuries cost him the 2019 season in full.

Although he experienced success with the Dodgers, Mariners and Red Sox before heading to Arlington in the winter of 2011, the future Hall of Famer Beltre’s signature portion of his career has come as a Ranger. The lively third baseman has finished in the top 10 of MVP voting four times, been a three-time Gold Glove and Silver Slugger recipient, and hit .308 over six years, including reaching the 3,000-hit mark this past summer.

Nostalgia played a big part in the Gordon contract, as the team opted to award its long-tenured outfielder the biggest contract in team history. At the time, Gordon had made three consecutive All-Star teams and had just helped Kansas City capture a World Series title. However, he was also coming off the worst offensive season of his career, a trend that continued over the life of his new contract. In the past four years, Gordon hit above .250 only once.

The Cardinals were forced to change directions quickly after winning the World Series in 2011, as both Albert Pujols and Tony La Russa left the organization shortly afterward. In response to losing Pujols, the club added Beltran, who replied with two superb seasons in St. Louis. Beltran turned in an All-Star appearance in each season with the club, which included 56 home runs, and played a huge part in the Cards returning to the World Series in 2013.

While no one can be sure if B.J. Upton changed back to his birth name of Melvin due to hiding from angry Braves fans, it would be hard to blame him if so. The Braves jumped at the opportunity to add the athletic center fielder to the spacious confines of Turner Field when he reached free agency as a 28-year-old. However, just two years into the deal, they could not get rid of him fast enough, as Upton produced a horrid .198/.279/.314 split line. Atlanta had to force him in as a third wheel into a package that also sent All-Star closer Craig Kimbrel to the Padres.

Although he was far from the first Japanese ace to cross the Pacific and make his way to the MLB, Darvish did represent a departure from the norm when he arrived. He was a younger, more power-oriented hurler than the likes of Daisuke Matsuzaka, Hideki Irabu or Kazuhiro Sasaki, who had preceded him. The Rangers signed him to a six-year deal that paid him $10 million annually. Darvish responded by affirming himself as one of the better pitchers in the American League, running up 200 strikeouts three times, including leading the circuit with 277 in his second season.

The club kept Davis in town via a seven-year, $161 million contract before the 2016 season. But since signing the deal, he has set some of the most infamous low-bar performances in MLB history. Davis has not hit above .200 since 2017, a span of 874 plate appearances. Even his once prodigious power has disappeared, as Davis has hit 28 home runs combined over the past two seasons. Despite receiving $69 million over the first three years of the deal, Davis has contributed a -3.8 WAR, by far the lowest in the MLB.

It is hard to say which coupon-rate deal Cruz’s services have been acquired for is better: the one-year, $8 million the Orioles paid him for an AL-best 40 home runs in 2014, as he repaired his stock from a PED suspension the year before, or his current deal. When taken at whole, the better value comes in the form of his current $57 million deal, in which he averaged 42 long balls over the first three years of the deal, which makes him the most frequent producer of homers in the game over the time span.

Detroit spent big to bring over Zimmerman, who was one of the fastest rising young starters in the game when he reached the open market. But the switch to the American League has not been a kind one, as Zimmermann has failed to reach double-digits in wins in any of his four seasons and his .379 winning percentage is the second-lowest in baseball since 2016 for pitchers with at least 90 starts.

On the heels of red-hot postseason performance where he hit .529 in route to winning NLCS MVP, Murphy left the Mets for their divisional foes in D.C. Subsequently, he became one of the most productive short-term signings of the decade. Murphy led the NL in doubles in each of his first two seasons with the Nationals and was NL MVP runner-up in 2016. Overall, he hit .329 in 342 games with the club.

It is not so much that Ellsbury has been horrible as Yankee; it's just that he was never worth the price New York paid for him in the first place. The talent was there, but the red flags were easy to see and avoid. At his peak, Ellsbury was one of the biggest speed/power dual threats in the game; however it was often offset by an unshakable string of injuries as well. Ellsbury missed the 2018 and 2019 seasons in full, before being released with two years and $26 million remaining on the deal.

Lester’s arrival in Chicago signaled a definitive change in direction for the Cubs, who at the time were moving past a last-place finish in the NL Central. However, Theo Epstein’s vision for rebuilding the organization was just taking shape, and the proven track record of Lester played a vital part in rapid turnaround the team would experience in subsequent years. In the Cubs' long-awaiting championship year of 2016, Lester finished second in the NL Cy Young Award vote, going 19-5 with a 2.44 ERA, before winning six postseason games, including three in the World Series.

The risks that came associated with Hamilton were clear when the Angels jumped at the opportunity to lure away a major impact-maker from their chief in-division foes in Arlington. Hamilton had both a sketchy personal and health history, and many of the worst-case scenarios that could come true did. He made it to the field for only two of the five years he was signed for, contributing just 31 home runs in just over 1,000 plate appearances. Ultimately, he was shipped back to Texas with the Angels still on the hook for much of the tab — a bill they finally got out from under this season despite him last suiting up for the club in 2014.

The anticipation of decline or injury is always the downside of agreeing to a massive, long-term deal, especially with a pitcher. But so far, so good for the Nationals in their pact with Scherzer, as they have increasingly gotten the best of the now three-time Cy Young Award winner. Since joining the club, Mad Max has led the NL in strikeouts three times, notched a 20-strikeout game, tossed a pair of no-hitters and helped pitch the club to World Series. He has become a Hall of Famer as National and has been the most valuable open market pitching addition in history.

The Marlins went in big to land Chen to lead their rotation in 2016, and he never came close to returning the value. The lefty won 13 games over four seasons before being bad enough that even amid a massively intentional rebuilding effort, the club couldn’t justify starting him anymore. Chen was moved to the bullpen in 2019, where he pitched to a 6.59 ERA over 45 games before the Marlins cut their losses and released him with $8 million left on the final year of his deal.

Not once, but twice did Greinke master the art of navigating the waters of free agent. In his first foray headed into the 2013 season, he inked a lucrative six-year deal with the Dodgers, which included an opt-out clause after three years. Well, after three seasons in Dodger blue that saw him go 51-15 and post a 1.66 ERA in 2015, Greinke bet on himself and headed back into free agency, where the Diamondbacks rewarded him even more handsomely to lead their staff. Greinke, now with Houston, won 67 percent of his starts during that deal, was an All-Star in three of the four seasons and extended his Gold Glove streak to six years.

After making a strong second-half rebound from a disastrous start the year before, the Orioles felt confident enough in the upside of Jimenez to sign him to a lucrative, multi-year pact. It was a decision that continues to haunt the O’s, who suffered through Jimenez’s continued bouts with inefficiency and inconsistency. Over the lifetime of the deal, Jimenez never finished a season with an ERA south of 4.00 or a WHIP of 1.30. Over 2016-17, he produced a 14-23 record with a 6.13 ERA. 

Turner has been the glue that has driven the Dodgers’ lineup since arriving in 2014, hitting .302 over six full seasons with the club. So it was no mystery that L.A. wasted no time in re-upping with the third baseman when he hit the open market in the winter of 2016. The Dodgers signed the versatile third baseman to an initially team-friendly deal that totaled $25 million over the first two years, before capping at $20 million in 2020. The decision has aged well, as has Turner, who’s 14.0 WAR since 2017 is among the best for all players age 30 or older.

When the Red Sox finally cut the cord on their pact with Sandoval midway through the 2017 season, it could be argued that it was already well overdue. All of the conditioning concerns that scared teams off from offering him even a moderately long-term deal when he hit the open market after the 2014 season came true, as Sandoval managed only 161 games over parts of three years, hitting .237 in the process, before being outright released with two-and -a-half years left on his deal.

Cain reached Milwaukee as a part of the deconstruction of the championship Kansas City Royals teams and instantly had a bar-raising effect in his new home. The Brewers have twice reached the postseason during Cain’s tenure, with him being selected an All-Star in 2018, then winning the NL Gold Glove in center field the following season. Since moving to the National League, only Mike Trout has contributed a higher overall WAR among center fielders, while Cain’s 4.6 defensive WAR is the best at the position.

This massive contract ever awarded to a free agent outfielder at the time. Although he has remained an elite performer with the glove, capturing his fifth and sixth career Gold Glove Awards as a Cub, his offensive returns have left much to be desired. Of all players who have spent at least 90 percent of their time as an outfielder since 2016, Heyward's .755 OPS is among the lowest. In 2019, he exercised his player option that will guarantee him another $86 million through 2022.

Morton has become baseball’s greatest value over the past three seasons. Over the course of his last two contracts, Morton has made $29 million while accounting for a 10.7 WAR. His $30 million contract was the largest spend in franchise history for the Rays, and Morton held up his end of the bargain. Morton turned in career-highs in wins, innings pitched and strikeouts all while allowing the fewest home runs per nine innings in the majors. The 36-year-old finished third in AL Cy Young Award voting and was the 24^th highest-paid starting pitcher in the game.

Melancon’s pact with the Giants was, at the time, the richest ever given to a relief pitcher, earning him an average of $19 million per season. However, Melancon never converted more than 11 saves during his 2.5 years with the club, converting on only 55.8 percent of opportunities. Eventually, he was moved out of the ninth inning, before being traded to the Atlanta Braves in 2019. After going 11-for-11 in save opportunities as a Brave, he posted a 12.00 ERA in the postseason.

Instead of spending big to keep Bryce Harper in town, the Nationals spent big on Corbin ahead of the 2019 season, making him the 10^th highest-paid pitcher in the game. In year one, Corbin did not disappointment, going 14-7 with 3.25 ERA and notching 238 strikeouts. Most importantly though, he became a versatile weapon in the postseason, making three starts and working another six appearances out the bullpen, helping the Nationals to their first World Series title.

Davis had been one of the most dominant relievers of the past decade, being named to three-consecutive All-Star Games and helping the Royals to the 2015 World Series title. Although Davis led the NL in saves in 2018, two years into the deal, things are looking great. Davis was tagged to the tune of an .872 OPS and allowed an 8.65 ERA in 2019 – a year where he was fourth-highest paid relief pitcher in the game. His 2019 -1.3 WAR was the lowest of a pitcher with at least 15 saves in the last decade.