Worst MLB Free-Agent Contracts Since 2000

Free agency is one of the most captivating parts of the MLB offseason. Star players don't often hit the open market, so landing a marquee free agent is always exciting.

Sometimes, though, the best moment of the signing is when the deal is struck or the press conference ends. Unfortunately for teams, optimism can vanish within a year or two—yet they remain on the hook for many millions of dollars.

And the past two decades of free agency have brought a large group of disastrous agreements.

Key considerations are monetary value and player performance in the contract's duration. Someone like Albert Pujols (10 years, $240 million), for example, has a glaringly bad salary at the end of his pact, but he produced for about half the deal. The focus is on high-dollar signings who never lived up to the financial numbers.

Contract: Eight years, $121 million

In 1999 and 2000 combined, Mike Hampton went 37-14 with a 3.02 ERA for the Houston Astros and New York Mets. He parlayed that success into a massive deal with the Colorado Rockies, who signed Hampton and Denny Neagle before the 2001 season to bolster the rotation.

But as Hampton's impressive bat thrived in the Denver air, his primary responsibility—pitching—didn't follow suit.

The left-hander enjoyed a 9-2 start in 2001, but Hampton gave up 92 earned runs in the next 112.1 innings. His ERA ballooned to 5.41 by the end of the regular season. And in 2002, he posted a 6.15 ERA. Hampton's two-year stint concluded with a 21-28 record, 5.75 ERA, 88 ERA+ and an unsightly 1.68 WHIP.

Colorado shipped him and Juan Pierre to the Florida Marlins, who then flipped Hampton to the Atlanta Braves.

Contract: Seven years, $126 million

Barry Zito really tested the "best ability is availability" trope.

After a seven-plus-year stretch on the Oakland A's that included a Cy Young and three All-Star teams, Zito crossed the bay and joined the San Francisco Giants. The left-hander signed the largest contract for a pitcher in MLB history in December 2006.

Though he started 32-plus games in five seasons and 25 in another, Zito rarely pitched at a high level. His best years (4.03 ERA, 105 ERA+ in 2009 or 4.15 ERA, 85 ERA+ in 2012) with the Giants barely edged his worst season (4.48 ERA, 102 ERA+) in Oakland.

If you're looking for a bright side, Zito won two rings. However, he didn't pitch in the 2010 postseason before making three appearances—including one World Series win—in 2012.

San Francisco had much higher expectations than a 63-80 record, 4.62 ERA and 87 ERA+ for $126 million.

Contract: Seven years, $142 million

Carl Crawford debuted in 2002 and assembled a strong nine-year stretch with the Tampa Bay Rays. He smacked 215 doubles, 105 triples and 104 homers during his time in Tampa, making four All-Star teams and winning a Gold Glove.

His career only went downhill after he joined the Boston Red Sox in December 2010.

Crawford hit just .255 in 2011, and then wrist and elbow injuries limited him to 31 games the next season. He mustered 0.9 WAR in 161 appearances, ending his brief tenure with a .292 on-base percentage and bad memories of a "toxic" environment.

Shortly before the 2012 trade deadline, Boston dealt him to the Los Angeles Dodgers in a massive trade that included Adrian Gonzalez and Josh Beckett. Injuries continued to plague Crawford until the Dodgers released him in June 2016.

Contract: Five years, $125 million

Josh Hamilton overcame injuries and substance abuse to fulfill his promise from his days as an elite Tampa Bay Rays prospect. From 2008 to 2012 on the Texas Rangers, he won an MVP, made five All-Star teams and brought home three Silver Slugger awards.

Following the 2012 season, he left Texas for an AL West rival in the Los Angeles Angels.

That, unfortunately, is where the comeback story hit a rougher on-field chapter. He managed only 2.7 WAR in two seasons, striking out 266 times in 1,017 plate appearances and even going hitless in the 2014 playoffs.

Los Angeles paid $68.4 million of Hamilton's remaining $74.4 million in a salary-dump trade that returned him to Texas.

Shoulder and knee injuries limited the outfielder to 50 appearances in 2015 before he retired.

Contract: Five years, $75.25 million

After the 2012 season, the Braves signed B.J. Upton to the largest free-agent contract in franchise history. Months later, they traded for his brother Justin. They would join rising star Jason Heyward to give Atlanta an incredible outfield.

That was the hope, at least. The problem was, suddenly, B.J. stopped positively impacting the game.

In two seasons with the Braves, Upton hit a ghastly .198 with a 31.5 percent strikeout rate. Atlanta benched him in the 2013 playoffs—where he struck out in all three pinch-hit chances. Heyward never improved as a hitter, but he at least provided superb value defensively; B.J. was never better than average in center field.

The Braves attached his contract to a trade, sending All-Star closer Craig Kimbrel to the San Diego Padres in April 2015.

Contract: Seven years, $153 million

As a member of the Red Sox in 2011, Jacoby Ellsbury belted 32 homers and drove in 105 runs. Ellsbury won a Gold Glove and Silver Slugger, made his first All-Star team and finished second in MVP voting. And in 2013, he stole an MLB-best 52 bases.

Those two seasons led the New York Yankees to swipe Ellsbury from the rival Sox in December 2013, but the decision failed badly.

Ellsbury had a reasonably successful 2014 before a string of injuries derailed his career. He missed at least 50 games in 2015 and 2017 and the entire 2018 and 2019 seasons. Ellsbury slugged just .386 in 520 games with the Yankees.

New York whiffed on Kei Igawa and Carl Pavano in the 2000s, but the total value of Ellsbury's contract puts him on this list.

Contract: Seven years, $72.5 million

After defecting from Cuba, Rusney Castillo landed an enormous deal with Boston in August 2014. Ironically, that is also the exact reason he didn't appear in the majors in the last four seasons.

Castillo made his MLB debut in 2014 and played 80 games in 2015, but a .679 OPS in 337 plate appearances didn't impress. After the Sox demoted him in 2016, luxury-tax implications deterred the organization from bringing Castillo back to the majors and allowing him a chance to earn, at worst, a backup role.

He made $11-plus million per season in Triple-A, but that salary trapped him in the minors. From 2016 to 2019 with Pawtucket, Castillo posted a .294 average and .764 OPS.

Castillo became a free agent following the 2020 season.

Contract: Five years, $95 million

Pablo Sandoval won three championships with the San Francisco Giants in the early 2010s, playing a key role in a pair of the title runs.

The two-time All-Star and 2012 World Series MVP consistently hit for a decent average with 25-plus doubles and double-digit homers on the Giants.

But within two seasons and a few months, the $95 million deal Sandoval signed in November 2014 turned into a nightmare for Boston.

Sandoval appeared in just 161 games with the team from 2015 to 2017, posting a .237 average with a .286 on-base percentage while striking out more frequently than ever. That lack of production compounded his woes at third base, where he posted minus-15 defensive runs saved.

Releasing him in July 2017 cost the Red Sox roughly $50 million.

Contract: Five years, $110 million

Before the 2015 campaign, the Detroit Tigers lost Max Scherzer to the Washington Nationals. The following offseason, Detroit swiped Jordan Zimmermann—a two-time All-Star—from the Nats. He'd posted a 3.32 ERA in seven years and 1,094 innings.

Zimmermann had a brilliant first month in Detroit, allowing only two earned runs in 33 frames to win five straight starts.

That wasn't sustainable, of course. But his tenure became a disaster.

While dealing with a minor injury in most seasons, Zimmermann never finished with an ERA better than 4.52 for the Tigers. He tossed 514.1 innings, mustering a 25-41 record, 5.63 ERA and 80 ERA+ throughout a contract that ended in 2020.

Contract: Seven years, $161 million

Articles of this nature tend to dehumanize an athlete. Player X signed a contract worth Value Y, and let me explain why it was A Bad Thing That Happened. Chris Davis is a reminder of how Player X hates the underperformance more than anyone watching from the sidelines.

"I have no clue what I'm doing at the plate," Davis said in late 2018, per Stephanie Apstein of Sports Illustrated.

Davis certainly used to know.

In 2013, he paced the American League with 53 homers and 138 RBI. Davis had a rough 2014 yet recovered to smack an AL-best 47 homers the next season. Sure, he struck out a league-worst 208 times, but Davis' power atoned for his whiffs.

Until it didn't. Following a 38-homer year in 2016, Davis' production declined sharply. He's hit .185 with a 37.4 strikeout rate since the beginning of the 2017 campaign. In the pandemic-shortened 2020 season, Davis went 6-for-52.

His contract runs through 2022.

Stats courtesy of FanGraphs and Baseball Reference unless otherwise noted.