Ranking the 12 worst contracts in MLB ahead of 2021 season

The Deal: Five Years, $82.5 Million
Total Remaining: One Year, $14.5 Million
2021 Salary: $14.5 Million

After Fowler helped the Chicago Cubs snap a 108-year World Series drought in 2016, the division-rival Cardinals rewarded him with a lucrative five-year pact. Unfortunately for the Cardinals, Fowler's offensive production has plummeted since his second season in St. Louis, as he slashed .233/.317/.389 during the pandemic-shortened season. Fowler, who will turn 35 before the start of the 2021 season, is entering the final season of his contract.

The Deal: Seven Years, $217 Million
Total Remaining: Two Years, $64 Million
2021 Salary: $32 Million

One of Dave Dombrowski's first moves when he took over the front office for the Boston Red Sox was to sign Price to a seven-year/$217 million deal. On one hand, the deal did ultimately help the team to win a World Series in 2018. Still, it's hard to say it's aged well. Through the first four seasons of the contract, Price posted a 3.84 ERA, which means he was very serviceable, just not to the point that it justified his contract. Price was traded to the Dodgers as part of the Mookie Betts deal before the 2020 season, but ultimately opted out of the year because of COVID-19. He'll return to the defending World Series Champions in 2021 with $64 million still remaining on his contract. RADIO.COM MLB Insider Jon Heyman estimates that the Red Sox will be responsible for half of the money still owed to Price on his contract.

The Deal: Three Years, $50 Million With $15 Million Club Option For Fourth Season
Total Remaining: One Year, $20 Million, Plus $15 Million Club Option
2021 Salary: $20 Million

McCutchen was having a tremendous first season in Philadelphia, before suffering a season-ending torn ACL in June of 2019. McCutchen did still homer 10 times and drive in 34 runs in the pandemic-shortened 2020 season, though his defense fell off of a cliff. He's past the point of his career where he can play center field, and may be reaching a similar point in terms of being able to proficiently play left field. In 402 1/3 innings in left field for the Phillies in 2019, McCutchen posted four defensive runs saved. Post knee surgery, though, McCutchen struggled in left field, posting -8 defensive runs saved in 302 innings in 2020. At this stage of his career, McCutchen is probably best suited to be a DH, though at the time of publication, we aren't sure if the universal DH will return in 2021. Even if it does, it's unlikely McCutchen is so productive offensively in 2021 that it justifies the $20 million salary he'll collect.

The Deal: Seven Years, $245 Million
Total Remaining: Six Years, $210 Million
2021 Salary: $35 Million

The Nationals had two franchise icons - Strasburg and Anthony Rendon - become free agents after they won the 2019 World Series. While Strasburg was the reigning World Series MVP, early returns suggest that they picked the wrong one to re-sign. Rendon, who signed an identical seven-year/$245 million deal with the Los Angeles, graded out as the fifth-most valuable offensive player in baseball in 2020. Strasburg was limited to just five innings during the 2020 season, with August carpal tunnel surgery ending his season before it ever really got started. Strasburg's history suggests that he'll pitch at an elite level, at least early on in the contract, when he's healthy. The problem is that injuries have been a recurring theme during the former No. 1 overall pick's career, and as he approaches his mid-30s, that's unlikely to change.

The Deal: Eight Years, $159 Million With $22 Million Club Option For Ninth Season
Total Remaining: One Year, $21.4 Million, Plus $22 Million Club Option
2021 Salary: $21.4 Million

At his peak, Posey was a Hall of Fame-caliber player, which is what earned him one of the largest deals in the history of the position. However, Posey opted out of the 2020 season because of COVID-19, and it's been since 2017 that he's played 115 or more games in a season. The former MVP will be the team's starting catcher in 2021, per manager Gabe Kapler. That said, if No. 1 overall prospect Joey Bart impresses this upcoming season, it will likely be his job to lose in 2022. Posey has spent his entire career with the Giants, and has suggested he wouldn't want to play for another organization. Still, if the 33-year-old hopes to continue his career beyond the 2021 season, it may have to be for another team.

The Deal: Eight Years, $184 Million
Total Remaining: Three Years, $65 Million
2021 Salary: $21 Million

In his lone season with the Cardinals in 2015, Heyward had a career year, slashing .293/.359/.439 with 13 home runs, 79 RBIs, 23 stolen bases, a staggering 26 defensive runs saved and a 5.6 fWAR. Considering he was only entering his age-26 season when he became a free agent, you can see the logic in signing Heyward to a megadeal before the 2016 season. Unfortunately for the Cubs, while Heyward has won two Gold Glove Awards as a member of the team, his bat hasn't consistently performed at the star level Chicago hoped for when they signed him to such a massive contract. Heyward actually posted a negative offensive WAR in his first season with the team, and while he's coming off of a pretty productive season in terms of getting on base, you can bet the Cubs would like a mulligan on Heyward's deal.

The Deal: 13 Years, $325 Million With $25 Million Club Option For 14th Season
Total Remaining: Seven Years, $208 Million, Plus $25 Million Club Option
2021 Salary: $29 Million

Brian Cashman is a Hall of Fame-caliber executive, but his decision to trade for reigning National League MVP Giancarlo Stanton after the 2017 season stands out as one of the worst transactions in recent memory. Though there were some extenuating circumstances, Stanton often dealt with injuries during his eight seasons with the Miami Marlins. And after a good, not great, first season in the Bronx, that's reared it's ugly head in New York. Over the past two seasons, Stanton has played in just 41 of a possible 222 games. His absence has been made worse by the fact that Aaron Judge has struggled to stay healthy over the same timespan. There's a very real chance Stanton will hit 500 home runs during his career, but if the Yankees had waited just one more offseason, they could have spent similar money on Bryce Harper to play the outfield, rather than Stanton, who has become an injury-prone DH.

The Deal: 10 Years, $225 Million With $20 Million Club Option For 11th Season
Total Remaining: Three Years, $75 Million, Plus $20 Million Club Option
2021 Salary: $25 Million

A six-time All-Star, Votto will have a compelling Hall of Fame case when his career concludes. Unfortunately for the Reds, who are cutting costs like crazy this offseason, they're likely stuck with Votto's contract, which has become pretty ugly. Granted, Votto homered 11 times, drove in 22 runs and walked 37 times in 2020, so he's not at the stage of his career where he brings no value to a team anymore. But is the 37-year-old worth $75 million over the next three seasons? Not even close.

The Deal: Five Years, $145 Million With $20 Million Club Option For Sixth Season
Total Remaining: Four Years, $115 Million, Plus $20 Million Club Option
2021 Salary: $30 Million

Between 2012 and 2018, Sale had one of the most dominant seven-year stretches that a left-handed pitcher has ever had, culminating in him helping lead the Red Sox to a World Series title in 2018. Since signing a five-year/$145 million extension with the team in March of 2019, though, Sale simply hasn't been able to stay healthy. The lanky southpaw was limited to 25 starts in 2019, with left elbow inflammation ending his season. Sale would ultimately undergo Tommy John surgery on March 30, 2020, which kept him from pitching at all this past season, and will cut into some - if not all - of 2021. Now 31, Sale may still be an excellent pitcher, but injuries have kept the seven-time All-Star from being able to earn his contract.

The Deal: 10 Years, $240 Million
Total Remaining: One Year, $30 Million
2021 Salary: $30 Million

Between 2003 and 2011, Pujols' last nine seasons with the Cardinals, he slashed .330/.425/.624 with 374 home runs, 1,072 RBIs and a 68.6 fWAR. In his first nine years with the Angels, Pujols has slashed .257/.312/.448 with 217 home runs, 771 RBIs and a 6.2 fWAR. The Angels never got a single season of Pujols' peak, and have had to deal with a lot of seasons where he's been an objectively below-average player. Given that his deal has helped contribute to wasting the peak of Mike Trout to this point, it's very possible that Pujols' contract will go down as the worst in baseball history.

The Deal: Eight Years, $248 Million With $30 Million Mutual Options For Ninth And 10th Seasons
Total Remaining: Three Years, $94 Million, Plus $30 Million Mutual Options
2021 Salary: $30 Million

At the height of his powers, Cabrera was one of the greatest right-handed hitters in MLB history. Unfortunately for the Tigers, that point has long since passed, which leaves the Tigers to ride out the remaining years for a player that's been worth just 0.5 fWAR over the last four seasons. The part that really burns about Cabrera's extension is that then-general manager Dave Dombrowski re-upped Cabrera for eight more seasons in March of 2014, despite the fact he couldn't become a free agent until after the 2015 season. Regardless of what had been done in the past, it wasn't difficult to figure that an eight-year extension beginning in a slugger's age-33 season probably wouldn't age well. Now, the Tigers find themselves on the hook for three more guaranteed seasons with Cabrera, and assuming they decline their half of $30 million mutual options in 2024 and 2025, they'll have to pay him $8 million in each season not to play for the team.

The Deal: Seven Years, $161 Million
Total Remaining: Two Years, $34 Million
2021 Salary: $17 Million

Despite hitting just .196 in 2014, the Orioles were fooled by the massive power numbers that Davis put up in 2013 and 2015, which led them to rewarding Davis with a seven-year/$161 million deal in January of 2016. Ironically, since signing that extension, Davis has hit just .196 in parts of five seasons. Between 2012 and 2015, Davis hit 159 home runs. Over the past five years, Davis has 92 home runs, 38 of which came in the 2016 season. While some sluggers like Ryan Howard had major injuries that affected their ability to live up to their massive extensions, Davis simply has fallen off, without an exact explanation for why his production has plummeted.