5 big money MLB moves that backfired on teams

MLB players are signing earth-shattering deals this offseason. Shohei Ohtani signed a 10-year, $700 million deal, making it the largest professional contract in sports. Yoshinobu Yamamoto signed a huge deal at $325 million, making it the richest pitcher contract in the sport's history.

Baseball players are some of the richest-paid professional athletes. But what happens when teams dish out big-time money for players who underperform? Let's take a look at some of the worst deals in league history.

Top 5 MLB deals that backfired on teams

#5. Bobby Bonilla

You cannot talk about questionable contracts without mentioning Bobby Bonilla. Bonilla is famous for his absurd contract with the Mets. From 2011 until 2035, Bonilla will receive at least one million dollars yearly.

The Mets cut the aging slugger during the 1999 season. However, he was still owed $5.9 million. Instead of paying out his contract upfront, Mets' owner Fred Wilpon struck a deal with the player's camp. The team agreed to pay Bonilla in installments with annual interest.

Bonilla last played during the 2001 season. Every July 1, MLB fans join together to celebrate "Bobby Bonilla Day," the special holiday they coined for the slugging third baseman. It's the day when the Mets pay their annual deferred fee to Bonilla.

#4. Yoenis Cespedes

Cespedes signed a four-year, $110 million contract extension with the Mets in 2016. While he was a star when he signed the deal, he quickly faded out of the league. Injuries and a COVID-19 opt-out limited his playing time. Cespedes played in just 127 games on that contract.

#3. Rusney Castillo

Castillo was an international talent that excited many teams in 2014. He came out of Cuba and signed a seven-year, $72.5 million deal with the Boston Red Sox. Unfortunately, he was not as ready as many insiders believed he was.

Castillo was demoted to the minors in 2016 and never returned to the big leagues. He finished out his contract at the Triple-A level before fizzling out entirely.

#2. Chris Sale

Sale signed a five-year, $145 million contract with the Red Sox in 2019. He was one of MLB's most dominant pitchers at the time and spent the last two seasons in Boston with great success.

However, shortly after signing the contract, Sale found it hard to stay on the field. He has been impacted by Tommy John surgery, a stress fracture in the ribs, a fractured finger, and a broken wrist.

#1. Stephen Strasburg

Strasburg's tale is a tough one. He was one of MLB's best pitchers in the league, especially during the 2019 season. He tallied an impressive 18 wins on 209 innings of work.

Following the 2019 MLB season, he signed a seven-year, $245 million contract with the Nationals. But since signing the deal, he has faced thoracic outlet syndrome, carpal tunnel surgery, and other ailments. Strasburg only threw 528 pitches after signing the deal and retired at the end of the 2023 season.