Several Former Cubs with “Ugliest Contracts in MLB”

The Athletic just published an article ($$$) with the ugliest contracts in Major League Baseball, and the list was littered with former Cubs including two from the 2016 World Series team.

Of the top 10, half once played for the Cubs, and another was a major free-agent target last off-season.

10. Tanner Scott (4-year, $72 million), Dodgers

The Cubs pursued Scott heavily last off-season, but were outbid by the Dodgers. and all their deferred money. Scott had a negative WAR in 2025, and did not pitch in the postseason for Los Angeles due to injury.

9. Yu Darvish (6-year, $108 million), Padres

Darvish, who was signed as the primary replacement for Jake Arrieta before the 2018 season, was traded to the Padres before 2021. It was seen as a cost cutting move, and a precursor to the tear-down that was coming that season. For the Cubs, Owen Caissie is the only asset remaining from the deal. https://www.espn.com/mlb/story/_/id/30615373/sources-san-diego-padres-set-acquire-yu-darvish-chicago-cubs

Darvish pitched well for the rest of the contract he had signed with the Cubs, with a 6.0 WAR over 2 seasons, including 3.10 ERA across 30 starts in 2022. The issue was that after the 6-year extension he signed, he has only a 2.8 WAR over 3 seasons, two of which were shortened by injury. And he will miss the entirety of 2026 due to elbow surgery.

8. Giancarlo Stanton (13-year, $325 million), Yankees

7. Javier Baez (6-year, $140 million), Tigers

This one hurts as Javy was one of my favorite Cubs ever. He was one of the 2016 heroes I was hoping could get an extension, but getting Pete Crow-Armstrong from the Mets softened the slow of his departure: https://www.espn.com/mlb/story/_/id/31922264/sources-new-york-mets-finalizing-deal-chicago-cubs-javier-baez

But Baez has struggled mightily for the Tigers, with a 3.9 WAR and a .626 OPS over 4 seasons. He seemed to be headed for a bounce back season in 2025, with a ,752 OPS in the first half. But his OPS cratered in the 2nd half to .548.

6. Nick Castellanos (5-year, $100 million), Phillies

Castellanos was a big pickup in 2019, and had an OPS over 1.000 in 51 games to close the season. https://www.espn.com/mlb/story?id=27298027&src=desktop

Many hoped he would re-sign, but instead he left to go to the Reds for 2 years and $30 million. His 34 homers in 2021 convinced the Phillies to give him his current deal, where he has accrued a miniscule 1.4 WAR over 4 seasons.

5. Joc Pederson (2-year, $37 million), Rangers

Pederson was not with the Cubs very long, playing in 73 games in 201 before being shipped to the Braves in the first of what would be many trades that season. He did well for Arizona in 2024, but was terrible for Texas last season.

4. Anthony Santander (5-year, $92.5 million), Blue Jays

3. Mike Trout (12-year, $426 million), Angels

Wow…Mike Trout is on this list? The Angels got lots of value in the first 7 years of the deal, but those time appear to be over. It’s a travesty that he has only 15 postseason plate appearances, all in 2015 in an ALDS loss to the Royals.

2. Anthony Rendon (7-year, $245 million), Angels

That there is only one year left in this contract is the only good thing to say about it. Rendon has a 3.9 WAR in his 5 seasons with the Angels, and sat out all of 2025.

1. Kris Bryant (7-year, $182 million), Rockies

Similar to Mark Prior 20 years earlier, Bryant was a phenom with the Cubs who had his career deeply impacted by injury. He was another Cubs that most of us were hoping would be locked up for his whole career. Instead he was traded for 2 prospects who did not work out. But, unfortunately, the real win for the Cubs was cutting ties with Bryant before signing him to a long-term deal. Maybe he’ll be able to make a comeback, but recent reports on his health are not very positive.

There was a whole video on the rise and fall of Baez and Bryant:
https://www.youtube.com/watch?v=LLogaLPY4pE

Ultimately, while many former Cubs appeared on this list, there were no current Cubs. And there were no Cubs among the nine honorable mentions. Since the Jason Heyward deal, the Cubs have seemingly avoided pursuing the biggest name free agents in each off-season. They gave fairly big deals to Dansby Swanson, Seiya Suzuki, Shota Imanaga and Matthew Boyd, but none were probably big enough to show up on this list, even if the players were failures. While it is admirable that the Cubs front office have avoided any major busts, it also reflects the safe approach they have taken to signing free agents.