The MLB free agency landscape is a double-edged sword, and sometimes, the biggest stories aren't about the players who sign, but the teams that miss out on their top targets. It's a delicate dance for front offices, navigating team needs, budget constraints, fan hopes, and countless other factors. And sometimes, they get it wrong, leaving them with contracts that become a heavy burden. Here are some of the most haunting free agency deals that are still weighing on MLB teams in 2026.
The Curse of the Unlucky Lefty: Eduardo Rodriguez's Arizona Nightmare
When the Arizona Diamondbacks signed Eduardo Rodriguez to a four-year, $80 million deal, it seemed like a steal. But Rodriguez's luck ran out, and he missed most of the 2024 season due to injuries. Despite a fuller workload in 2025, his ERA and WHIP were underwhelming. Rodriguez's age and declining velocity suggest his prime is behind him, leaving Arizona with a hefty contract and a questionable future for their pitching staff.
But here's where it gets controversial: Rodriguez's hard-hit rate was encouraging, suggesting he might still have something left. Is it time to give up on him, or could he be a valuable asset if given the right opportunities?
The All-Star Turned Albatross: Anthony Rendon's Angelic Nightmare
Anthony Rendon, once an All-Star with the Washington Nationals, signed a seven-year, $245 million contract with the Los Angeles Angels in 2020. However, Rendon's contract has become a financial burden, preventing the Angels from making a real impact in the postseason race. The recent restructuring of his deal, spreading $38 million over five years, hasn't led to significant spending elsewhere, leaving the Angels treading water.
And this is the part most people miss: Rendon's contract has been a huge disappointment, but is it fair to blame him for the Angels' struggles? Or should the front office take responsibility for their failed investment?
The Blue Jays' Missed Opportunity: Anthony Santander's Outfield Dilemma
Anthony Santander's five-year, $92.5 million contract with the Toronto Blue Jays looks worse than it is, but it's still a concern. After a poor debut season, Santander's contract is a reminder of Toronto's near-miss with Kyle Tucker, who signed with the Dodgers instead. The Blue Jays have had a string of close calls with top free agents, including Shohei Ohtani and Juan Soto.
But Santander's contract is a complex issue. He's tied up an outfield spot for four years, and his performance has been inconsistent. With Tucker dominating in L.A., Blue Jays fans might be left wondering what could have been.
The Japanese Import's Struggle: Masataka Yoshida's Boston Bind
The Boston Red Sox signed Masataka Yoshida to a five-year, $90 million contract, but his bat has been in a constant decline since his strong rookie season. Yoshida's injuries and limited power have left Boston with a real problem, especially with a surplus of outfielders. Trading away young talent like Jarren Duran or Wilyer Abreu doesn't solve the issue, as both hit more effectively than Yoshida.
Boston's attempts to improve through free agency, like their pursuit of Alex Bregman and their investment in Ranger Suárez, have been impacted by Yoshida's contract. It's a complicating factor that the Red Sox would love to undo.
The Long-Term Commitment: Xander Bogaerts' San Diego Stint
The San Diego Padres have had a quiet offseason, and their hands are tied due to ownership disputes and a depleted farm system. The Xander Bogaerts contract, an 11-year, $280 million deal, has become a negative inflection point. Bogaerts is still a good player, but his age and offensive decline are concerns.
The Padres will be paying Bogaerts over $25 million in his age-40 season, and this contract is already hindering their ability to add younger talent. It's a long-term commitment that might become a burden as Bogaerts ages.
The Reunited Astros: Carlos Correa's Houston Dilemma
The Houston Astros reunited with Carlos Correa at the 2025 trade deadline, but now they're stuck with a costly contract. Correa is beloved in Houston, but he's too expensive to trade, and his age and declining consistency are concerns. The Astros might have to consider trading All-Star third baseman Isaac Paredes, who outperformed Correa in 2025.
Correa's contract is forcing the Astros to make tough decisions, benching or trading younger, more productive players. It's a situation that has left the front office's reputation in question.
The Broken Promise: Aaron Nola's Philadelphia Complication
The Philadelphia Phillies gave Aaron Nola a seven-year, $172 million extension, but Nola's performance in 2025 was disappointing. The Phillies might now regret their decision, as Nola's contract is a huge complication. It potentially prevented them from going after bigger targets like Bo Bichette and has impacted their ability to retain key players like Ranger Suárez.
Philadelphia's rotation is now a source of uncertainty, with the Zack Wheeler injury and the departure of Suárez. The Nola contract is a reminder that sometimes, even the best intentions can lead to unexpected challenges.
