Anthony Rendon’s looming buyout and likely retirement punctuate a sobering reality for MLB: both of the 2019 Nationals’ post–World Series megadeals—for Rendon and Stephen Strasburg—have rapidly become two of the biggest financial whiffs in baseball history, reshaping how superstars and long-term contracts are seen by teams and fans alike.
When the Washington Nationals conquered baseball in 2019, the franchise faced an almost enviable but fateful dilemma: which superstar to pay. Four years later, buyout talks between Anthony Rendon and the Los Angeles Angels have ended the debate—not only did the Nationals pick the wrong cornerstone, but both of their outgoing aces became emblematic of how lucrative, long-term contracts can go disastrously wrong for everyone involved.
The Backstory: From World Champions to Mega-Contracts
After capturing their first World Series title in October 2019, the Nationals needed to choose between two franchise icons: third baseman Anthony Rendon and pitcher Stephen Strasburg. Both were in their prime, coming off career-defining seasons, and both were poised for massive paydays. Washington’s decision ended in two parallel, record-tying deals—Strasburg re-signed with the Nationals for seven years and $245 million, and Rendon signed an identical deal with the Angels just days later. The question today isn’t who the Nats should have chosen, but whether they should have chosen either at all.
The magnitude of these contracts reflected the teams’ confidence in proven production—Rendon had slashed an elite .319/.412/.598 with a league-leading 126 RBI, while Strasburg posted a dominant 209 innings on the mound, sealing his World Series MVP case. Yet, as the baseball world is now forced to admit, these massive investments quickly devolved into write-offs with staggering opportunity costs for all parties involved.
A Brutal Financial Reckoning: Multimillion-Dollar Absences
News broke this week that the Angels and Anthony Rendon are deep in talks to buy out the final year of his contract, with Rendon likely to retire shortly after [ESPN]. The buyout news shocked few given Rendon’s prolonged absence due to injuries. Since his spectacular 2020 campaign (in a COVID-shortened season), Rendon managed just 205 games for the Angels across four years—hampered by an unending series of health setbacks, including season-ending hip, wrist, tibia, hamstring, and oblique ailments. The final tally for the Angels: $38 million owed for 2026, likely paid in full, and a lineup spot that never materialized into long-term value or leadership.
Strasburg’s story is even grimmer for the Nationals. After signing his new deal, Strasburg made only seven regular-season starts, struggling with severe injuries, most devastatingly thoracic outlet syndrome—a notoriously career-threatening diagnosis for pitchers. Ultimately, he retired after lengthy buyout negotiations [Yahoo Sports]. The Nationals paid nearly his entire $245 million contract for less than two months of subpar pitching, with reports indicating the deal was not insured, compounding the financial blow [Yahoo Sports].
The All-Time “Worst Contract” Debate—And the Numbers That Set Them Apart
The Rendon and Strasburg debacles aren’t merely anecdotal. When cross-referenced with Baseball Reference’s database of the largest contracts in MLB history, both deals now unequivocally rank among the bottom for return on investment—lower even, by some standards, than infamous deals like Chris Davis, Ryan Howard, or Josh Hamilton.
Just how rare is their collective fall-off? Of the 50 largest contracts in league history, only a handful have produced so little actual value. In terms of advanced metrics like Wins Above Replacement (WAR), Rendon and Strasburg both sit near the absolute bottom. Virtually every other superstar contract, even those regarded as disappointments, has delivered at least one standout season or year of on-field reliability. By contrast, these two deals provided teams with extended stretches of inactivity and, by extension, little hope for sunk cost recovery.
Comparing to Recent Deals: Bryant, Cabrera, and Beyond
While Kris Bryant and Miguel Cabrera are often cited as comparisons, the numbers and narratives are telling. Cabrera at least delivered one Silver Slugger-level year with Detroit and remains a Tigers icon. Bryant’s Rockies stint has been marred by injuries and position confusion; he’s played even fewer games since signing his megadeal but hasn’t publicly entertained retirement. Meanwhile, Rendon’s tepid attitude toward his baseball future and highly publicized clashes—such as stating baseball was not his “top priority” and his infamous altercations with fans and media—have colored the legacy of his contract [Yahoo Sports].
- Strasburg: Seven starts post-2019, 6.89 ERA, retired after full financial payout.
- Rendon: Played just 205 games over five seasons, frequent IL stints, production dropped off sharply after 2020.
- Bryant: Logged 128 games across three Rockies seasons, but has not yet retired, and continues to attempt comebacks.
This trio stands apart, not just for their price tags, but for failing to provide even short-term impact—cementing what it means for a contract to be “worst ever”
Franchise-Legacy Fallout and the Fan Conversation
For Nationals fans, the sting of these contracts is complicated. The 2019 title remains one of baseball’s great stories, but the financial hangover has lingered far beyond the parade. The franchise still faces a rebuild, unable to leverage their resources with flexibility, and haunted by “what if” scenarios: What if the Nats had gone younger, invested in depth, or let both stars walk?
For Angels fans, Rendon’s deal became symbolic of the team’s decade-long frustrations with roster construction, durability, and clubhouse leadership. In a market notorious for high-profile misses (see also: Josh Hamilton and Albert Pujols), Rendon’s tenure provided few highlights and more questions about the cost of chasing postseason relevance through free agency.
Lessons for MLB Front Offices and Future Superstars
These monumental contract busts will have ripple effects. MLB front offices are already shifting focus to performance-based structures, deeper medical evaluations, and risk-sharing contracts. Fans, meanwhile, are savvier and more skeptical of megadeals, especially for players approaching or just past peak production—wondering aloud if every new $200-million deal might spell disaster.
The 2019 Nationals’ story is a powerful reminder: even a World Series title can’t always justify the long-term cost of rewarding postseason heroes. Rendon and Strasburg’s deals will be debated every offseason as teams weigh risk versus reward in superstar free agency and fans dissect every front office move on social media. Ultimately, these contracts will stand as case studies of what can go wrong when the championship window collides with a superstar payday.
For instant, authoritative baseball analysis as soon as news breaks, keep your browser locked to onlytrustedinfo.com—your top home for smart, fast, and comprehensive MLB coverage that cuts through the noise.
