Leave it to Pete Alonso, the Baltimore Orioles and the New York Mets to make a relatively meaningless September series the talk of Major League Baseball.
Alonso’s return to Citi Field on Monday night, a 2-1 Orioles victory, officially eliminated the Mets from playoff contention. Baltimore still needs significant help to earn the AL’s final Wild Card seed, so all that did was keep their hopes alive for another night, as did Tuesday’s 11-inning win.
Mets fans have spent recent days making it clear how much they miss Alonso, who departed this past winter as the team’s all-time home run leader. Tuesday night presented us with Citi Field chanting Alonso’s name after he hit a game-tying, ninth-inning homer, almost as if they’d forgotten that he’d since left for the Charm City.
Alonso’s exit stings, but where does it rank among the Mets’ most painful moves? For this list, we’re focusing on players whose time in Queens realistically felt like it ended prematurely. As a result, we’re not including retirements or those who left when, for lack of phrasing, their time had come.
In other words, Mike Piazza signing with the Padres in 2006 didn’t crack our rankings; he was entering his age-37 season and the Mets were fully transitioning into the José Reyes and David Wright era.
5. Jacob deGrom signs with Rangers (December 2022)
Of all the players on this list, deGrom’s departure is arguably the one that felt the most inevitable. Plenty of Mets fans went into last winter genuinely believing that they’d re-sign Alonso, even after he made it clear upon the season’s end that he planned to test the free agent market.
However, deGrom was a 34-year-old coming off two injury-shortened seasons, and he wanted a massive payday. The Rangers were more than happy to follow through, giving him a five-year, $185 million contract. Elbow problems cost him most of the 2023 and 2024 seasons, but he’s been a rotation mainstay the last two years.
4. Trading Pete Crow-Armstrong to the Cubs (July 2021)
There have been many terrible moves by the Mets in the 21st century, but the Javier Báez trade is shaping up to be atop the list. Not only was the All-Star shortstop an awful fit in New York, but the Mets sent Crow-Armstrong to the Cubs for a rental player. Cohen and then-lead baseball executive Zack Scott are likely shaking their heads in disgust and regret most nights.
Báez’s time in New York is arguably best remembered for mocking Mets fans by turning his thumbs down. As for PCA, he’s increased his bWAR to 9.2 with 10 games left, and he’s only three stolen bases away from joining the 40-40 club. Great job, Mets.
3. Pete Alonso signs with Orioles (December 2025)
No need to repeat much of what we’ve said in recent days, but we leave you with this thought. Losing Alonso in free agency always would have hurt, though it may have been slightly easier to stomach knowing that the Mets at least made him an offer. As a ‘90s kid who grew up a Yankees fan, that’s how I felt when Robinson Canó left for the Mariners following the 2013 season.
But the Mets never seemed to have much interest in Alonso's market this winter. It’s no wonder why the fans showed him so much love this week, and why we expect that to be the case when the Orioles return to Citi Field in 2028 — assuming, of course, that he’s still with Baltimore and these two don’t meet in next year’s World Series.
2. Darryl Strawberry signs with Dodgers (November 1990)
Strawberry ranks above Alonso for two key reasons, the first being that he was a far more dominant player in his prime. If you’re unfamiliar with Strawberry’s story, he’s one of the greatest No. 1 picks in league history — his 42.2 bWAR ranks ninth among players taken atop the draft since its inception in 1965 — and among the most celebrated New York athletes of the 1980s.
A sweet-swinging lefty with big-time power and speed, Strawberry won 1983 NL Rookie of the Year, made seven straight All-Star teams (technically eight, counting his first year in Los Angeles) and helped the Mets to a 1986 championship. He was well on his way to the Hall of Fame when his contract expired following the 1990 season.
Strawberry signed a five-year, $22.5 million contract with the Dodgers, though injuries and substance abuse issues derailed the next few years. He again rose to prominence with the crosstown Yankees, winning three World Series rings during the Core Four years.
Thankfully, Strawberry has been sober for over two decades, and the Mets retired his No. 18 in 2024.
1. Tom Seaver traded to Reds (June 1977)
Next year marks 50 years since the “Midnight Massacre,” so make sure you check on any Mets fans who are old enough to remember June 15, 1977. The two-time defending champion Reds sent four players — Doug Flynn, Steve Henderson, Dan Norman and Pat Zachry — to the Mets for Seaver, who'd won nearly 200 games and two Cy Young Awards to that point.
In 2026 terms, imagine rolling over to check your phone and seeing that the Dodgers acquired Aaron Judge.
The trade shouldn’t have been overly surprising, given that Seaver had been feuding with management over his salary. He famously demanded a trade following a New York Daily News column suggesting that his wife, Nancy, was jealous that Angels pitcher Nolan Ryan — a former teammate of Seaver’s and a close friend — made more money.
Seaver wasn’t the only Met dealt that night, as outfielder Dave Kingman was sent to the Padres and shortstop Mike Phillips joined the Cardinals.
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