MLB insiders believe this trade deadline could become a seller’s dream originally appeared on The Sporting News.
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Parity was supposed to make baseball more competitive. According to Buster Olney, it may also create chaos at the trade deadline.
In his latest ESPN trade deadline preview, Olney described an American League landscape where almost nobody is fully out of the playoff race. That sounds exciting for fans, but it could create a brutal market for contenders desperate to improve.
The result? A potential seller’s dream.
Too many buyers, not enough stars available
Olney pointed directly to teams like the Boston Red Sox and Baltimore Orioles as examples of clubs stuck in the middle. Boston has struggled offensively for weeks and already made a managerial change, yet remains within striking distance of a playoff spot. Baltimore has underperformed badly, but is still hanging around the wild-card picture.
That creates hesitation. Teams a few games out in late May rarely want to wave the white flag, especially when expanded playoff races keep fanbases engaged longer than ever. According to Olney, rival executives already believe there may be far more “adders” than true “dealers” this summer.
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That imbalance could send prices soaring.
Front offices are preparing for aggressive bidding wars
Olney also highlighted several executives known for pushing aggressively at the deadline. A.J. Preller has never been shy about blockbuster moves. David Dombrowski already showed last year he is willing to move top prospects for bullpen help. Jerry Dipoto and Friedman were also mentioned among the sport’s most aggressive dealmakers.
When those kinds of executives enter a market with limited supply, things escalate quickly. That is especially true if elite names like Skubal actually become available.
The Rays may be the most fascinating team of all
Perhaps the most interesting twist in Olney’s reporting involves the Tampa Bay Rays. Entering the season, many around baseball expected Tampa Bay to sell pieces at the deadline. Instead, the Rays suddenly own the best record in the American League and could pivot aggressively into buyer mode.
Olney noted rival executives believe Tampa Bay has both the assets and front-office creativity to pursue major upgrades despite operating as a smaller-market franchise. That could make this deadline unlike most recent years. Instead of obvious sellers flooding the market, baseball may be heading toward a frenzy where nearly every contender is fighting over the same handful of impact players.
The six early X factors defining this year’s MLB trade deadline.
Breaking down the themes that will shape the 2026 deadline and the teams that could be a part of it.https://t.co/lX1OHYQuro— Buster Olney (@Buster_ESPN) May 22, 2026
And that is exactly how bidding wars start.
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