In the New York Yankees' long and venerable franchise history, they've earned 27 World Series titles, a pile of hardware the rest of the league is still looking way up at, even after a down few decades.
Therefore, MLB's other 29 teams can't summon an ounce of pity for the game-changing acquisitions and free agent additions the Yankees almost made over the years, but instead narrowly missed on.
These near-misses stick out most during the 2017-present "empty" era without a title. Yankees whiffed on a free agent in 1993? Alright, well ... we know it all worked out for them. Yankees miss on a number of acquisitions that could've pushed them over the edge while the Baby Bombers were still on their rookie deals? Yeah. Those still sting.
Considering the stakes and the details, these near-misses stand out in recent Yankees history. Some of these deals you'll be glad the Yanks never completed, but others could've changed the franchise's trajectory for the better (and could've prevented the Astros from doing big things).
HONORABLE MENTION: When Zack Greinke went to the Astros at the buzzer at the 2019 trade deadline, which robbed the Yankees of their best chance of upgrading their roster and saw the Bombers lose out to a rival ... yet again. That said, from what we know of Greinke, he was never coming here, and wouldn't have prospered.
15 near-misses in free agency and trade market that could've changed Yankees history
Marcus Stroman Trade, 2019
The only thing Marcus Stroman being traded to the Yankees in 2019 absolutely could've prevented was a whole mess of Twitter blocking. If a Stroman-Yankees trade had been completed, there would be plenty more Bronx Bomber fans freely @ing Stro Show to this day and engaging in pleasant conversation.
Alas ... it was not to be.
Stroman was heavily rumored to be a Yankee in 2019, entering the deadline with a 2.96 ERA in Toronto, with just 99 Ks in 124.2 innings pitched. Instead, Brian Cashman found the price too high, famously stating that he "didn't think [Stroman] would be a difference-maker," and that he envisioned him in the Yankees' bullpen come October.
Stroman did not take this well. Rumor has it he threw a tantrum in the locker room when he learned he was "coming home" to the Mets and not the Yankees, and he has continued to attack the Bombers on Twitter to this day as pitching-weak.
Stroman went 4-2 with a 3.77 ERA that August and September for the Mets, allowing more hits (65) than innings pitched (59.2).