Yoshinobu Yamamoto signed a $325 million contract with the Los Angeles Dodgers prior to the 2024 season. In the end, the Dodgers' ties to Japan – and their willingness to bid higher than their competitors for an unproven starting pitcher – won the day. Yamamoto was untested in major-league terms when he signed long-term in Los Angeles, but those who scouted him in Japan (and the Dodgers were not alone on that front) knew exactly what he could become. That all came to fruition in Game 2 of the World Series on Saturday night.
Yamamoto pitched a complete game against the Blue Jays, giving up just four hits and one run. It was his second complete game of this postseason, and he retired the final 20 hitters he faced. On a pitching staff which features Blake Snell, Tyler Glasnow, Roki Sasaki and (at times) Shohei Ohtani, it's tough to argue anyone is pitching as well as Yamamoto these days.
The Dodgers were far from the only team interested in Yamamoto back in the winter of 2023-24. The right-hander heard pitches from at least a half-dozen teams, some of which were stronger than others. After two solid seasons in the big leagues with subsequent World Series runs, sellers' remorse doesn't begin to describe the overwhelming feeling in front offices across baseball. How do the Dodgers keep getting away with this?
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Philadelphia Phillies
Dave Dombrowski has made plenty of high-profile moves since he signed on to become the Phillies president of baseball operations back in 2020. If there's one thing we know about Dombrowski, it's that he's not afraid to throw around ownership's money. In that sense, he's a great fit as a mouthpiece and front office actor for John Middleton, who isn't shy about spending said money.
The Phillies have one of the highest payrolls in baseball, but they could not compete with the international scouting infrastructure the Dodgers had at their disposal back in the winter of 2023-24. Philadelphia got a meeting with Yamamoto and his representation. Bryce Harper made a pitch to Yamamoto personally, hoping to sell the right-hander on Philadelphia's sports culture and the Phillies' championship pedigree. None of it was enough.
The Phillies aren't higher on this list because they've managed to build one of the better rotations in baseball without Yamamoto. Yet, the organization has fallen short of its goals ever since losing out on the Japanese phenom – losing in the NLDS the last two seasons running. Yamamoto could've been the piece to extend their World Series window. Instead, it's shutting and there's little Dombrowski can do to stop it.
Toronto Blue Jays
Yes, the AL pennant-winning Blue Jays make the cut as well. Toronto wasn't just shut down by Yamamoto on Saturday night, they also failed to make much of a pitch for his services in the first place. In an article from Dec. 2023, Kaitlyn McGrath argued adding a player like Yamamoto would not just aid the Blue Jays' strength at the time – their starting pitching – but also provide more relief for its sleeping giant of a lineup. She was not wrong. McGrath suggested that adding Yamamoto would've allowed the Blue Jays to trade from its stockpile of starting pitching and add to its position player pool. The logic is flawless, even though the Jays were able to prove much of their fanbase and national pundits wrong by making a World Series run in 2025.
Considering how close the Blue Jays got to signing Ohtani and Sasaki, who's to say Yamamoto wouldn't have taken them more seriously? We have to take timing into account when judging the Blue Jays pursuit of Yamamoto. This was just one winter removed from missing on Ohtani, and the Jays were hot in pursuit of another star to add to their war chest.
Hindsight is 20/20, and the Blue Jays sure would've rather started Yamamoto in Game 2 rather than have faced him. Had they pursued him more seriously, who knows what the end result would've been?
New York Mets
While they ultimately fell a few million short, Steve Cohen and David Stears were very invested in Yamamoto entering the 2023-24 offseason. Both men went to Japan to scout and meet Yamamoto in person during the NPB season. They established relationships with those close to him, including his agency, and none of it meant a damn in the end.
"I think the whole organization tried our hardest, and someone was going to win and someone was going to lose and that is the way it goes," Cohen told the New York Post after Yamamoto signed in LA. "I feel good about our efforts and I left it all on the field. Life goes on."
The Mets finished fourth in the NL East the previous season despite their $346 million payroll. While New York had to feel good about its farm system at the time, the rotation was a sore spot then and remains so to this day. If a few million was what came in the way of Yamamoto becoming the next Mets ace, it looks awfully silly given they signed Juan Soto to a $765 million deal the following winter.
New York Yankees
Ah, the Yankees. The payroll behemoths of yesteryear have shown themselves to be surprisingly cheap with top-tier free agents under the guidance of Hal Steinbrenner and Brian Cashman. The Yankees reportedly offered Yamamoto $300 million, and fell just short of the eventual $325 million deal he signed with the Los Angeles Dodgers.
The Yankees got creative with their offer, and their deal reportedly would've paid Yamamoto a higher AAV than what he signed in Los Angeles. If he was always partial to joining Ohtani with the Dodgers, then there's very little they could've done to sway him in another direction. That being said, what ultimately got in the way of giving Yamamoto the $325 million he desired was rather silly. Per Jon Heyman, the Yankees did not want to pay Yamamoto more than Gerrit Cole, whose deal was for $324 million over nine years, as Cole was the Yanks' ace. Cashman and Co. were nervous about how Cole would react to being the second-highest-paid starting pitcher on their payroll. Frankly, that's a problem to solve later.
Even had Cole been peeved by Yamamoto's deal, surely he would've gotten over it had the Yankees been in better position to win a World Series in 2024 and 2025. New York ran into Yamamoto's Dodgers in the 2024 Fall Classic, and fell short of their goal. This past season, Cole was injured, making New York's need for a pitcher of Yamamoto's quality all the more obvious.
This is a mistake the Yankees cannot take back.