The Yankees may be the most decorated franchise in MLB with 27 World Series titles, but their history isn’t without brutal misfortunes. We are talking trades and big-money decisions. The most recent one, of course, was in 2023, when outfielder Josh Reddick questioned: How do you give someone $325 million without ever throwing a pitch in MLB? That was about Yoshinobu Yamamoto, right as the bidding war was heating up.

Reportedly, the Yankees did make a strong push, putting $300 million on the table. But they refused to go past Gerrit Cole’s $324 million contract out of principle… Brian Cashman didn’t want to top that number for someone who hadn’t thrown a single MLB pitch. A few months later, Yamamoto signed with the Dodgers for 12 years and $325 million, and then went on to win the 2025 World Series MVP. Now, with fans tearing into the Yankees for blowing that opportunity, another brutal reminder has popped up.

“The Yankees are lucky they didn’t get him [Shohei Ohtani],” sports radio legend Mike Francesa said back in 2018 after the Yankees lost out on Ohtani’s bidding to the Angels. Well, that did not age well.

Notably, in 2018, Ohtani entered the MLB with a 2.52 ERA, a 1.08 WHIP, and 624 strikeouts over 543 innings across five seasons in NPB. On the other hand, he had a .286/.358/.500 slash line with 48 HRs and 166 RBIs in 403 games and 1,035 at-bats over the same timeframe.

He was a worthy prospect, and Cashman knew that. Not only had Ohtani first caught their attention all the way back in 2012, but Cashman and assistant GM Jean Afterman had even flown down to Sapporo and Tokyo to attend his games before he entered the MLB market.

So they entered the bidding war, made an excellent presentation, and even got Hideki Matsui involved to help in recruitment. But as aforementioned, call it a Yankees’ misfortune.

According to Cashman, Ohtani was neither looking to settle in the East nor was he looking to join a big market franchise. So you could say the Yankees had lost the race even before it began. It sure stings now. This week, he earned his fourth MVP honor, trailing only Barry Bonds, while also tying David Ortiz for the most consecutive Designated Hitter Awards– five years in a row.

Their luck wasn’t much different with Yamamoto. By a few accounts, they placed forward a better deal than LA– $30 million AAV to the Dodgers’ $27 million, and opt-out after five years as opposed to the Dodgers’ six. Including a posting fee of $46.875 million to his Japanese club, Cashman & Co. were ready to spend about $200 million over five years on him. But it seemed like the West Coast was a lot more appealing.

Maybe the Yankees, being the most valuable team in the league, could have pushed for an undeniable offer. But here they are, while the Dodgers continue to reap the benefits.

So, given their World Series drought since 2009, their trade decisions need an overhaul.

The Yankees are facing the same situation with another Japanese talent, again

Shohei Ohtani, Yoshinobu Yamamoto, and Roki Sasaki are already off the Dodgers’ radar, and now the next big name from Japan could be Munetaka Murakami. For the unversed, his power is no joke… Notably, he smashed 56 home runs with a .710 slugging percentage in NPB back in 2022. Some people are even calling him the next Shohei Ohtani.

And guess what, the Yankees are once again in the mix, giving them a real shot to rebuild their reputation when it comes to landing Japanese stars. But right on cue, the debate has started about whether Murakami even fits in New York. MLB insider Ryan Garcia pointed out an unpopular stat comparison:
“Murakami’s Contact%: 63.9%. Giancarlo Stanton’s: 65.1%. And the average NPB fastball is more than 1 mph slower than the MLB average. How is this a ‘big bat’?”

Sure, those numbers raise eyebrows, but Murakami hasn’t taken a single MLB at-bat yet. Remember Ohtani’s early days in 2018? His first impressions didn’t predict the superstar he’d become. So this might be the moment for the Yankees to take the gamble, or risk watching Murakami turn into another one that got away.

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