There’s no arguing the Yankees are the most decorated franchise in MLB with 27 World Series titles. But their history isn’t without brutal missteps, especially in trades and big-money decisions. Take what former Yankees outfielder Josh Reddick said back in 2023: “How do you give a guy $325 million without ever throwing a pitch in MLB?” He was talking about Yoshinobu Yamamoto, right as the bidding war for him 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, an old Shohei Ohtani clip has resurfaced, only adding fuel to the frustration.

“The Yankees are lucky they didn’t get Ohtani,” sports radio legend Mike Francesa said back in 2018 after the Yankees lost out on Ohtani’s bidding to the Angels.

Yes, you heard that right. Someone actually said that not landing Ohtani is a lucky thing for a team. Well, yes, that time Ohtani was a new name in the MLB circuit, and no one had the idea about what was coming next. Typical of the big-market teams like the Yankees, investing huge in an unknown prospect was not recommended.

However, Ohtani’s NPB career should have been focused more. 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. So why not invest in such talent?

The Yankees thought it would be a losing bet to invest heavily in an unknown talent, as they didn’t do with Yamamoto. Result? The Dodgers eventually had their hands on both of them and are now reaping the results.

So, apart from the Yankees’ 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.