Ken Rosenthal drastically misses the mark in Brian Cashman Yankees assessment

New York Yankees fans are frustrated. It's been 17 long years since they've enjoyed a parade down the Canyon of Heroes following a World Series victory. The man primarily responsible for that frustration is general manager Brian Cashman.

If you ask veteran MLB insider Ken Rosenthal, though, Cashman is doing a bang-up job. Rosenthal gushed about Cashman during a recent appearance on Foul Territory.

"It's time, it's past time, to understand what [Brian] Cashman has accomplished," Rosenthal said. "And all of those years finishing above .500, since 1998, yes, they have had financial advantages, too. So have a lot of other teams. No other team has had a winning record every year.

"Now I know, certain fans, certain Yankees fans, will say, 'No World Series title since 2009.' Yes, that is true. It's undeniable, and some of the teams have not been constructed as well as they could've been. I would expect Cashman would say that as well. However, they are always in the mix."

He went on to acknowledge what the standard is in New York - World Series or bust - and he detailed that through line from George Steinbrenner to Derek Jeter to Aaron Judge. But ultimately, his point was that the playoffs are random and that Cashman shouldn't be held accountable for not winning a ring since 2009. Regular season greatness, in Rosenthal's opinion, is a better measuring stick of a GM's abilities.

Sounds ridiculous, right? Even if we grant him that the World Series is tough to win, and it is, that's the point! We're still looking at a clear decline. Think back to the dynasty that began in 1996. The Yankees won four World Series, yes, but they had also lost two others (2001, 2003), meaning that during an eight-year stretch they made it to the final showdown six times. Now consider that since 2009 they only have one World Series appearance to their credit: the 2024 defeat at the hands of the Los Angeles Dodgers.

It's hard not to see a distinct break. Remember, too, that Cashman ascended to the role of general manager on February 3, 1998. He's not fully responsible for those championship clubs, as they had been molded and shaped by Gene Michael and Bob Watson before him.

Also remember that during the 2008-2009 offseason, Cashman's seat was scorching hot, and he was basically mandated by George to go on the huge spending spree that netted New York CC Sabathia, Mark Teixeira, and A.J. Burnett. If his hand hadn't been forced, we likely wouldn't have seen those splashes, and we don't have the ring to show for it.

An honest assessment of Brian Cashman's Yankees tenure pegs him as a middle-of-the-pack general manager

Going back to Rosenthal for a second, he's also been on an apology tour for Cincinnati Reds president of baseball operations, Nick Krall. Krall runs a small-market team, but he enjoys having an MVP-caliber player in Elly De La Cruz, a young ace in Chase Burns, and the likely NL Rookie of the Year in Sal Stewart on pre-arb contracts. That trio makes up just under $2.5 million of Cincinnati's $133 million payroll. He could've set the remaining $130 million on fire and gotten better results.

I bring this up as a reminder that insiders like Rosenthal's sole job is to get inside information and break stories. They get that by cultivating relationships, so when you hear them give an edgy or unconventional opinion, it's because they don't want to hurt a source's feelings.

This isn't to say that Cashman is a bad GM. He's made his share of great moves. He's made blockbuster trades like acquiring Alex Rodriguez, Giancarlo Stanton, and Juan Soto. He's found diamonds in the rough like Brent Headrick (and several others).

But the issue with Cashman is that he doesn't learn from his past mistakes. After failing to acquire prime Johan Santana to protect Phil Hughes, Joba Chamberlain, and Ian Kennedy, he let Ivan Nova, Eduardo Nunez, and Adam Warren stand in the way of trading for Cliff Lee a few years later. Then he compounded the mistake when he failed to sign Lee the following offseason.

In recent years, he's failed to capitalize on Aaron Judge being the literal reincarnation of Babe Ruth by shying away from emptying out the farm to acquire difference makers who would have changed the Yankees' calculus.

It's impossible to look at his missteps and not see titles left on the table. It's criminal that he's enjoyed the best hitter this generation has produced, yet since 2017 has just one World Series appearance to show for it.

Go back to the 1998 team. That should have been his lesson. That club laid waste to the American League, winning 114 games. Entering October, a World Series berth felt inevitable. Going into the World Series against the San Diego Padres, the only question was whether the Yankees would hoist the Commissioner's Trophy after four games or five.

Since those glory days, winning the division is no longer a guarantee. Making the playoffs has sometimes felt like it's on shaky ground. The standard has been lowered, but by the organization, not the fans.

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