Can Yankees be trusted to spend their way out of current roster mess?

The fans want the Yankees to spend, spend spend. But can they do it right?
Feb 19, 2021; Tampa, Florida, USA; New York Yankees general manager Brian Cashman and owner Hal
Feb 19, 2021; Tampa, Florida, USA; New York Yankees general manager Brian Cashman and owner Hal / Kim Klement-USA TODAY Sports

The one unique advantage the New York Yankees have over the rest of MLB (or at least most of it) is that they can spend their way out of trouble. There's enough fiscal power in the Bronx to right as many wrongs as Hal Steinbrenner would like. It's just a matter of him signing off on them and stomaching the risk.

But that's not something the organization has done in recent years. They cut payroll after the 2017 and 2018 seasons -- you know, the two full-season showings that made it clear this team was a piece away from getting back the top of the mountain.

They traded for Giancarlo Stanton's $325 million contract instead of waiting an offseason for Bryce Harper and Manny Machado. Or -- hear us out -- they could've signed one of them alongside the Stanton trade a year later!

Even their "wins" in importing Gerrit Cole and re-signing Aaron Judge had their question marks. The Yankees paid $324 million for Cole and seemingly out-bid themselves by a lot of money after reports surfaced about the next highest bidder, the LA Angels, offering the right-hander an eight-year deal south of $300 million (and with deferrals). The Dodgers reportedly made a similar offer.

And then there's Judge, who the Yankees attempted to lowball before the 2022 season with a $213.5 million extension. Brian Cashman decided to leak that news moments before Opening Day to kill the vibes, Judge went on to hit an AL-record 62 home runs, and the Yankees were then forced to pay $360 million. All of that could've potentially been avoided had the Yankees offered at least $275 million.

Can Yankees be trusted to spend their way out of current roster mess?

The last spending spree approved by Hal ever since he took over after his father's death? Masahiro Tanaka (win), Brian McCann (dud), Jacoby Ellsbury (God help us) and Carlos Beltran (fine). That got the Yankees nowhere and actually contributed to their lifeless play from 2014-2016.

Much like the present day, the Yankees did not use their spending power to fix any of those poor decisions. In fact, they traded McCann to the Astros and played a role in kickstarting Houston's dynasty (that move helped them win the 2017 World Series). They traded Beltran to the Rangers for pitchers they never used. They had a public dispute with Ellsbury to get out of paying the remainder of his contract, which served as a distraction for years.

Who did they add from the end of the 2017 season until last offseason? They traded for Stanton, a move that's failed. They signed Cole, a move that was 10000% essential or else this team might've flatlined by now. They extended Aaron Hicks after one good season. They signed DJ LeMahieu on a bargain deal for 2019 and 2020, but then got suckered into giving him $90 million in what's become another sunk cost. They paid Aroldis Chapman, Zack Britton and Adam Ottavino far too much money. They have not paid for a single impact starting pitcher or bat over this span, unless you want to count a mid-level investment in an aging Anthony Rizzo or when they set fire to $50 million by trading for Josh Donaldson.

So, yes, the prospect of trading for Juan Soto and signing two of Cody Bellinger, Yoshinobu Yamamoto and Blake Snell sounds great, but do the Yankees even have recent experience in doing so much heavy lifting across one offseason over the last decade? You mean to tell us that after 10 years since their biggest spending spree, they're going to seamlessly come up with a five-prospect trade package for Soto and then be able to out-bid multiple other teams in free agency that have better spending power because of more flexible payrolls on two of the best talents in a free agency class that is top heavy?

We sure hope so. But this is the official warning we're issuing in the event we're delivered another letdown heading into 2024. And not only that, but there's plenty of heavy roster lifting to do after adding two of those above names. Everyone can't stand Cashman, but he's now entrusted to remake an 82-80 roster?