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The Yankees need to go all-in this winter

The Yankees might not be presented with an easier opportunity to re-tool than right now.

Major League Baseball London Announcement - Regent Street Cinema Photo by Kirsty O’Connor/PA Images via Getty Images

I hate the offseason. The endless stream of free agent speculation feels like circular logic at best, and I end up wasting what little free time I have reading into every rumor put out there. I become convinced that the Yankees are in on everyone, and am left disappointed when it turns out that they’re in on, say, Andrew Heaney. And, at the end of the offseason, with spring training looming on the horizon, I’m usually left thinking, that’s it?

Well, I’m happy to announce that I am here to contribute yet another piece to the circular logic of the offseason that I just mentioned! Yesterday I wrote a piece about all of the factors, both internal and external, that could convince the Yankees front office to stand pat this offseason. And, not to toot my own horn, but there are a lot of factors that could force the Yankees to do just that.

Today is a new day, however, and I’m here to argue that these factors should not preclude the Yankees, the richest franchise in the sport, from making serious splashes this offseason.

Let’s begin with the payroll situation I brought up yesterday. As just about every user on this site has pointed out at one point or another, the Yankees are the wealthiest team in baseball. Yes, their $211,000,000 estimated payroll going into the 2022 season is quite high — the next highest estimate is, naturally, the Dodgers, at $190,000,000 — but, again, this is the single wealthiest franchise in the sport; a sport that has no actual salary cap, by the way. There is no actual reason (no, I don’t consider Hal Steinbrenner’s frugality to be an actual reason) that this organization cannot afford to add multiple contracts this offseason. Next!

The CBA negotiations are definitely going to be a prickly thorn this offseason. As Esteban pointed out yesterday, there doesn’t seem to be any positive signs coming out of the talks so far. That complicates things for sure. But a work stoppage should not influence whether an organization is going to sign someone to a contract or not. Here’s a thought experiment: Team X gives Carlos Correa a 10-year, $300,000,000 contract in, say, two weeks. A new CBA is not reached, so a work stoppage goes into effect, which threatens to either shorten or cancel the 2022 season entirely. Does it suck that the organization is effectively paying Correa for one year despite the fact that he’s not able to play? Sure, I guess. But, at the end of the day, the team still has Correa for nine more years. As with any big free agent acquisition of this nature, an organization is not signing a guy for one year, they’re signing him for now and the future. If it comes to it, swallow the money now so you can still be good later. That doesn’t seem like a massive leap in logic, does it?

The second internal factor that I mentioned in my article was the looming extension of Aaron Judge. I’m going to break this down into two parts: (1) Judge deserves an extension, and (2) this extension should not factor into the way the Yankees spend this offseason. Since the start of the 2017 season, Judge ranks fifth in home runs, fourth in OPS, fourth in wOBA, third in wRC+, ninth in WPA, and fourth in WAR. The only names consistently above him in those categories include Mike Trout, Fernando Tatís Jr., and Juan Soto. Case number one closed.

As for case number two, have I mentioned that the Yankees are the wealthiest team in the league? Okay, I’ll skip talking about that again, but any discussion of Judge’s extension brings us to a whole new point: 2023. In yesterday’s article, I mentioned that the Yankees have a few big salaries — notably Aroldis Chapman, Zack Britton, and Joey Gallo — coming off the books, allowing them a bit more flexibility with their self-imposed cap. Given that this is his last year of arbitration, Judge would also hit free agency in 2023. Knowing that this flexibility is coming should incentivize the organization to give Judge the extension he deserves after moves are made this offseason. Take the tax hit now and reset in 2023, if you must.

However, knowing that this added flexibility is on the horizon might also make the Yankees consider passing on the 2022 free agent class in favor of re-tooling in 2023. Doing so would be a monumentally bad decision. For starters, the 2022 free agent class is ridiculously loaded. But, beyond just this season, the 2023 class does not look good. Aside from Nolan Arenado, Xander Bogaerts, and Jacob DeGrom — who would (tragically) be quite a risk to sign long-term at 33 after coming off multiple seasons with arm injuries — the most notable players are a trio of 36-year-olds in JD Martinez, José Abreu, and Justin Upton. Needless to say, I don’t think this team needs any more veterans approaching retirement.

As it stands, there is no better time than now — internal and external factors and all — for the Yankees to get better. If they are serious about bringing in a 28th World Series title to New York, this is the offseason to go big.