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Will Hal Steinbrenner open checkbook wider in pursuit of Yankees' first World Series title since 2009?

Yankees managing general partner Hal Steinbrenner weighed in

Yankees managing general partner Hal Steinbrenner weighed in on Brian Cashman's contract, Carlos Correa, Aaron Judge and more during the MLB owners meetings in Chicago. Credit: AP/John Raoux

Debating the merits of bringing back Aaron Boone, as the Yankees officially did Tuesday with a new three-year deal, isn’t really that meaningful a conversation in the big picture.

As Brian Cashman pointed out, the club’s power brokers view Boone more as part of the solution than the problem, and that’s fine.

But the relationship that’s going to carry the Yankees to the World Series for the first time since 2009 isn’t the link between Boone and Cashman, which has been rock-solid chummy from the jump. It’s the one involving Cashman and Hal Steinbrenner’s checkbook.

The biggest strength of the Yankees has always been money and their willingness to buy success when possible. That’s nothing to be ashamed of. Maybe the Rays wear their small-market, tight-spending tenacity as a badge of honor, but the reality is Tampa Bay has been to two World Series since the franchise’s birth in 1998 and lost both.

This year, the Rays advanced one round further than the Yankees and were beaten by the Red Sox, same as their Bronx pals. It cost them only around $70 million — as compared with $207 million for the Yankees — so you can see where Steinbrenner might get a little frustrated.

But if the Yankees are going to be satisfied with the same people in charge trying to end the franchise’s 12-year World Series drought, where is the real change going to happen? For as much as we hear that Steinbrenner is all-in for the pursuit of No. 28 — a commitment that Cashman hammered again Tuesday — the Yankees seemed equally obsessed with staying under the luxury-tax threshold this season, which stood at $210 million.

Steinbrenner stated years ago that he didn’t believe the Yankees had to spend more than $200 million to win a title (maybe tack on a few more million these days to adjust for inflation). But he twice went above $230 million (on paper) in consecutive years, first with the trade for Giancarlo Stanton and then the signing of Gerrit Cole to a record nine-year, $324 million deal.

The pandemic prevented the Yankees from getting dinged by any tax for 2020 — the payroll tab for the shortened 60-game schedule was only $83 million — but Steinbrenner was mindful of staying below this year to avoid going over three seasons in a row, which triggers a 50% tax on the amount exceeding the line (for example, $10 million over results in a $5 million tax).

Once you reach those numbers, it doesn’t seem like much. Not until you get above $237 million, when a team’s top draft pick is affected. That still hasn’t stopped the Dodgers from shelling out $267 million for their ’21 club, which currently is down 2-1 to Atlanta in the NLCS.

Steinbrenner has been mindful of trimming tax whenever possible, and that included Cashman’s payroll-neutral trades for Joey Gallo and Anthony Rizzo at this season’s deadline. Does that sound like all-in from the owner? Cashman maintains yes.

"This man and his family are dedicated to delivering a successful team on a year-in, year-out basis with the belief that it at least has a chance to compete and win a World Series," Cashman said. "At the same time, they have an obligation to their investors to run the business in a sound way that doesn’t put any of that in jeopardy . . . That’s a balancing act."

Cashman suggested the Dodgers are a "unicorn" in the way they aggressively outspend the rest of the league. And just for the record, last year’s championship was L.A.’s first since 1988. Steinbrenner has invested roughly $2.4 billion in the Yankees’ title pursuit since the ’09 championship — not counting the tax bill — and has never made it back, totaling nine playoff appearances, with four trips to the ALCS.

Could throwing more money at the problem end that futility? There's no guarantee that it will, obviously. And with the current CBA expiring on Dec. 1, we don’t have any idea yet of what the new luxury-tax penalties will look like. For that reason, Cashman doesn’t know his ’22 budget parameters heading into a very uncertain winter.

The GM did say Tuesday that the entire roster needs to be re-evaluated and that his handiwork clearly wasn’t good enough this past season. Cashman accepted the blame for just about everything during his 67-minute Zoom call with the media, and with only a year left on his contract, it’s fair to say his job should be on the line if the Yankees are a disappointment again.

Because Cashman is treated more like a part of the owner's family than an employee, you could see Steinbrenner spending big this offseason to try and protect him. The team’s financial muscle has always been the Yankees’ best weapon, and they’ll need to flex it again this offseason.

"As a team and as an organization, we must grow, evolve and improve," Steinbrenner said Tuesday in a statement. "We need to get better. Period."

In terms of reaching that goal, his checkbook is going to help significantly more than merely having Boone in the dugout again.

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