What transpired Friday in the prelude to a potential parting of the ways between the Yankees and Aaron Judge was the classic case of dumb and even dumber.

For Hal Steinbrenner to offer a seven-year $213 million ($30.5 AAV) extension to the 30-year Judge, who’s had only two fully healthy seasons with the Yankees and missed 156 games due to injuries since 2017, would more than qualify him for winning the One Dumb Owner distinction for this off-season.

But for Judge to reject that offer and gamble on having an MVP season in ‘22 to force the Yankees into giving him Mike Trout money was even dumber. And make no mistake, this negotiation from the start was all about Mike Trout — who himself has played only 90 games in the first three years of his $430 million extension — and his $36M AAV. As Judge continued to maintain to the Yankees, he honestly believes he is as good or a better player than Trout and intends to be paid accordingly. Only problem with that assessment is that Trout currently has three MVP awards to Judge’s none.

Steinbrenner got a hint that this was going to be a very difficult negotiation in the arbitration process last month when the Yankees’ filed at $17M, which represented one of the highest raises in arbitration history, and Judge countered at $21M, which would more than double his 2021 salary. The Yankees don’t often go to arbitration with their players, but when they do, they don’t compromise from their number and always win – which bodes ominously for this acrimony with Judge.

I’m told that a number of agents, when they saw the Yankee offer to Judge, were astounded Steinbrenner had elected to go that far out in both years and money. Certainly he had to know like all of these six- and seven-year deals to players in their 30s, the contract will eventually become an albatross. But Steinbrenner obviously didn’t care. Judge is a homegrown Yankee whom the team has heavily marketed as their franchise player and Steinbrenner loves him and was determined to lock him up.

Assuming Judge, as he’s vowed, now takes this into free agency after the season, he’d better have an MVP year — which is already potentially compromised if he fails to get vaccinated and has to miss nine games in Toronto against the Yankees’ chief AL East rival, the Blue Jays. And what if he doesn’t have that year? Does he really believe Steinbrenner will continue negotiating against himself and improve on what is already an offer no other club but the Yankees would be willing to make to him?

I doubt if Judge is much of a student of baseball history. However, if he should encounter an untimely early batting slump or some tightness in that dreaded oblique, he might want to take a look at the case of Juan Gonzales in 2000. Gonzales was also 30 and had already won two MVP awards when the Rangers traded him to the Tigers, who then sought to keep him out of free agency by offering him an eight-year/ $140M contract extension. Gonzalez rejected the offer, had an injury-plagued subpar year for Detroit in 2000, and wound up getting a puny one-year/ $10M free agent deal from the Indians. Four years later he was “Juan Gone” — as in out of baseball.

Meanwhile, it was interesting that, at the same time the Yankees were unable to come to agreement with Judge on an extension, the Red Sox reached an impasse with their own homegrown mainstay, 29-year-old shortstop Xavier Bogaerts. The difference is, as Hal Steinbrenner clearly demonstrated he wants to keep Judge a Yankee, the Red Sox seem perfectly content to let Bogaerts opt out of his three-year/ $60M contract and walk at the end of the season — starting with their signing of Trevor Story for six years/ $140M this offseason. It wouldn’t be the first time the Sox parted ways with a star player who they deemed had gotten too expensive (see Jon Lester in 2014 and the Mookie Betts trade in 2020), but other than trying hard to lock up 25-year old third baseman Rafael Devers, the Red Sox are operating on the loyalty-be-damned analytics credo of no long term contracts for players in their 30s.

Being as the Yankees under Brian Cashman are married to analytics as much as any other team in baseball, it says even more that Hal Steinbrenner proposed to extend Judge to age 38 with the second highest AAV in baseball. In addressing the media after Friday’s game, Judge said: “I’m just disappointed because I have been vocal about wanting to be a Yankee for life.” This, after walking away from $230 million, which would have done just that. Please.

IT’S A MADD, MADD WORLD

Speaking of players who rejected multi-million extensions, do you think Carlos Correa, who reportedly turned down a 10-year/ $275M offer from the Tigers prior to the lockout, realizes he has to pay two agents for their services this winter? Back in January, there was a report in the Athletic that William Morris Endeavor Agency, which represented Correa, was in danger of losing their MLBPA certification because their purchase of a number of minor league teams, under the purview of a subsidiary organization Diamond Baseball Holdings, was a potential violation of union regulations which prohibit agents from having financial interests in professional baseball teams.

But according to a longtime union operative, these agent reprimand/sanction/decertification processes are always kept in-house and always resolved privately without ever being made public. No one knows how it got out but by sheer coincidence, a week after the Athletic report, Correa fired his Endeavor agent and hired Scott Boras, who eventually got him a three-year/ $105M deal with the Twins.

Nevertheless, it is stipulated Correa will have to pay both Boras and Endeavor — whose issue with the union is still unresolved — the same 5% commission for all the work they did for him … Between their multi million deal with DraftKings, the launch of “Pregame Spread” betting tips daily studio show on MLB network last week, and the posting of the “money lines” on their bottom of the screen of their TV broadcasts, isn’t it about time baseball ended this hypocrisy about gambling on baseball and allow Pete Rose to be eligible for the Hall of Fame? I mean, they welcomed two-time convicted steroid cheat Alex Rodriguez, who sued them, back into their good graces as the face of one of their network TV partners, and gave a pass to all of the sign-stealing cheating Astros. C’mon! Rose has long since paid his due for his transgressions. Let a Veterans Committee of his peers decide his fate — especially now in context with how baseball has done a complete turnaround in regard to gambling.

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