Hal Steinbrenner’s Interview With Michael Kay Reveals What’s Wrong With The Yankees

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YES Network’s Michael Kay brought on Chairman of the New York Yankees Hal Steinbrenner to discuss the future of the team. He initially comes across as honest, mentioning disappointment for its postseason exist and also revealing that pay cuts could happen next year. It’s obvious that Hal’s business-like perspective doesn’t compare to those of his father George, so maybe it’s time to lower our expectations.

Here are words that never came out the mouth of George Steinbrenner or other past Yankee leaders: “We failed in that endeavor. Does that mean the whole season was a failure? No.”

How does he figure? In New York, winning the World Series is the only measuring stick. Fans in this city accept absolutely no consolation prizes and don’t give a rip about front office Yankee suits trying to run a business. New Yorkers are the reason that the franchise is lucrative, sometimes traveling all the way to the West Coast to watch their team win. This type of fan base doesn’t grow on trees. It’s built from the ground up.

The Yankees haven’t won the World Series since 2009 and even though George Steinbrenner passed away the year before, his fingerprints were all over their last winner. His philosophy has proven itself, guiding the Yankees to titles in ’96, ’98, ’99, ’00, losing in Game 7 in ’01 and in ’04 up 3-0 in the American League Championship Series.

Winning the World Series is still the Yankee expectation. Imagine having the same goal for over 10 years and failing to achieve it every single year. Now your boss gets on the radio in front of millions to say how great you are. Though that would never happen in your job, there’s a reason it’s happening with the Yankees and why Hal remains content with GM Brian Cashman.

The real goal

George Steinbrenner’s goal was to win the World Series. Anything else was considered a failure. Fans still agree, and Mr. November Derek Jeter echoes this idea all the time.

Jeter doesn’t care about quarterly revenue or regular season wins. His fixation on winning the World Series has been passed down to him by his boss. A Michael Jordan-like hatred of losing is the only way you can be loved by Yankee fans. This is why New York had no problem embracing Jeter or George’s “sore loser” sound when they failed. The city felt the exact same way.

Gerrit Cole became a Yankee last offseason on a 9-year, $324 million deal, and everyone predicted that Hal’s business mentality would be out the door. They were wrong. COVID took away fan attendance, the biggest source of Yankee income, and then Hal showed his true intentions: he wants to use COVID losses as a path for sympathy to make payroll cuts in 2021.

Signing the most expensive pitcher in baseball history feels like a PR stunt today. They spend a lot all at once so they could butter us up to spend less on the back end. They have bought a million dollar house, only to discover they can’t afford to run the AC in June.

Hal was asked about the future of AL batting champion DJ LeMahieu.

New York City will riot in the streets if LeMahieu doesn’t return. He has been the Yankees’ best player for two years. Hal can’t gawk over him too hard, or he risks running up the price tag even further. DJL is expected to reel in close to $100 million. We expect Hal to get it done.

What are they doing?

We now have to make predictions about whether or not the best player on the team will return. Why haven’t the Yankees signed a deal to keep DJL? Why would any major market team risk losing its best player to free agency? Answer: the Yankees are bracing for flexibility rather than looking to win.

There’s a big difference between trying to win and insisting on it. Even manager Aaron Boone stuck his tail between his legs after they were eliminated in the ALDS.

Boone was hired because he didn’t gauge Yankee success based on winning alone. He was hired to help the team compete, just as Hal’s business model requires. Boone fielded a team that won just enough regular season games to put butts in the seats. This method of making money has nothing to do with winning a World Series title.

Hal Steinbrenner wants to build regular season teams that have a puncher’s chance in the postseason. That’s all it takes to get fans fired up.

George never tried to fool fans out of their money. He was honest about wanting to win. He also had love for the team. He would hate this exchange of pennants for profits. Pay cuts from the New York Yankees are on the way, and fans shouldn’t let his son Hal off the hook.

Written by Gary Sheffield, Jr

Gary Sheffield Jr is the son of should-be MLB Hall of Famer, Gary Sheffield. He covers basketball and baseball for OutKick.com, chats with the Purple and Gold faithful on LakersNation, and shitposts on Twitter. You can follow him at GarySheffieldJr


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  1. Loved it when George was still alive and Billy Martin was coaching i mean all the drama firing and rehiring so entertaining and funny. Seen the Yanks play the Dodgers at Dodger Stadium when Billy and Tommy Lasorda for the Dodgers and Reggie Jackson was greeting fans along first base line prior to start really a great time.

  2. This is right on the money. Say what you will about old George–Gary Sr. probably has plenty to say–but if there was a disappointing result like this to a small market team, he would’ve been in his office with his staff THE NEXT DAY planning to retool his roster and do whatever it took to win. And probably chewing many people’s backsides in the process.

    Hank can’t sit still–Steve Cohen has billions to spend to make the Mets a contender.

    I’m reminded of John Helyar, in “The Lords of the Realm” quoting Reggie Jackson about his courtship by the Boss in 1976 to sign with the Yankees:
    “He hustled me like a broad.”

    Looks like Hank needs some business Viagra right now.

  3. There’s a reason why Derek Jeter is a legend and he still has the Winners mindset. I’m not a Yankees fan or cheerleader, however, I always respected Mr. George Steinbrenner for always wanting to win, money be damned.

    One of the best owners across all sports.

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