Derek Jeter spent his professional career with the New York Yankees. He developed a special bond with billionaire team owner George Steinbrenner during that time. The Yankees’ former captain regularly spoke of the man at the helm with a lot of respect. But shortly after winning the 2009 World Series, he slated Steinbrenner for a particular trait. 

Jeter always respected Steinbrenner during his time with the Bombers despite the clashes they had on various issues. But the longtime Yankees’ captain once had some uncharacteristic criticism for the billionaire. 

Derek Jeter admitted that George Steinbrenner only cared about winning

Under George Steinbrenner, the Yankees experienced one of their most significant periods of success. This was due to his unwavering desire to win and maintain discipline. Derek Jeter understood the same desire and seemingly agreed with it. But in an interview with Sports Illustrated in 2010, he bluntly admitted that “The Boss” was obsessed with winning. 

According to Sports Illustrated, Jeter said, “We learned that coming up. The Boss [George Steinbrenner], all he cared about, was winning.” He admitted this while sitting with the other members of Core 4, Jorge Posada, Mariano Rivera, and Andy Pettitte. 

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But no matter his methods, Steinbrenner ensured his team was competitive. Furthermore, he oversaw an iconic Yankees era, personally getting involved with many aspects of it. His relationship with Jeter may have seen its rocky days, but he trusted the shortstop with the captaincy. The two honestly had a special bond, and Jeter paid tribute to the father figure after his demise. However, the latter had some issues with the former’s character traits. 

Jeter and The Boss clashed over partying

It is well documented that George Steinbrenner was not happy with how Derek Jeter sometimes partied. Although the Yankees’ former captain was dedicated to his craft, he occasionally enjoyed the nightlife. But his bachelor lifestyle seemed to displease The Boss.

Read More: Derek Jeter Once Tormented Billionaire Yankees Owner George Steinbrenner’s Son With Champagne to Keep Up Tradition

This was in particular during the late 90s and early 2000s. The 2003 things came to a head when Steinbrenner publicly talked about Jeter’s single lifestyle, which left the legendary shortstop angry. 

Derek Jeter and George Steinbrenner had a special bond despite the feud and disagreements. What do you think of the legendary Yankees’ shortstop’s comments about the divisive owner?

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