Fanatics Fest: 27 Rings Discussion
- Paul Semendinger
- Jun 30
- 3 min read
by Paul Semendinger
June 30, 2025
***
Last weekend, Ethan and I attended the first day of Fanatics Fest in New York City as members of the media.
One very appealing aspect of Fanatics Fest were discussions with superstars in the large downstairs theater. We attended the "Only in New York: 27 Rings" event - one that brought Derek Jeter, Alex Rodriguez, C.C. Sabathia, Andy Pettitte, and Jorge Posada to the stage to discuss some of their perspectives on the Yankees championship success.
What follows are some highlights from the discussion:
The first question posed focused on what was it that allowed the Yankees to win so often in the 1990s.
Jorge Posada began by noting that the players on the stage, and the team, owed much of the success to Bernie Williams. Posada stated that Williams set the stage by coming through the minor league system and having big league success. The sentiment was that he paved the way for the other Yankee minor leaguers to follow. This idea was met with agreement from the panel.
Derek Jeter then added that it was George Steinbrenner's approach that gave the Yankees the best chance to win.
Jeter noted that Steinbrenner set the tone from the top down. Winning was expected. The players were taught to push themselves to be the best they could be.
Jorge Posada then noted that George Steinbrenner was always there for the players. He shared that Steinbrenner was the first person to write a check to Posada's charity foundation. He also said that Steinbrenner "taught us how to win." Posada noted that the Yankees back then had "a lot of rules," but that these rules and expectations helped them become a winning team and more. Posada added that George Steinbrenner, "helped us be the men we are today."
Later in the program, Derek Jeter went back to the higher standards the Yankees were held to - such a not having beards and having to wear suits on all flights. He noted that the team today keeps eliminating rules. (To this attendee, and writer, there seemed to be a messaage there that the Yankees won when they had higher standards in so many ways and they have not won as those rules have been relaxed.)
Andy Pettitte concurred with all of this noting that he showed the team how important it is to win. With a smile, he added, "If we didn't do our job he'll get rid of us" indicating that this help motivate the players to set high standards and expectations for themselves and their daily performance. In short, Pettitte added that Steinbrenner, "Gave us the drive to win."
The conversation moved into a discussion about each player's favorite World Series championship.
Derek Jeter began this by asking, with a laugh, if a parent can have a favorite child. He noted that they were all very special.
For Alex Rodriguez, there was only one title, 2009, so that one held very special meaning to him.
For Jorge Posada, all of the championships were special.
Andy Pettitte indicated that the 2009 World Series championship was the most special since it came after he returned to the team and after the had fallen short so many times previously.
The final interesting question came from a fan who asked the Yankees to share the best advice they could give.
Derek Jeter noted that everyone fails. It's not a matter of failing, it's a matter of working through the failure to find success.
Alex Rodriguez then stated that they Yankees had a very strong network of former stars who always seemed to be on hand to offer advice and support. Rodriguez specially named Roy White, Reggie Jackson, and Willie Randolph as leaders who guided the players.
In all, this was an extremely interesting and great discussion to attend. It was clear that the players still hold George Steinbrenner in high regard and credit his leadership as a critical and essential element for the Yankees' success in the 1990s and early 2000s.
I am sure there was good George and bad George as there is in all of us… He wanted to win no matter what it took…some results were disastrous some worked out…but the Yankees were always interesting with him at the helm …Can’t really say that with Hal in control.
I agree that Steinbrenner gave extensively to charity. That is a big plus in his corner.
His second big plus was getting banned for a few years for hiring a thug to "get dirt" on Dave Winfield with an eye to stiffing Winfield's charity on Steinbrenner's contractual obligation. That ban allowed Gene Michael to build a team with people like the Core Four, who more likely than not would have been traded for more useless veterans by a frantic Steinbrenner. Thank you for being such a huge sleaze, George; you really helped the team's long-term success that way.
The rest of the player hagiography of Steinbrenner is nauseating. "Derek Jeter then added that it was George Steinbrenner's approach that gav…
I envy your attendance. That must have been so much fun to watch.