Bill O'Sullivan, now a teacher at Eleanor Roosevelt High School...

Bill O'Sullivan, now a teacher at Eleanor Roosevelt High School in Manhattan, shows off his Yankees World Series Championship rings that he received during his time working in media relations for the team. Credit: Brittany Bernstein

Growing up in the Bronx, Bill O’Sullivan idolized Don Mattingly and dreamed of playing for the New York Yankees. In none of his dreams was he riding on a World Series parade float while fans threw things and chanted, “Who are you?”

But that’s what happened to O’Sullivan in 1998 when, as a media relations assistant for the Yankees, he found himself on a float with other non-recognizable staffers after the Yankees beat the San Diego Padres.

As a senior at St. John’s University in 1997, O’Sullivan had already known for a long time that donning the pinstripes wasn’t going to pan out. So, when the opportunity came to intern for the Yankees’ media relations department, he figured it was as close as he could get to making the Yankees’ roster.

After graduating with his bachelor's degree in athletic administration plus a year of interning under his belt, the Yankees promoted O’Sullivan to full-time media relations assistant.

“It was great … dealing with David Cone, Bernie Williams or Mariano [Rivera] or Derek Jeter,” he said. “It’s funny as you do this longer, they’re famous but they sort of just become normal people to you.”

O’Sullivan, now 44, worked for the Yankees during the team’s three consecutive world championships from 1998-2000.

“In 1998, when they won the World Series, that was [my] first time being part of something huge,” he said. “Just the craziness and being able to be on the field and being in the clubhouse, it was sort of like I was a player, but I was a meaningless person on the side.”

Some days O’Sullivan’s job included shaking hands with Michael Jordan, being on the field during DiMaggio Day while Paul Simon performed “Mrs. Robinson” and playing basketball with general manager Brian Cashman and members of the Bronx community at Macomb Dam Park during his lunch break.

But the job also had its challenges, including one O’Sullivan remembers involving the famously mercurial late Yankees owner George Steinbrenner.

When the head of media relations wasn’t on site at Spring Training in 1998 and Hideki Irabu threw a Japanese reporter’s camera on the ground, Steinbrenner was looking to speak to a media relations person.

“I’m a 20-something-year-old kid and the owner of this team, I always remember, said, ‘Young man, do you like your job?’”

When O’Sullivan replied, “Yes, sir,” Steinbrenner advised him to keep the Japanese media away from Irabu.

“I loved each and every single day there, it was great,” he said. “Then as we were going ... towards ... ‘99-2000 I knew I was going to be getting married I was trying to figure out what’s going to work best in the future to make sure I had time with my family.”

He first switched to working in sponsorship services for the Yankees, before ultimately leaving the organization in March of 2001, eight months before his wedding, to work at Madison Square Garden in client season ticket services. While working at MSG, he decided to pursue a career teaching health and physical education, and began taking classes at Hofstra. After almost two years of taking classes part-time, he left MSG to become a full-time student and got his master’s in 2005.

After working as a permanent substitute teacher for three years on Long Island, he turned to teaching in Manhattan and eventually found his current role at Eleanor Roosevelt High School on the Upper East Side in 2011. O’Sullivan, whose family moved to Nesconset when he was 7, now resides in Holbrook with his wife, Karen, and his daughters Sara, 12, and Sydney, 6.

Bill O'Sullivan worked for the Yankees during the team's three...

Bill O'Sullivan worked for the Yankees during the team's three consecutive world championships from 1998-2000, and has the rings to show for it. Credit: Brittany Bernstein

Even now, almost 20 years later, O’Sullivan’s time with the Yankees comes up often. He’ll bring his World Series rings into his health class and tell students about the lessons he learned in his time with the organization — including the PR staff’s missive to the players about building positive relationship with the media for their own good.

O’Sullivan has rings from the 1998 and 1999 World Series, but though he was still with the organization for its 2000 win, he left in November. The unwritten policy was that if you weren’t employed when the rings were given out, you didn’t get one, he said.

“It didn’t matter to me … I was just thankful for what I had already received,” he said.

When the team won in 1999, O’Sullivan was featured in a photo on the front page of the New York Daily News. After his first parade experience, he made sure to get on a better float — the one with Jeter. is talking to Long Island teachers who were in another career before going into education. Do you have a story to share about finding your way into the classroom? Send it to

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