ESPN’s Tom Rinaldi: A journey like few others; From teacher to TV interviewer on sports’ center stage

Buddy Hendershot picked Tom Rinaldi up from the airport. This was 1988. Hendershot had just hired Rinaldi as an English teacher at Shady Side Academy in suburban Pittsburgh, Pennsylvania. “Everyone was excited about him,” Hendershot recalls.

Hendershot took Rinaldi out to Dingbats, a now-closed restaurant. “It was almost as if I had known him for a while,” Hendershot says. “He was an easy conversationalist.”

Though Rinaldi was the new kid on the block, he had already influenced the man who hired him. As the head of the English department, Hendershot watched Rinaldi teach for the first couple of weeks. “He was not afraid to get in the face of the kids who thought they were just going to sit back,” Hendershot says. “That dynamic energy of his to interact with students is the hallmark [of a great teacher].”

Rinaldi wasn’t going to let his students slide on his watch. Shady Side was established in 1883 by the newly rich industrialists of Pittsburgh’s East End to provide an elite education for their sons. The Frick and Mellon families were among the Academy’s early patrons. Today it’s still a breeding ground for elite talent: alumni include Pulitzer Prize-winner David McCullough and astronaut Jay Apt. This is where Rinaldi chose to make an impact. 

Before Rinaldi became well-known for his direct and powerful one-on-one sit-down interviews and moving features as an ESPN correspondent, he was a teacher at two high schools for four years. Rinaldi’s illustrious journalism career has its roots in the world of teaching, where he made a profound impact on the wealthy and the decidedly not.

Rinaldi was born in Brooklyn and grew up with his older brother and sister in Cresskill, New Jersey. As a student, Rinaldi earned all A’s. He attended Fordham University for a year before transferring to the University of Pennsylvania. Between his junior and senior years at Penn, Rinaldi worked at a camp for gifted and talented children where he taught, mentored, and inspired. “I loved that experience, and I sort of thought perhaps I should teach,” Rinaldi says.

Though he never took any education classes in college, Rinaldi decided to apply for teaching positions. His first job was at Shady Side, where he earned the respect of his students. Hendershot called hiring Rinaldi a “no-brainer.”

Jeff Miller worked in the English department with Rinaldi from 1988 to 1990. One afternoon, Rinaldi approached Miller in the hallway. “Jeff, there are only the pursued, the pursuing, the busy and the tired,” Miller remembers Rinaldi quoting from a line in The Great Gatsby. Miller hadn’t thought about that line until Rinaldi reminded him of it. The two teachers bonded over books, like The Great Gatsby, and plays, like David Mamet’s Glengarry Glen Ross.

Miller says Rinaldi was special. “He was kind of in wonder of the world,” Miller says. “He was a really good listener, and he would ask really interesting questions. He really did care about hearing somebody else’s perspective.”

Rinaldi uses that curiosity and empathy in every one-on-one interview he conducts for ESPN. In Tiger Woods’ first interview after he crashed his car into a fire hydrant and tree, Rinaldi shows genuine inquisitiveness. Woods, explaining his part in a fight with his wife that would lead to divorce and public embarrassment, is humble and yielding – exactly what he is not on a golf course. Woods tries to look away for a moment, but Rinaldi’s demanding eyes bring him right back in.

When he interviews LSU head football coach Ed Orgeron after LSU’s win over Alabama, Rinaldi is unrelentingly focused. His eyes are locked on Orgeron, fixated and stone-like, revealing awe and respect. Even after Orgeron and Rinaldi share a raucous laugh, Rinaldi again draws him back in like a siren seducing a sailor.

Rinaldi wrote a book while at ESPN. But instead of covering a sports hero, he wrote about one of the most iconic, gut-wrenching moments in the country’s history. In The Red Bandanna, a New York Times bestseller, Rinaldi tells of the unknown Welles Crowther, a stock trader and volunteer firefighter who saved eighteen lives in the South Tower of the World Trade Center. Crowther died as the tower collapsed, still trying to save others. To further share the story of this unknown hero, Rinaldi wrote a young readers adaptation of his book. He instinctively recognized colossal courage, and he was going to make damn sure everyone knew who the man in the red bandana was.

A quick story to illuminate Rinaldi’s personality: At Shady Side, Rinaldi helped coach the ninth grade basketball Indians with head coach Gene Deal, the school’s athletic director. Rinaldi showed up to every practice rocking old-school red canvas Converse High Tops. Deal wondered: “who the heck is this guy?” But soon, Deal would witness the intense fire of Rinaldi as a coach and player.

The team had only nine players and needed one more to have a five-on-five scrimmage. Rinaldi became the tenth guy. “He was so damn competitive,” Deal remembers. “I used to have to pull him out of practice and say, ‘Hey, these are only freshmen, man. Leave them alone, you crazy man!’”

Rinaldi helped primarily with warmups, drills and defense, but he loved to scrimmage. “You go to the hoop, he’s kicking your ass, I’m telling you,” Deal says. “That’s just the way he was. He was so dadgum competitive when he got in a game. It was like, ‘hey, take a deep breath here, man. It’s okay.’”

Deal says the players loved Rinaldi’s fiery and caring personality. Bart Griffith Jr., the current President of Shady Side, was one of those players. “He had high expectations for us,” Griffith says. “A lot of times his intensity was equally focused on character education as it was on the execution of the basketball team. He did have another gear I think people probably don’t see in a lot of the highly sentimental, personal interest pieces he does for ESPN.”

Rinaldi connected with his players through a mixture of care and teasing that very few people have a good knack for, Griffith says. Rinaldi related with the players and cared about them as people beyond their function on the team.

Griffith remembers Rinaldi visiting Shady Side in 1990, after he left the school. Rinaldi came back to visit in the spring of Griffith’s senior year, a time when students were making college commitments. As Griffith walked toward the gymnasium, he ran into Rinaldi. The two were happy to reunite, and Griffith briefly shared his college choice dilemma with Rinaldi. “Let’s take a walk,” Rinaldi insisted.

The two went on a 30-minute walk through the beautiful back fields of Shady Side. Despite his recent departure, Rinaldi was still invested in his former student’s decision.

For a time, Griffith wanted to be the next Tom Rinaldi. He was deciding between the S.I. Newhouse School of Public Communications at Syracuse University and several other small liberal arts schools. While the small liberal arts schools weren’t going to have professional training as part of their curricula, Griffith was intrigued. Maybe, he thought, he could follow Rinaldi’s teaching career, rather than his broadcasting career.

On that walk, Rinaldi shared words that have stuck with Griffith his entire life. “Bart, I see you as someone highly interrelational, who enjoys the exchange of ideas that is a part of academic life, and who would be great as an adult around young people,” Rinaldi told him. “And while I certainly don’t want to make the decision for you, I’ve been in broadcast communications for only a year or two at this point, but I know relative to my teaching experience, it can be sort of solitary work. I would really encourage you to at least take your time and explore.”

Rinaldi encouraged Griffith to go to Bucknell University. Griffith talked to everyone about his college decision—parents, aunts, uncles and grandparents—but the conversation with Rinaldi was the most influential one. The next day, Griffith committed to Bucknell, where he majored in English and History.

Rinaldi left Shady Side for another challenge. He left a bastion of ease and comfort for a stockade of struggle and strife. A part of the inaugural class of Teach for America that year, Rinaldi wanted to teach high school students. But Teach for America could only place teachers in elementary or intermediate schools, so Rinaldi obtained emergency accreditation and was placed at Morris High School in the South Bronx, one of the poorest schools in New York.

When Rinaldi arrived at Morris, he sent a note back to his colleagues at Shady Side asking for help, Jeff Miller says. “These kids don’t have books or pencils or pens,” Miller remembers Rinaldi saying. Miller and other colleagues sent books, pencils, pens and notebooks.

For Rinaldi, teaching in an entity as massive as the New York City public school system was eye-opening, but he loved it and thought it was a tremendous experience.  “I really didn’t know what I didn’t know until I got there,” Rinaldi says. “I hadn’t known clients of social services. I hadn’t known people who had been involved in the criminal justice system. I hadn’t known poverty in that shape and fashion.”

Hendershot, who hired Rinaldi at Shady Side, says Rinaldi wanted to see what he could do with kids from different backgrounds, from places where kids were fighting to stay alive. “He wanted to see the whole experience of life, the haves and the have-nots and see how he could bring people up and how he could motivate people,” Hendershot says.

Motivate, he did. While there, Rinaldi coached handball, a game he loves. “We were the Morris Bulldogs, so I called us the Dogs of the Wall,” Rinaldi says. “I can’t profess that there’s a lot of great strategy that I was imparting, but I was the responsible adult, and I’m sure I had a much higher view of my motivational skills than the players did, but I loved to try to motivate.”

After teaching at Morris, Rinaldi headed to Columbia Journalism School, where he earned his master’s degree and then became a one-man-band in TV news.

Rinaldi’s first job in journalism was as a general news reporter at WNDU-TV in South Bend, Indiana. Maureen McFadden, a longtime anchor at the station, immediately noticed something about his work. “He was a fabulous writer,” McFadden says. “He was so far ahead of the kids who usually come in. I remember thinking, ‘I hope my kids grow up to be like this guy because he had so much empathy.’ He always listened to people and he was always fair and kind.”

Ellen Crooke was the news director who hired Rinaldi at WNDU-TV. Crooke says she doesn’t remember many other resume reels, but she remembers the feeling she had when she watched Rinaldi’s. “He was just out of [school], but he really had an old soul to him . . . like he had lived a million lives and understood humanity and understood how to tell the human condition in a way that I had really never seen, and I don’t know that I’ve seen it since,” Crooke says.  

Shady Side had the Indians. Morris High had the Dogs of the Wall. Rinaldi had experienced two different worlds. 

After three years at WNDU-TV, Rinaldi spent the next two years in Portland, Oregon. In 1998, Rinaldi entered the sports world, working for CNN/SI (Sports Illustrated) until 2002. In 2003, Rinaldi joined ESPN, where he became known for emotional, longform storytelling and powerful one-on-one interviews with some of the biggest stars in the sports world.

But it was the world of teaching that launched Rinaldi’s journalism career. “It helped me in terms of the awareness of needing to be clear in how to communicate,” Rinaldi, now 52, says. “I’d like to think it has taught me how to ask questions, how to listen to answers, and I also think it taught me to put a premium on curiosity.”