After six years away from ice hockey, former New York Islanders goalie and Massachusetts native Rick DiPietro made his return to the rink in 2019.
Although his playing days are behind him, DiPietro began his first season as a coach, leading the Portledge School boys varsity ice hockey team.
The new role was something he had been considering for a few years, and he believed he could share his experience and knowledge from his hockey days to his players. What he didn’t realize is just how much he would enjoy himself.
“I knew I’d like it, but I didn’t know how much I’d like it,” he said. “I think the biggest adjustment was trying to manage my regular job and being infatuated with trying to find ways to get my team better. I loved every second of it. … I wished I could do the coaching thing full time. There’s so much you feel you can do and want to do.”
DiPietro grew up in Winthrop, Mass., and had a stellar freshman season at Boston University. He was named to the Hockey East All-Rookie Team and second-team All-Hockey East, was MVP of the Beanpot, and put on a show in the NCAA tournament, stopping 77 out of 80 shots in a quadruple-overtime loss to St. Lawrence University.
After that one year at BU, DiPietro was selected first overall by the New York Islanders in 2000, becoming the first goalie to be taken with the first pick in the history of the NHL Entry Draft; he also was only the fourth American to be selected with the top pick.
DiPietro made his debut with the Islanders in the 2000-01 season, but he cemented himself as the team’s starting goaltender during the 2003-04 season. In the three seasons from 2005 through 2008, DiPietro played in more than 60 games and posted save percentages of at least 90 percent each year.
In 2006-07, he posted a 2.58 goals-against average and career-best .919 save percentage. He was selected as an NHL All-Star in 2008 and was Team USA’s starting goaltender in the 2006 Winter Olympics.
Persistent injuries hindered DiPietro over the next few years, as he played more than 20 games in a season just once before retiring in 2013 after getting cut by the AHL’s Charlotte Checkers after five seasons.
Quickly after his playing career ended, however, DiPietro began his new career in sports radio. Currently, he is a co-host on the “DiPietro, Cant, and Rothenberg” show on ESPN New York 98.7 FM. Coaching, however, had been on his mind.
The opportunity to begin that journey came through his 4-year-old son, who goes to school at Portledge School, a pre-nursery through grade 12 school in Locust Valley, N.Y. DiPietro said the administration was looking to “jump-start” the program and offered him the position.
“I really like the age group,” he said. “I go back into my own career and some of the coaches I had and look back at Jeff Jackson and credit him with a lot of my success. You can have a real impact on kids this age. My nephew is a sophomore in high school. Getting a chance to work with him, I just thought for my first year of coaching it was a good age group to get in with.
“My wife, I give her credit,” he added. “She’s the one that gave me the nudge I needed. I talked about potentially doing it. She said, ‘This is the perfect opportunity. Your son goes to school here. It’s the age group you want to work with.’ Getting to know the kids and their parents and where they come from, I fell in love with it.”
According to a 2010 article in Newsday, the program began in the early 1980s. A number of players went on to play ice hockey collegiately, and four players — Douglas Murray, Ryan Vesce, Eric Nystrom and Sonny Milano — emerged from Portledge to play in the NHL.
When DiPietro was selected by the Islanders in 2000, he said he vowed to be a Long Islander. Twenty years later, the New York Jets and New York Mets fan wanted to help grow the hockey scene on Long Island.
“I’ve been on Long Island almost 20 years now,” he said. “From the day I got here to now, it’s amazing to see how the hockey has grown. It was known for lacrosse. Now, there’s been so many kids from Long Island that played in the NHL. It’s tough to see the talent from Long Island go to different places. I want to keep that talent on Long Island. I moved away from my house at 15 years old. It was tough on me and tough on my parents. That’s what I want this thing to get to.”
The players on the team knew about DiPietro’s career and were excited to be coached by a former Islander, but he also knew that was only going to take him so far as a head coach. He called a number of his former coaches asking for advice, and he realized what all his favorite coaches did was not only develop him as a hockey player but helped him grow as a young man.
That was reiterated through interviews he did on his radio show with former New York Jets head coach Rex Ryan and former Jets general manager Mike Tannenbaum.
“Rex said, ‘Players don’t care how much you know until they know how much you care,’ ” DiPietro said. “That stuck with me. It was that fatherly relationship. You knew how much they cared about you, so they were willing to accept the criticism. I wanted the kids to know it wasn’t about me. It was about them and trying to get them to where they wanted to go. The biggest thing for me was everybody has to be all in. It has to be about we and not me. That was the message.”
The season began in thrilling fashion as the team topped Christian Brothers Academy, 2-1, in overtime.
Although that game earned DiPietro his first victory as head coach, the game he remembered most was the seventh game of the season, against Princeton Day School.
“Vitali Levy, one of our juniors, he tweaked his ankle,” he said. “I thought he was done. He takes his skate off. One of my seniors gives him the tape off his shin pad to tape his ankle. He makes an unbelievable pass in overtime to our defenseman to score the game-winner.
“Myself and the coaching staff and leaders, we spent a large chunk of the beginning of the season preaching team and everyone being all in and the sacrifice it takes to winning a championship, embracing a role,” DiPietro added. “To, in that moment, have a senior not playing a lot realize how important it was to have the guy get back on the ice, that was everything I was teaching them: being selfless, team first and doing what it takes. They did it, and it ended up in a huge win for us.”
The team’s season ended on Feb. 12 in the MAHL semifinals, in a 6-2 loss to The Hill School. Portledge’s final record was 6-5-1.
Although the season didn’t end in euphoria, DiPietro said the reaction to the loss was something to be proud of, even if it was difficult.
“To get a chance to see how the kids reacted after the last game was devastating,” he said. “To see how upset they were was tough. First year coaching, going into a locker room with seniors who have hockey careers that may be over, it was tough, but I was proud. It proved how much they cared and how much they bought in.”
While he hopes the players learned from him this season, DiPietro said he learned a lot this year. He said he learned to allow his assistant coaches to do more instead of wanting to control everything, and he said he can improve on making in-game adjustments. For the future, he would like to see the school build its own rink, so he can have more time on-ice with the players.
At the end of the day, though, the biggest takeaway from DiPietro’s season with Portledge was how much he loved it.
“I really was honored and blessed to be able to be surrounded by such good kids,” he said. “I had unbelievable kids that made it easy to come in. They were coachable. They were respectful. They couldn’t have made my first year more enjoyable.”


