If there was one thing that my dad, the late Island attorney and Vineyard advocate Ron Rappaport, loved as much as he loved his family, it was basketball.
Don’t fact check this claim, though, he also really loved the Island community, his friends, a cold beer on a hot day, a swim at Lucy Vincent beach and reading a newspaper, among other things.
When he was a boy, he used to pretend he’d gone to bed, then listen to Celtics (and Red Sox) games on a radio under the blankets. He played in high school (not necessarily successfully). And the evening before he died he reveled in a game at TD Garden that contained, in his words spoken to me by phone the next morning: “The best seven minutes of basketball I’ve ever seen — ever!”
And every year Dad would spend days obsessively researching college basketball teams and players to craft an impeccable and often unbeatable March Madness bracket.
I did not inherit this love of the game, which he shared with my mom, but it did rub off a bit. For my seventh or eighth birthday I blew out the candles wishing that Larry Bird’s back would make a miraculous recovery in time for the finals. I loved going to games with my dad — from college matches to pro games at the Garden. And as a young adult, I started entering brackets, too, choosing blindly or with a little bit of input from my dad:“help me fill out my march madness bracket!” (email to him dated February 13, 2014).
Last week, as March settled into its dreary middle, the invitations to fill out brackets started rolling in. But, since his death in 2024, I just couldn’t bring myself to enter one — playing the same game that I once played with him, the same people still in it, just my dad missing. It was a reminder of the game he loved, and the fact that I want more than anything for these little moments to still be taken for granted: the asks for assistance on putting together my picks, the emails the morning after games had reshuffled the leaderboard: “Go Jack! Go Jules!” (from him to me and my husband, dated March 19, 2018), or the moments of gloating: “How is my buddy doing? Also I’m in 2nd place in my office NCAA pool.” (sent to me by text on March 24, 2019).
As I sat on the couch feeling sad, my husband filled out his brackets.
“You know,” he said, pausing on his picks. “Of all the approaches there are to filling out a bracket, your dad’s was my favorite.”
“What was his approach?” I asked.
“Well, he played to win,” Jack said. “But at his office, he used the winnings to take everyone out for a round of drinks, on him. Imagine being a business owner playing March Madness and you either win, and take money from all your employees, or you have to try to lose!”
It was so like Dad, figuring out a way that he could both win, and have as much fun with everyone involved as possible, while also making everyone feel good about it.
And he did, in fact, always seem to win, according to Paul Moreau, his colleague at Reynolds, Rappaport, Kaplan & Hackney, who also confirmed that Dad bought everyone drinks with the pool money.
“We joked that it was rigged, every year he won,” Moreau told me, noting that the buy-in to play is $10 and usually about 20 to 25 people enter.
He remembered how Dad was all consumed by the games and the brackets, and kept everyone’s position in the rankings stored in his head.
“He’d be walking up the stairs and would turn back to offer an aside like, ‘Duke won last night,’” Moreau said. And you would know it was either because Dad had picked Duke to win — or because he remembered that you had picked them to lose.
And while there are no brackets for me this year, just as there weren’t last year, these memories and anecdotes lift me up, as do the words of encouragement and humor from my dad that I sifted through while writing this. But what I wouldn’t give to be getting them now — the joy something akin to watching a three-pointer shot from downtown swish through the net as the buzzer goes off. Something like that, but even sweeter.
Julia Rappaport lives in Newton and Chilmark.
This article appears in March 27, 2026.

Wonderful wonderful Julia. A happily obsessed sports parent truly sets one on a raft of memories that float by with clips of the season. Basically your team won.
Thank you Julia for sharing this wonderful story and part of Ron’s passion. I wonder if he would have picked UCONN this year. Only the best to you and your family.
Please go back to filling brackets!
Julia,
What a great memory of your Dad. I can attest to his hoops obsession. Every call we had over the many years of friendship seemed to have a puck my brain segment on the Celtics’ future or the sleeper teams in the Tournament. Like you, what I wouldn’t give to get one more of those calls.