Meet the Dad With a Flawless Belly Flop

The humble belly flop is actually an athletic marvel combining daring courage, brutish savagery, and Bugs Bunny-level physical comedy. It requires a person to expose one of their softest, most vulnerable areas of their body to a walloping sting, all for a few laughs. Phil Di Ruggiero, a 46-year-old father of two, understands the pain and the pleasure of the belly flop on a deep, almost molecular level.

The scene: Rock Creek Pool in suburban Maryland, just outside of Washington, DC. Fourth of July, the pool absolutely buzzing with anticipation. Pie-eating contests, barbecues, and swim races dot the calendar, but the main event is the belly flop competitions, one for participants 12 and under, and the other for anyone 13 and up. After entering the adult contest two years ago and falling short of the gold medal (for real, the winner gets a gold medal), Di Ruggiero devised a plan.

“I did ask the judges in advance what they were looking for,” Di Ruggiero admits today. “Was it amplitude or form? And all three of them said form, form, form, which is really key. It’s a little counterintuitive. Most of the other people in my age division were doing enormous [attempts where you] jump as high as you can and then try to do something coming down. And I just really tried to focus on sticking to the concept of: man walks to the end of the diving board and rotates in.”

The result? An epic flop in which Di Ruggiero stuck a hand in his pocket, stared directly toward the judges—a group of three pool employees who rate each attempt on a scale of 1 to 10, slam dunk contest-style—and cemented his place in Rock Creek Pool history. While this is not a sport in the traditional sense—it’s more of an ESPN the Ocho type deal—Di Ruggiero honed his craft much like an athlete would: Reviewing the tape in search of paths to improvement, deceiving the opponent (during the warmup round, he did not do a single belly flop, so as to not reveal his genius ploy), and concocting a specific game plan.

“If you do an amazing one the first time and then you miss the mark on the second, you’re out because they go with the cumulative score,” Di Ruggiero, who received a score of 58 out of 60, explains. “So getting two triples is better than a home run and a single in this sense. I looked at all that and really, it’s an almost beautiful, put-together plan. I did anticipate nobody might be as strategic as I was with it.”

Di Ruggiero, a real estate advisor with Engel & Völkers in DC, has now had over a month to reflect on his achievement. His two daughters, ages 10 and 12, were both at camp when their father put his body on the line to bring home the medal. They’ve seen the videos, of course, and they have some thoughts. “The 12-year-old is now starting to consider some of the potential shame from having a goofy dad, while the younger one just finds it hilarious,” Di Ruggiero says with a chuckle. “Why did you do that, daddy? You’ll understand some day, kiddo. The thing that I keep coming back to is the reality that I could never have done this as a 14 or 15-year-old. I never would’ve had the chops to do it. But there’s something about the grace you get at midlife.”