Two state-ranked teams in 2002 and 2003 entered the Sectional playoffs with lofty aspirations, only to suffer back-to-back semifinal flameouts.
It was DeGennaro who implored his son to play instinctively.
"He always told me, I'm not going to be the most athletic or the tallest player out there, but I can certainly be the most cerebral," Nick DeGennaro said.
"He emphasized being a smarter player, working on the parts I can control. I know I'm not going to beat anyone going 100 miles per hour, so the focus is on slowing it down, changing gears, and seeing the court."
Helping push DeGennaro's ascension has been Mike DeMello, a senior guard at White Plains.
DeMello spent the summer hanging with top-tier AAU programs with the House of Sports program. They two train together during the off-season.
DeMello, whose high-pressure trapping and shooting paced team Hudson Valley in the BCANY tournament this summer, took on a bulk of the scoring for Spencer Mayfield's Tigers this past season.
The seasoned guard will have immediate help from Jordan Tucker, a Class of 2017 forward who's already receiving interest from Oklahoma, Fordham, and Providence.
"DeMello is one of the smartest guys I've ever played with," said DeGennaro.
"He knows the game so, so well."
With a summer schedule revolving around hoops, DeGennaro had the opportunity to expand his offensive repertoire.
He's become more adept at taking the ball to the rim.
A tournament at Gun Hill Road in the Bronx, where a souped-up, run-and-drive brand of play is executed, helped accelerate the change.
The sophomore entered the tournament on a patchwork team, assembled at the 11th hour, with minimal expectations. He exited having earned a measure of street credit in a hostile hood setting.
"It is definitely a different environment," DeGennaro said.
"The basket is double rimmed and extremely bent, so basically the whole game is guys taking the ball to the rim, driving. Nobody is settling for the jumper, everyone is attacking the basket."