It’s been over 30 years, but Isaac Fine still remembers the toughest moment of his tennis career like it was yesterday.

It was 1994. Fine, then a senior at Newton North, was a doubles player on the varsity tennis team. The Tigers had made it all the way to the state semifinals and were playing Amherst for a shot at the finals. With all other matches completed, the score stood at 2-2. The last match to be decided—the one that would determine who advanced and who did not—belonged to Fine and his partner.

In the third and deciding set, North had earned a match point. But when Fine’s opponent served the ball, everything fell apart.

“I remember it clearly, hitting that forehand return into the net,” recalls Fine. The match point was snuffed out. Soon, too, was Fine’s season, as Amherst put together a rally to win the match and advance to the state championship. That loss was the final match of Fine’s high school tennis career.

“I felt like I wanted to be playing in that deciding match, but to be in that position and not to be able to win and come through for your team was really difficult,” he says.

Decades later, the story has added a far happier chapter. On June 13, Fine watched his son Alex complete a come-from-behind singles victory in the state championship match against Newton South, giving the Tigers their first state tennis title in 24 years.

“Alex was able to redeem the family name,” says Fine. “It was very exciting but also very nerve-wracking.”

The younger Fine’s victory capped off a memorable day for North’s tennis team. The Tigers were a confident bunch coming into the match, having logged a regular-season victory over South as well as a thrilling come-from-behind win against Lexington in the state semifinals. But after the first two matches ended, North found themselves down 0-2, with no margin for error remaining.

“It was a different feeling on the court, seeing our team losing in that big match,” says Alex, a sophomore who plays third singles.

When the Tigers’ top two singles players won their matchups, all eyes turned to Alex’s court to see which school would emerge as state champions. In the third and deciding set, Alex fell behind 2-4 before running off four straight games, punctuating the victory with a powerful overhead slam on the final point. As the crowd roared, Alex fell to the ground and held his head in disbelief. North were champions.

“Winning that match was pretty surreal,” he said. “A really cool feeling.”

Isaac Fine hugs his son, Alex Fine, after a state championship victory on June 13, 2026. Courtesy photo

Alex admits that he thought about his father’s experience in the semifinals all those years ago throughout the match. For years, as the two played tennis together, he had heard the story of the return dumped into the net, followed by a dispiriting loss.

Would that be his story, too?

He determined that it would not be. Rather than focus on that negative outcome, Alex found a way to put a positive twist on the story to help him focus on what he needed to do.

“I think the lesson to learn there is—I didn’t want to think about what would have happened had I done that,” he says. “Given the fact that I’ve heard the story so many times it has to have been a pretty important memory, so I just wanted to make sure I knew the memory [from my match] would be really positive.”

Watching the match alongside hundreds of other spectators, Isaac was nervous—but not too surprised that his son turned up his game when the pressure began to build. He had seen him come back many times before, relying on an arsenal of shots as well as a strong mental game.

“It’s very hard to start to play your best game when things are tight, and that’s something I have seen in his tennis for many years,” says Isaac. After the celebrations had ended and the trophy had been awarded, Isaac joined Alex on the court. They embraced. Alex had achieved his dream of winning a state championship—not just for himself, but for his friends and teammates. And for Isaac, witnessing his son’s critical role in the championship match helped make the pain of his own loss in 1994 a bit easier to bear.

“It was an awesome day,” he says. “I was thinking about my experience, and it was just fun to have that connection with him and the team all those years later. So I enjoyed that very much. I’m very proud of him.”