The foil fencer from Passirano, a small town near Brescia, has been fencing since he was five and competed at every single Olympic Games from Athens 2004 where he won team foil gold and individual bronze.
His contribution has helped keep Italy at the top of the world, the country has won more fencing Olympic, World, and European medals than anyone else.
But despite all fencing competition being put on pause until 2021, the three-time Olympic medallist is keeping busy.
36-year-old Cassara is staying sharp in the National Training Centre with sessions once a week, studying for a sport science degree at the University of Brescia, and enjoying some down time with his wife and his dog, Attila, who is very much part of the family.
Cassara has found a new passion too - teaching and coaching kids in the sport of foil fencing.
"I have more stress when I go to see the competition of my students," he laughs, speaking to Tokyo 2020.
His new love for teaching even rivals some of his greatest Olympic moments says Cassara.
"I can compare [coaching] with my career - it’s different but I can compare. There is a lot of emotion."
The world might feel a little crazy in times of Covid-19, but Cassara is staying calm, and keeping his sights firmly set on Tokyo 2020.
The Italian team have already secured their berth, which will see Cassarà appearing in his fifth Olympic Games. Adding to his team gold and individual boronze at Athens 2004, he was part of the fencing 'Dream Team' that took another gold in the team event in London 2012.
This heavily decorated fencer (17 World Cup golds, a World championship title, 11 Grand Prix golds), says he now knows how to handle pressure better and is more than ready for Tokyo.
"In Beijing 2008 and London 2012, especially in London, I had a lot of pressure because I was number one of the world. So all eyes were on me because 'it's your Games'. So we won in the team but I didn’t really perform very well in the individual [event]."
"Now I hope next year at 37 [years of age], in Tokyo I [will be] less stressed. I earned this Games. So I'm happy to go, then we will see what’s going to happen."
Cassara's chill attitude is partly a result of working with a mental coach, with whom he started working with after Rio 2016, especially after having doubts about continuing with fencing.
Part of what he learned is to enjoy the process more than the outcome and getting a better sense of his emotions amidst victories and even failures.
"I learned that you have to balance the emotions in a 'winning' situation - when you win and when you lose. So the secret is balance. You can't be too happy when you win in competition and you can't be too sad when you lose the competition because we compete every week. So we have to balance to keep training. And the most important thing is to think about the next competition."
Whatever doubts he had before, that's all part of the past.
"I'm really enjoying [what] I do. And [it's for this] reason that I want to continue fencing, not because I had to, but because I want to."
Zen in training and the Italian tradition
Now Cassarà is making sure that all this mental zen translates to his physical training.
"I can’t train too much because that's too much stress for my body. I have to prepare for some competitions during the season. And I know my body and I have to to prepare and focus not [on all] competitions, but [for] the more important competitions of the season," he said.
He is also changing up his training workouts, incorporating even boxing to keep it exciting and interesting.
"Yes. I see the other fencers like Enzo Lefort and the other French guys do it. Boxing is fun."
But there is nothing like training for a proper competition.
"Training without competition is not easy. And that could be very difficult to restart [in a] competition," he said, "The best training for competition is a competition now. It is good to prepare the body and the mind."
But once competition season restarts with the Coupe du Monde planned for January 2021, Cassarà will be ready to draw upon the very best of Italian fencing to win - the very tradition that has shaped him as the athlete he is today.
"[We] Italians have the right mind for fencing because, you know, it's a situation sport, we are very good at getting by."
Fifth Olympic Games and beyond
Next year, Cassarà and the rest of the Italian squad are planning to give their all and claim a medal haul.
"We wait for five years for the Olympics [Tokyo 2020] so it’s going to be special of course."
"I already won an Olympic Games, I got a gold medal [in the team events in Athens 2004 and London 2012]. So my dream is to get an individual gold medal and [another] team gold medal with my team. I'd like to arrive good and without stress. And I hope to fence in the individual and team competition.
"I think that we have the opportunity to get the medal and the team. And if I arrive in good condition, I can."
He is also looking to face French fencers - who keep a friendly historic rivalry with the Italian team.
"Probably we are going to fence with them in the semi-final at the Olympics. I hope for to arrive in the semifinal. At the beginning of my career, I fancied winning the semi-final with the French."
Not only is he eyeing to compete in Tokyo 2020 but in more Olympic Games.
"For Paris 2024 I would try. Nothing to lose. You know, I'm still enjoying fencing. Next time, we will see the logo of a LA 2028. Joking!," he quipped.
Asked why he remains passionate as he was with the Olympic Games, Cassarà said:
"When you go to the Olympic Games, you understand how small you are. All the world is there - the most popular athletes in the world. And then you understand that it doesn’t just exist for. fencing. But there are [other sports like] swimming, tennis. And if you get the medal, you can feel a very special moment."
When we see Cassarà take the stage next year, we'll see an athlete who has embraced the ups and downs of the sport but who is fully confident to make his mark in Olympic history.
The men's foil individual will be contested on Monday 26 July 2021.