It's fair to say Wolf, 39, a Francis Parker School graduate and West Rogers Park resident, has been facing an uphill battle to succeed in judo ever since he lost those first 14 bouts as a 5-year-old.
For the most part since then, Wolf has devoted his life to the sport, building a successful business teaching it to youngsters throughout Chicago and coaching in several national and international competitions.
"Brett is kind of like the Pied Piper of kids," said his younger sister, Hillary Wolf, a two-time Olympian in judo and the first American woman to win a Junior World Championship gold medal. "They love him. He has a great rapport with kids. He believes in them regardless of their skill level, and he gets the most out of them."
Wolf, a fifth-degree black belt, said leading Team USA at the Junior (Under 21) World Championships in Ljubljana, Slovenia, later this month is his "Super Bowl."
"This is a big deal for me," said Wolf, who is co-head coaching with Jhonny Prado of Ki-Itsu-Sai in Coconut Creek, Fla. "I worked as hard as I could to make this a reality. It doesn't get any bigger than this for junior judo, and I'm glad USA Judo has the trust in me to take the best players in the country to the top junior tournament in the world. That's something I take very seriously."
From humble beginnings
Wolf's father, Malcolm, said the 0-14 beginning never deterred his son.
"All of a sudden, he started winning and he found out he was pretty good at it," said Malcolm Wolf, a Hyde Park native who lives in Lincoln Park.
Brett's one down period in the sport was when he quit in high school to focus on tennis and basketball, where he was Parker's co-captain. His dad said he could have been better but didn't want to put the time into training.
That wasn't the case for Hillary, who gave up a career in movies, which included roles in the "Home Alone" series, to focus on judo. All the while, Brett was her biggest cheerleader.
"He easily could have been mad at the attention I was getting, but he really was always supportive," said Hillary, who retired after the 2000 Olympics and lives in Colorado Springs, Colo.
The acclaim Hillary earned in competitions, Brett has achieved in coaching, which began before he turned 20.
After high school graduation, Wolf was asked by Menomonee's head sensei Tony Dangerfield to return to the club to instruct youngsters.
"I got on the mat, and you know what, I just knew that's what I wanted to do with my life," Wolf said.
Making Menomonee a player in American judo
There are only 30,000 judo players in the United States. There are more than 1 million in France alone.
But Wolf was determined to build Menomonee, based at the Drucker Center in Lincoln Park, into one of the U.S.'s top judo clubs, especially after taking over as lead sensei in 1998.
Menomonee has flourished, with 300 youth players in various programs across Chicago. Wolf teaches 25 classes over five or six days per week.
Wolf also has created the country's largest Paralympic judo club for visually impaired players, with Menomonee being named the Paralympic National Training Site by USA Judo last year. And Wolf has his eye on the head coaching gig for the 2016 Paralympics in Rio de Janeiro.
"He found a niche for himself that I guess is just perfect for him," Hillary Wolf said. "He’s taken it to such a higher level with all the kids he has in his program and the diversity of his program. It’s lucrative, he loves the kids, the parents love him, and it works in all aspects."
Internationally, Wolf has built his reputation while serving as an assistant coach at the 2011 Junior World Championships in Cape Town and a member of the Junior Pan American coaching staff for the last three years.
"He genuinely cares about us," said George Truong, 18, one of Team USA's medal hopefuls at the Junior Worlds, who lives with his sister and fellow Team USA member Summer Truong in Colorado Springs. "Even though he lives in Chicago, he's always texting us to see how we're doing. His biggest strength as a coach is being able to get the athletes' trust and earn their trust."
Wolf's squad is not favored to win a medal in Slovenia. An American boy hasn't been on the medal stand since 1992, and Hillary Wolf is one of only three U.S. girls to ever wear a gold medal.
Still, Wolf has confidence.
"We have some experienced players, and we're not going to be a joke," he said.
Wolf said he's going to stick with judo as long as his body will hold up. Even at 39, it's getting tougher by the day to pick up mats and move them around. He said he's been lucky to stay injury free.
And looking back to his inauspicious start, Wolf can't believe his good fortune.
"All of the struggles, all of the sacrifices, it's been worth it and really fantastic," he said.