Jay DeMaestri is a journeyman.

While the students of Redwood may not see a story behind the dreadlocks and sunglasses of their newest campus supervisor, DeMaestri’s story is far from simple. 

“Sports have always been a huge part of my life,” DeMaestri said.

His journey began with his years on Tamalpais High School’s varsity basketball team, which eventually inspired the path he would later follow.

His journey started at Tam and later continued to Cal State Monterey and the University of Hawaii, Hilo. DeMaestri would take his basketball skills all the way to the professional level, eventually playing in Germany. 

So how did he end up at Redwood? For DeMaestri, his journeys brought him back to the place where it all began.

DeMaestri’s legacy in Marin County began before he was even born.

“My grandfather also went to Tam back in the day,” DeMaestri said. “He played baseball and actually went on to play in the majors.”

That was why before even setting foot on his high school campus, where a jersey with his name on it hung above the baseball field, DeMaestri had lofty expectations for himself, both on and off the field.

“I was never a straight-A student,” DeMaestri said. “I made myself do well in school because I realized that if my grades slipped I couldn’t play basketball.”

While his jersey would not hang in the rafters like his grandfather’s did, DeMaestri carried his basketball career beyond the confines of high school.

After graduating Tam, he moved on to Cal State Monterey Bay, where he played basketball on a scholarship for two years before transferring to the University of Hawaii, Hilo, to play basketball and earn his major in communications.

After college, he set off to play professionally in Europe. DeMaestri played in Cottbus, Germany for the Cottbus White Devils as well as in Paderborn for the Paderborn Baskets.

“Cottbus was in East Germany. I didn’t really enjoy myself there. Once I got traded to West Germany,  was much more comfortable,” DeMaestri said.

DeMaestri said that Paderborn was much more westernized, making it an easier place to live.

After his basketball career in Germany ended, DeMaestri headed back home to Marin.

“I didn’t really know what I wanted to do with myself,” DeMaestri said. “I never thought that I would ever work with kids.”

Though unsure of what he wanted to pursuit back in Marin, his love for basketball drew him into working as a coach at the North Bay Basketball Association, where he has worked for five years.

“For me, [working with kids] was pretty addicting. It keeps you guessing,” DeMaestri said. “It’s not the same thing over and over like if you were working in an office. It keeps me on my toes.”

Coaching soon became his career. Previously, he coached a freshman basketball team in San Rafael, but now coaches the Junior Varsity team at Tam.

DeMaestri’s main reason for coming to Redwood was the “team aspect” of the job. Having been a part of a team his whole life, working as campus supervisor felt like second nature.

“I like trying to get through to certain kids and just help them out,” DeMaestri said.

Because of DeMaestri’s prior experience at  Tam, he felt that he knew what to expect and felt he knew what many kids are going through.

For someone who has been across the world, DeMaestri says his motivation has always been competition.

“People need competition, whether it be in your job, your sport, or amongst your friends,” DeMaestri said. “Competition is what drives people to be great.”