Over the past four years, Redwood’s boys’ varsity basketball teams’ sudden rise to dominance in the Marin County Athletic League (MCAL) and beyond has thrilled the hardworking players and fired up the fans who fill the stands. One key individual has spurred the success and potential victorious future for the Giants; Jay DeMaestri, the varsity boys’ basketball coach and popular dreadlocked figure at Redwood High School.

Fresh off of his fourth season and seventh year here at Redwood, DeMaestri has led the team to three MCAL finals in the last three years and won two. Additional banners hung in the gym will forever commemorate his success.

DeMaestri attended Tamalpais High School and has been playing basketball since he could walk. Brandon Johnson, a former Redwood High School campus

assistant and DeMaestri’s best friend, explains his experience watching DeMaestri play while growing up.

 “I looked up to him in high school when he was a player. He was a phenomenal athlete at Tam, MCAL first-team all-Leaguer, and I’m sure he got some MVP votes as well,”  Johnson said.

Continuing his career, DeMaestri committed to play Division II basketball at Cal State Monterey for two years. After college, DeMaestri moved to East Germany to play professional basketball. 

“I didn’t really like it and I didn’t fit [in]. They traded me out to Western Germany. I fit in a lot better over there, as the culture was more westernized and there was a lot more English,” DeMaestri said.

After his professional overseas career concluded, DeMaestri returned to Marin County. “I had no real plan, but I knew basketball,” DeMaestri said.

He discovered the North Bay Basketball Academy [NBBA] basketball club. He fell in love with coaching kids and knew that he wanted to continue to do so. He coached for other Marin high schools, but his dream job was always to be the Redwood boys’ varsity basketball coach. 

Since becoming the coach, DeMaestri has built strong connections with the team’s players. Brady Weingart is a current senior on the varsity boy’s basketball team and has been coached and mentored by DeMaestri for seven years. 

“[DeMaestri] is very hard on you when he needs to be. He demands his respect, but at the same time, he treats you like a player on the court and outside the court. He treats you like a friend, so you build a bond with him and respect him all at the same time,” Weingart said.

Being a campus assistant comes with many parts, including relationships on and off the court. One of DeMaestri’s favorite things about working at Redwood is the time he spends with students, which provides DeMaestri with a lot of experience with balancing relationships and respect. 

“I always say, we can joke around and have fun outside of the gym. But when we step into the gym, that’s when I become ‘coach’. We really just all play for each other,” DeMaestri said. 

Being a role model is not simple and takes a lot of work. DeMaestri has mastered that and knows the skills it takes to be one. 

“It’s not about screaming, yelling and being as loud as you can. It takes a different approach. Kids here, they’re so smart. They pick up on anything and see through the fakeness and if you ever have any, they’ll just call you out for it,” DeMaestri said.

One of the highlights of DeMaestri’s career was leading the team to a championship last year, along with junior varsity coach, Brandon Johnson.

“The best memory working with [DeMaestri] was watching him win the MCAL finals in 2022. Watching him as a coach and setting a goal for the program was really inspiring to see. He’s super hard-working, and he cares about the kids a lot. He puts his heart into it,” Johnson said.

DeMaestri looks forward to continuing his career as the Redwood boys’ varsity basketball coach and believes he will bring home more banners with the boys.