Skyline against Mesquite

Skyline head coach Brian Gregory in the dugout against Mesquite, Monday, March 7, 2022, in Gilbert, Arizona. (David Minton/Staff Photographer)

The clouds were heavy and clustered over the varsity baseball field at Skyline High School. It would’ve been opening day for the Coyotes had the rain stayed away.

Instead, Brian Gregory, Skyline's head coach, found himself in the school’s weight room recounting what had led to him being hired by Skyline earlier this school year.

Gregory was a player for a long time. He started playing baseball when he was 4 or 5, playing in the local little league of Lompoc, Calif. where he was born and raised. At around 7 or 8 years old, Gregory started catching.

He was a young high schooler by all accounts. He entered high school as a 13-year-old and was invited to start playing in Cabrillo High School’s summer baseball program by Jon Osborne, the head coach at Cabrillo. Many of the kids he played with were 18.

“Looking back on it the guy must’ve only been throwing the ball 82 or 83 miles an hour but I remember as a 13-year-old you’re like ‘Oh my gosh, this is hard. But it’s something that I want to do.’ And I loved the challenge of it,” said Gregory.

He knew he wanted to play college baseball after having four highly successful high school seasons and was able to get opportunities to do so in California.

Gregory went to Allan Hancock College as a 17-year-old. He played baseball there throughout the summer until the day of his birthday.

“I’ll never forget. On my birthday, in the rain, we had our first cuts of the fall. We had to go look at a classroom list,” Gregory said. “I looked and my name was on the list. I couldn’t believe it. It’s not like someone saying ‘Hey, you’re not good enough’. It was just a list posted, in the rain, on my birthday. Cut.”

He found his way to Santa Barbara City College for the remainder of the fall semester.

He then had back surgery at 19 and was sidelined. He finished his seasons at Santa Barbara and started a handful of games behind the plate.

Gregory earned a preferred walk-on opportunity to Cal State Dominguez Hills. If Gregory got into the school on academic grounds, he would be a part of the team workouts and get an opportunity to be on the team.

He ended up injured and redshirted his first year. He had a solid junior season and earned the starting catching job as a senior. It was an up and down season but by the last five games he had turned it around. Unfortunately, it was also the end of his college career.

Ultimately, Gregory decided to try out for Independent League teams and played for a few more years. He played for the Raton Osos in Raton, New Mexico and bounced around until his last season in 2015 when he was playing for Kelly Stinette, an ex-Diamondback and manager of the Watertown Bucks at the time. 

After Gregory’s year was cut short when he broke his finger while catching in the bullpen, he began to consider a path to coaching.

He always knew to an extent that he was meant to coach even from a young age. Gregory’s grandfather is part of the reason that he is coaching now. Looking back on fond memories of his grandfather, Gregory started to tear up.

“He supported me all throughout high school,” Gregory said. “When I started to get into coaching, he was pretty influential as far as that goes and supported me on that. Obviously, I get emotional about it because he is such an influential person in my life.”

Gregory got his first real taste of coaching when went back home to California with his old high school team.

His former coach, Jon Osborne, loved having him back with the team because he was a good role model for the players.

“When he came back, it was nice to have former players that were playing past high school to come back and work out with the team,” Osborne said. “He was really good working with the players and had a really good rapport as a student athlete. He was a good role model because he always worked really, really hard.”

Gregory eventually found himself searching for a high school coaching job in Arizona after he and his wife, Matiana, relocated. He became an assistant coach at Dobson under then head coach Phil Wail.

Wail, now the athletic director at Skyline, brought him on to coach the Coyotes when former coach Pat Herrera stepped down.

He began working with the kids to build a team that could get to and win playoff games this season and also give them the experience and skills he learned in high school.

The oldest of six children, Gregory learned how to mediate debates, how to be responsible for others and how to be accountable.

Gregory said that part of the reason he wanted to work so hard at baseball is because he knew that younger siblings always looked up to him. They looked to him to see what work ethic, commitment and responsibility were.

He’s now getting a chance to share all he learned with the Skyline players.

“You want to win games and be the best,” Gregory said. “At the same time, you’re preparing these kids for life after baseball. You don’t know what type of impact you will have on these kids and even if it’s not on the baseball field you want to see these kids be successful.”

Have an interesting story? Contact Zach Alvira at (480)898-5630 or Follow him on Twitter @ZachAlvira


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