Winter Park High School names Sid Cash Jr. as its new varsity baseball head coach | Observer Preps

After two-and-a-half months of searching for someone to take the helm of the baseball program, in the end, Winter Park didn’t have far to look.

Among all the candidates, three stood out among the group thanks to their familiarity with the community, but there was one who just caught the attention of Athletic Director Michael Brown.

The man they had been looking for was Sid Cash Jr., and he was right there all along — serving as a third-year assistant coach on the Winter Park junior varsity squad.

But now, the Winter Park native has a new title — that of varsity head baseball coach.

“I’m very excited about it — it’s a fantastic opportunity,” Cash said. “I was born and raised in the community and have lived here all 49 years of my life. It’s an honor to be associated with Winter Park High School and an honor for them to trust me with this program.”

Cash is just the third in 38 years to serve in the role as head coach for the Wildcats. A majority of that time — 32 years — legendary coach Bob King led the program to prosperity before retiring in 2015.

Following King’s retirement, former UCF baseball and football standout Dee Brown took over. Despite decent success — including a district and conference title in 2016 — Brown and two assistants were fired after being suspended for “abusive profanity” following the Wildcats’ district semifinal loss against Timber Creek in May.

“I was born and raised in the community and have lived here all 49 years of my life. It’s an honor to be associated with Winter Park High School and an honor for them to trust me with this program.”

- Sid Cash Jr.

But despite the tough end to last season, Cash is ready to lead the Wildcats into the future.

Although he graduated from Lake Highland Prep in 1987, Cash is purely a Winter Parker. He played Little League ball locally, and attended Dommerich Elementary and Maitland Middle School, before making his way to Winter Park High for a bit before transferring to LHP.

Although Cash continued his playing at Florida State University, coaching emerged as his true passion. His father is Sid Cash — a Winter Park alum who helped lead a group of Maitland 12-year-olds to the Little League World Series in 2005.

“The coaching bug I probably got from my father,” Cash said. “To be able to coach at his high-school alma mater 50-something years later is pretty cool for me to be able to say.”

Not only will Cash be representing the alma mater of his father, but he will also represent his four children — one of whom has graduated, two of whom are current students and the last who will be attending the school in the future. He’ll also have the chance to teach and spend time with his son, Gaines, a senior on the baseball team.

“It’s a great opportunity to be able to coach my son; we spend a lot of time together on the baseball field,” Cash said. “When this opportunity came about, I knew my son’s opinion of it would be favorable, but I had to meet with my wife and three daughters, because I want to be involved with them … and they were all very supportive and gung-ho about it.”

Many years of learning under his dad has helped Cash prepare for the upcoming task he has at Winter Park.

“Coaching is my passion — I love seeing kids get better, I love seeing kids improve, and I love when they have a chance to succeed,” Cash said. “Baseball is really the only game that is a game of failure — you’re going to fail more than you succeed — I think it teaches us so much about life.”