Raymond returns: Longtime MIA basketball coach back in SWFL this weekend

Head coach Roger Raymond embraces team captain Cole Stretton at the end of Friday’s easy 85-72 win over Oasis Charter.

When Roger Raymond and his family left Marco Island last year after 35 years, he knew he’d miss all the friends left behind.

That’s why he’s hoping to see some of them this week when he returns to Southwest Florida. The former athletic director and boys basketball coach at Marco Island Academy now serves as the assistant girls basketball coach and head cross country coach at Kissimmee-Osceola High School. His new team will play in a Fort Myers tournament this weekend.

Osceola will play Lehigh at 6 p.m. Friday. The Kowboys then take on two-time defending state champion Fort Myers at 2 p.m. Saturday.

“I’m hoping a few Marco people show up so we can catch up a little bit,” Raymond said. “I’ll be putting it out there on Facebook that I’ll be (in Fort Myers). It will be nice to see my friends again.”

Prep basketball: Roger Raymond steps down as Marco Island Academy boys coach

Raymond left Marco Island last summer due to a family medical emergency with his daughter. She’s doing much better now, and he and wife Karen are finally beginning to acclimate themselves to their new surroundings.

“Having been on Marco for 35 years, we just don’t have the connections here that we had down there,” he said. “You go down the street and you always run into someone you know. Go for a run, same thing. That’s been the biggest adjustment, that complete loss of a connection to your community.”

As always, Raymond is enjoying coaching and helping make an impact in young athletes’ lives. Osceola’s head basketball coach Sarah Dileonardo is a relative newcomer to coaching, taking over the reins of the program last year after playing college basketball at Division II Webber International University. Raymond, 66, says the relationship is paying off dividends. After going 11-14 last year in their first year together, the Kowboys are off to a 5-0 start this season.

“She knows I’ve been around the block, so I try to help her anyway I can,” he said. “She’s really good with the kids and an assistant coach; she never shuts me out. I can say anything I want and she’ll take what I say into consideration. You don’t always have that kind of relationship with a head coach when you’re the assistant.”

He says his work as the head cross country coach has been a bit more challenging.

“It’s definitely a work in progress,” he said. “The demographics are a bit different. Up here, everybody seems to be fast but we’ve got no distance runners. We’re trying to change that and hopefully develop some distance runners.”

Raymond wouldn’t rule out an eventual return to Marco Island, although he says it’s something he hasn’t thought about much.

“So many things could happen,” he said. “But whether we ever move back or not, Marco will always be our home.”