Lely QB Recalls School's Last Coconut Bowl Victory

When the O’Regan family looks at the photograph of Sean O'Regan holding the Coconut Bowl trophy over his head, surrounded by his teammates, it brings back happy memories. O’Regan had just thrown a touchdown pass in overtime to defeat Naples, 12-6, in the Coconut Bowl 37 in 2009. It’s the last time the Trojans have won the famous game, which is the third-longest continuous high school football rivalry in the state.

"That's been a coveted photo in my family for a while now,” O’Regan said. “The big thing I remember is after throwing the winning touchdown pass, it didn't really hit me that we won until I saw my dad come running at me. He lifted me up, and that's when it all hit me. He coached me through all the way up until high school. And after I threw a touchdown pass in Pop Warner, I'd run to my dad on the sideline and he'd lift me up. So, it was a pretty cool moment.”

Michael “Moose" and Mary Jo O’Regan covet the photo of their son that’s on display in their Marco Island restaurant, Paddy Murphy’s. You can hear the excitement in Moose’s voice as he recalls his son’s Coconut Bowl moment at Naples High School’s Staver Field.

“I ran down and started climbing over the fence to get onto the field,” Moose said. “A cop saw me and told me to stop. I said, ‘But that’s my son who just threw the touchdown pass!’ He looked and me and said, ‘Oh, go ahead.’” Moments later the Lely bleachers emptied onto the field.

"I think he was the first one on the field,” Sean said. "A lot of people stormed the field. He likes to tell that story. He was the first one over that fence.”

Sean said by all rights the Trojans should have won the game in regulation.

"It shouldn't have went to overtime,” he said. "I threw two touchdown passes in a row that got called back due to penalties. I think we were on the five or 10-yard line. I think both of them were to Michael Snyder. Two in a row. Then we went to overtime and I threw a 10-yard fade pass to Romanthi Mathurin to win it.”

O’Regan almost didn’t have the opportunity to be the hero of Coconut Bowl 37.

"Coach Dave Miller, he was the interim head coach at the time, had a conversation with me at halftime. I didn't have the greatest first half, and he was considering benching me. I told him, ‘No, coach, I've got this.' I went out and I had a great second half. We ended up winning. He wasn't on the field. He was up in the booth calling plays. He came down and hugged me and said, ‘You said you'd do it. You did it!' So, I always remember that. That was pretty cool. I'm glad he believed in me and kept me in.”

Sean O’Regan recently moved back to the area after living in Wisconsin. He said there will be a strong showing from his family at this year’s Coconut Bowl at Trojan Stadium on Friday, October 17, at 7:30.

“It looks like my dad's going to be there,” he said. "My brother will be there. We just had our high school reunion. We didn't have our 10-year reunion because of Covid. So, we had our 15-year reunion just a few months ago. So, everyone reconnected just recently and everyone's been talking about, ‘Hey, are you guys planning on going?' So, it seems like there will be a big crowd, as it looks like this is one of Lely's best chances to win. I've been seeing the scores, and they've been running up the score on a lot of people, so the chances look good that it will be a win on Friday.”

Sean will be there with his wife and young son.

"My wife was the captain of the cheerleading team at the time,” he said. ’So maybe she can cheer the team to victory again. She's Cristina Martinez, of course, now she's Cristina O'Regan. She was the homecoming queen, too. I haven't been to a game since I graduated. I lived in Wisconsin for some time. I played football in college up there at a small Division III school, Saint Norbert College, which is right next to Green Bay. I haven't been to a game because I have two young children and the games are pretty late for them. But my son is really getting into football. He's five years old, and I coach his flag football team now on Marco. He's getting really into watching football on TV, and this will be his first experience watching a live football game at any level. So, it will be fun to have his first experience be the Coconut Bowl. Maybe we'll be the good luck charm.”