Osceola High’s Bobby Sippio has gone back to his roots this year.
Sippio, who led the OHS Kowboys to their only FHSAA state football championship in the 1998 Class 5A title game before a stellar college career at Western Kentucky, has taken the game of football indoors.
That is, he’s taken it back indoors – as in with the Indoor Football League’s Orlando Pirates.
Sippio, who played briefly in the NFL with the Miami Dolphins, Kansas City Chiefs and Detroit Lions, is a member of the staff of the Orlando indoor team. It was in arenas, as in the Arena Football League, that Sippio, 45, made his biggest splash in pro football.
Earlier this season, Sippio, joined the Pirates as a senior offensive assistant, working with the team’s receivers. That receiving corps includes another local product – Nyqwan Murray played at Orlando’s Oak Ridge High before a college career at Florida State.
“Just trying to stay around the game. I’m trying to share what I know to another generation of guys in this game,” Sippio said. “I know that my name is known around this league.”
Head Coach Ron Windsor, elevated by Pirates ownership from offensive coordinator to head coach after the team parted ways with their prior coach after two games.
“His is a name that brings street cred,” Windsor said. “He’s like a brand ambassador for us, he was here when I came on board. He’s always around helping and been a real positive guy helping the receivers work in our offense.”
Sippio will be on the sidelines Sunday when the Pirates, who were 9-6 in the regular season and, thanks to a 55-54 comeback win over the San Antonion Gunslingers last week, play at the Fishers Events Center with a spot in the IFL playoffs on the line against the Fisher Freight (8-7) at 4 p.m.
Sippio, who was a quarterback at Osceola High and a standout defensive back and return man for Western Kentucky, took the Arena League by storm, first with the Dallas Desperados in 2024-25, making 146 catches for just over 2,000 years and 54 touchdowns; in the 2005 season he scored touchdowns in five different ways during the season, receiving, rushing, interception return, fumble return and kickoff return.
He moved over to the Chicago Rush for the 2006 season, where his connection to Orlando football started – he caught 10 passes for 110 yards and scored three touchdowns for the Rush in ArenaBowl XX against the Orlando Predators in leading Chicago to a 69-61 win.
In 2010 he came home to Orlando to play for the Predators, and in three seasons he tallied 189 receptions for 2,478 yards and 59 touchdowns.
In seven AFL seasons he caught 539 receptions for 7,557 yards and 199 touchdowns.
