He pleaded guilty earlier this year as part of a plea agreement.
Federal agents seized his iPhones. They also seized his laptop computer. In numerous message threads dating back years, Napolitano discussed his interest in enticing and having sex with "young" (slang for minors), according to court records.
Authorities said he met a 15-year-old boy on Grindr and had a sexual relationship with him for years.
Napolitano knew the victim was a minor and a student at a local school, according to court records.
Napolitano worked for Pasco County Schools as a Transportation Manager. He was in charge of buses that take thousands of kids to and from school.
Napolitano's defense attorney, John Trevena, said his client is remorseful.
"This gentleman had engaged in substantial cooperation with the federal government. He pleaded guilty early in the case. So what is his reward? To get the maximum?" said John Trevena.
Cameras are not allowed in federal court.
At the sentencing hearing, the victim's family member spoke saying the words "child predator" should be across Napolitano's forehead.
She explained how Napolitano came to her house and molested a child under her care.
Napolitano showed no emotion in court until his mother spoke to the judge.
She said she loves her son and she said she failed him.
"The mother is heartbroken. She is up there crying hysterically, inconsolable. The co-worker is crying," said Trevena.
Napolitano spoke in court and asked a judge for a "second chance." He said he was sorry.
A judge said she must protect the public and protect children who are too vulnerable. She said the only appropriate sentence was life in prison.