The record shows Osterman also accompanied Zimmerman for a video walk-through of the shooting scene with police, and went to his third interview with Sanford Det. Chris Serino. In a police surveillance camera video shot three days after the killing, Osterman can be seen standing in the police lobby and going up the stairs.
“During his conversations with Zimmerman, Zimmerman never asked… what not to say during his interviews with the police,” the interview summary said. Osterman “stated Zimmerman did not understand the process and his only advice to Zimmerman was to tell the truth.”
In his FBI statement, Serino said Zimmerman sounded “scripted.”
From the start, lawyers representing Trayvon’s family questioned whether Zimmerman had help from some outside law enforcement influence. Some suspected it was his dad, a retired Virginia magistrate. Others accused Seminole State Attorney Norm Wolfinger of pulling strings to keep him out of jail.
Trayvon’s family lawyer, Natalie Jackson, raised the question Thursday whether Osterman was friends with former Sanford police chief Bill Lee, who spent 30 years at the Seminole County Sheriff’s department and trained many deputies at the academy.
Osterman was a Seminole County Sheriff’s Deputy assigned to patrol and a school resource officer for six years.
He lost that job in 1998, when he and another colleague were fooled by con man Juan Diaz, who told the two cops that he was a second baseman for the New York Yankees and needed bodyguards. Diaz drove an expensive sports car, went to strip clubs and flashed money around — with the two officers in tow, according to 1998 news reports.
But Diaz was later revealed to be a fraud, and was arrested for writing a phony check for a $38,000 Ford Expedition he bought, the Orlando Sentinel reported at the time. Because the two officers never got permission to work an off-duty security detail, the sheriff fired them. “The guy was very wealthy. He had a hundred-thousand-dollar sports car. I had no reason not to believe that he wasn’t who he said he was,” the Orlando Sentinel quoted Osterman as saying at the time, from transcripts of his hearing. “I started to realize that this guy wasn’t all that he said he was. I started going to baseball card shops.... I really know nothing about baseball. I’m not a big baseball fan, but no one knew who a Juan Diaz was.’’
Osterman grew suspicious when he caught Diaz in little lies and when Diaz often didn’t have money to pick up tabs.
“He lied about everything,’’ Osterman said at the hearing.
According to the Sentinel, the officers figured out the check for the Ford was worthless but instead of reporting the car stolen, they hit the dealer up for a friend to get a finder’s fee for the vehicle’s return.
The newspaper reported that they appealed their dismissal and eventually resigned.
An online police database shows the former Army veteran later went to the Volusia County Beach Patrol. Osterman’s Facebook profile says he has worked for the Department of Homeland Security since 2001. On Facebook, Osterman describes his job as “lots of shooting and traveling.” Air marshals travel incognito, ready to act when flights are hijacked.