Trayvon Martin case’s mystery man: George Zimmerman’s cop connection

Lingering suspicions perked up again this week after prosecutors released evidence that showed an email connection between Zimmerman and now-fired Sanford Police Chief Bill Lee, where the two exchanged amicable notes about the resolution of a case where a previous chief refused to charge the son of a police lieutenant for the beating of a homeless black man.

Moreover, Mr. Lee, who spent 30 years at the Seminole County Sheriff’s Department, may have known Osterman since their tenures at the department overlapped. At any one time, the Seminole County Sheriff’s Department has more than 500 employees.

Osterman was fired from the sheriff’s office in 1998 in the midst of a scandal where he and a fellow officer were duped into off-duty security gigs by a con man claiming to be a famous baseball star named Juan Diaz. Osterman took the job without getting permission from the sheriff, which compounded the embarrassment and led to his firing.

Osterman has since worked as a beach guard and since the early 2000s as a federal air marshal, which were hired in large numbers after 9/11 to provide covert security on flights.

In his April interview with the FBI, Osterman claimed Zimmerman was estranged from his parents until the shooting, and that he had feared the New Black Panther Party, which put a $10,000 bounty on Zimmerman after the shooting.

“Zimmerman is very concerned with all the negative reaction from the press and others and wants more evidence released to show what really happened,” Osterman told the FBI.

But Osterman denied having any influence on Zimmerman other than as a friend and confidante, according to documents obtained by the Herald. During his conversations with Zimmerman, Zimmerman “never asked … what not to say during his interviews with the police,” according to the FBI. Osterman “stated Zimmerman did not understand the process and his only advice to Zimmerman was to tell the truth.”

Zimmerman, on at least one occasion, did not heed that advice. He was remanded back to jail by Judge Kenneth Lester in June after it was revealed he had conspired with his wife, Shellie, to keep $135,000 worth of donations out of the court’s eye, in order to win a low bond. Shellie was charged, booked and released on a perjury charge after the initial bond was revoked.

Most recently, the judge’s suggestion at a recent bond ruling that Zimmerman had “flaunted the system” and engineered “deception upon the court” became Zimmerman’s basis for a motion to remove Judge Lester, filed Friday. The motion chided Lester for “words crafting an order that was harsh and morally indignant” while failing to address the self-defense claims.

While Zimmerman’s lawyer Mark O’Mara explained at that hearing that Zimmerman was young, confused, and distrustful of a system that seemed to be discounting clear evidence of self-defense, Judge Lester articulated another view of Zimmerman: as a knowing manipulator who – based on lies about the money and a second passport Zimmerman had procured – was planning to flee the country to avoid a trial.

After rapping Zimmerman for his behavior, Lester released him on a $1 million bond earlier this month. Zimmerman is currently in hiding somewhere in Seminole County. 

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