Circuit Judge Kenneth Lester referred to Zimmerman with words like "conceal" and "flee" more than a dozen times in an eight-page order that would let him out of jail while he awaits his second-degree murder trial in the shooting of unarmed teenager Trayvon Martin.
The judge's doubts could hurt an attempt by Zimmerman to dismiss the case by claiming he shot Martin in self-defense, a possible motion based on Florida's "stand your ground" law, experts said.
"Mr. Zimmerman is not held in any high esteem by this court," said Karin Moore, a law professor at the Florida A&M University College of Law. "I think that could matter if there is a `stand your ground' hearing ... It's a matter of credibility. There is no one else to testify to support the self-defense claim."
Lester had revoked Zimmerman's $150,000 bond last month after prosecutors said Zimmerman and his wife misled the court about how much money they had during an April bond hearing and failed to disclose he had a second passport after turning in one passport to the court.
"Under any definition, the defendant has flaunted the system," Lester said. "Although there is no record of flight to avoid prosecution, this court finds that circumstances indicate that the defendant was preparing to flee to avoid prosecution but such plans were thwarted."
The judge set much stricter bail terms than those established during Zimmerman's April hearing, addressing concerns that he would flee. The 28-year-old must stay in Seminole County -- he was allowed to leave Florida after his first release. He must be electronically monitored, can't open a bank account, obtain a passport or set foot on the grounds of the local airport. He has a 6 p.m. to 6 a.m. curfew.
"Judge Lester didn't like being lied to," said Orlando attorney Blaine McChesney, who has been following the case. "It is apparent from the opinion that, had Judge Lester, felt he had more discretion under the current law, he would have denied a bond."
Zimmerman, who formerly lived in Sanford, had not yet been released from jail and his arrangements after his release were unclear.
Zimmerman will have to pay a bail bond company $100,000 and have collateral worth $1 million. Neither Zimmerman nor his family have that amount in collateral, O'Mara said on his website in an appeal to supporters to donate. The fund now has $211,000 in it, O'Mara said.
"For those who have given in the past, for those who have thought about giving ... now is the time to show your support," O'Mara said.
The vitriol that was directed at Zimmerman after Martin's death during a Feb. 26 confrontation in a Seminole County gated community has died down, but the intense media scrutiny of the case also will keep the spotlight on Zimmerman once he is released, with local media following him everywhere he goes.
The 44 days between the shooting and Zimmerman's arrest inspired nationwide protests, led to the departure of the Sanford, Fla. police chief and prompted a U.S. Justice Department probe.
Martin's parents and supporters claim that the unarmed teenager was targeted because he was black and that Zimmerman started the confrontation that led to the shooting. Zimmerman's father is white and his mother is Hispanic.
Prosecutors said a website Zimmerman created for his legal defense had raised $135,000 at the time of his first bond hearing. Zimmerman and his wife did not mention the money then, and Shellie Zimmerman even said the couple had limited resources because she was a student and he wasn't working.
Prosecutors argued Zimmerman and his wife talked in code during recorded jailhouse conversations about how to transfer the donations to different bank accounts. For example, George Zimmerman at one point asked how much money they had. She replied "$155." Prosecutors allege that was code for $155,000. Their reference to "Peter Pan" was code for the PayPal system through which the donations were made, prosecutors said.
Shellie Zimmerman faces arraignment at the end of the month on a perjury charge; she was freed on bond.
During a second bond hearing last week, O'Mara sparred with prosecutors over those finances and questioned why his client is in jail at all, arguing that Martin's actions led to his death. O'Mara said that his client was confused, fearful and experienced a moment of weakness when he and his wife misled the court.
The judge didn't buy it and chided Zimmerman for even misleading his attorney. O'Mara has said he didn't know how much money had been raised by the website at the time of the April hearing.
"The defendant has tried to manipulate the system when he has been presented the opportunity to do so," Lester said.
Zimmerman has pleaded not guilty to second-degree murder and claims the shooting was self-defense under the state's "stand your ground" law.
The law allows individuals to use deadly force provided they are doing nothing illegal and relieves them of a duty to retreat if they believe their lives are in jeopardy. The law allows defendants to make their self-defense case at a hearing presided over by a judge and without the use of a jury. If the judge deems self-defense was justified, the case can be dismissed without going to trial.