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With the trial of neighborhood watchman George Zimmerman pending in the killing of Trayvon Martin, information released by the prosecution is creating questions about Mr. Zimmerman鈥檚 character and credibility, which legal experts say could be damaging in the courtroom.

Zimmerman is pleading not guilty to second-degree murder charges in the killing of Mr. Martin, a Florida teenager. The case has attracted international attention both for possible racial motives in the case and questions about Zimmerman, who remains an elusive and, according to the presiding judge, deceptive figure.

Tapes made public Monday by prosecutors involved material whose admissibility as evidence is far from assured, including allegations that for years, as a minor, he sexually groped a girl two years his junior whom he saw at family gatherings, as well as evidence that he lied to the judge about his family鈥檚 finances.

Zimmerman鈥檚 attorneys tried and failed to block the release of the tapes.

The tapes suggest Zimmerman knew of fundraising efforts on his behalf before a bond hearing in April at which his wife testified that the couple was destitute in an effort to get a reduced bond. A $150,000 bond was granted.

After prosecutors revealed that Zimmerman鈥檚 family had transferred about $135,000 in online donations into their personal bank account five days prior to the hearing, Seminole County Circuit Judge Kenneth Lester sent Zimmerman back to jail and last week charged Shellie Zimmerman, his wife, with perjury.

Judge Lester also noted Zimmerman failed to disclose a second passport held in a safe deposit box and suggested he was a possible flight risk.

A jailhouse tape, one of 150 released Monday, suggest Zimmerman and his defense attorney knew of the donations before the initial bond hearing. In an April 14 phone conversation between Zimmerman and a family friend, Zimmerman is heard saying he told his defense attorney of his attempt to transfer $37,000 from his online legal defense fund site into an online banking account, but was blocked because the amount was too high.

Zimmerman told the friend his attorney was going to have him 鈥渄eclared indigent.鈥� 鈥淚 told him I didn鈥檛 think that would be possible [in light of the attempted transfer].鈥� He said: 鈥榃ell, that doesn鈥檛 matter. Right now you鈥檙e not working. You鈥檙e not providing an income for your family. You鈥檙e probably not going to be employable for the rest of your life.鈥� 鈥�

Defense Attorney Mark O鈥橫ara told the Miami Herald Monday he was not aware of the conversation. 鈥淚t鈥檚 not the type of thing you would risk your license to practice law over,鈥� he said.

In a second bond hearing, Lester set a $1 million bail for Zimmerman. Mr. O鈥橫ara filed a motion Friday to remove Judge Lester from the case, claiming bias against Zimmerman based on statements Lester made in his order to set bail that accused Zimmerman of 鈥渄eception鈥� and flouting 鈥渢he system.鈥� O鈥橫ara鈥檚 motion described the remarks as 鈥済ratuitous, disparaging.鈥� 鈥淏ecause of this prejudice, [Zimmerman] cannot receive a fair and impartial trial or hearing by this Court,鈥� the motion reads.

In April, O鈥橫ara successfully removed the first judge handling the Zimmerman case after they revealed her husband works for a law firm that provides legal analysis for CNN and had been considered as a prospective defense attorney in the case.

The legal wrangling in the case to date will present difficulties for Zimmerman in the eventual trial to maintain credibility to jurors, legal experts say.

鈥淭here are potential enormous negative ramifications presented as a result of this entire bail debacle,鈥� says Marcellus McRae, a former US prosecutor now in private practice in Los Angeles. 鈥淵ou already have someone the judge has signaled in this context has credibility problems. You have to think you don鈥檛 get that many missteps before it becomes even more critical.鈥�

Zimmerman did not testify in the bail hearing, which Mr. McRae says suggest his attorneys are planning to keep him off the stand during a trial. That decision, McRae says, 鈥渨ill significantly undermine his effort to get his story across,鈥� which might otherwise be considered powerful testimony when compared to prosecutorial witnesses who were not present at the time of the killing.

Another complication for Zimmerman is his wife, Shellie Zimmerman, who is now embroiled in criminal charges of her own. That makes her credibility suffer, which is a loss considering spouses of criminal defendants are often powerful advocates in the courtroom.

鈥淵ou鈥檝e got a situation where perhaps two of the chief advocates for Mr. Zimmerman may be silenced. Or, if they aren鈥檛 silenced, significantly undermine his credibility,鈥� McRae says.

Another tape released Monday is of an unnamed woman, identified by the defense as a cousin of Zimmerman's, who is heard telling investigators he sexually groped her when they were young children. The woman said Zimmerman first molested her when she was 6 and the episodes continued until she was around 16. Zimmerman is two years older than the accuser.

Her family confronted Zimmerman years later but they failed to file criminal charges, she said.

Although it is not yet known how prosecutors plan to use the woman鈥檚 accusations, Jules Epstein, a law professor at Widener University of Law in Philadelphia who specializes in cases involving sex crimes, finds it 鈥渦nimaginable鈥� the statements would be admissible in the trial.

The tape 鈥渄oesn鈥檛 provide context, it doesn鈥檛 explain motive, it doesn鈥檛 do anything鈥� related to the Martin killing, Mr. Epstein says. Another difficulty with the admission is that the incidents allegedly took place so far in the past.

O鈥橫ara鈥檚 motion on Friday to disqualify Lester included a request to prevent the release of the tapes, which was denied. In a statement released Monday, he said the defense 鈥渨ill victoriously defend鈥� Zimmerman against the allegation and promised to release new information regarding the accuser鈥檚 statement 鈥渋n the next several weeks.鈥�

Zimmerman is currently out on bond. His travel is restricted within Seminole County and he is barred from the local airport. He is required to wear an electronic monitoring device and is not allowed to drink alcohol.聽