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Defense attorney J. Tony Serra is heading back to prison for failing to pay taxes. U.S. Magistrate Judge Joseph Spero sentenced the renowned criminal trial lawyer to 10 months on Friday. It’s the third time Serra has been convicted for tax problems and is the harshest sentence he’s faced so far. Serra’s attorney, Randolph Daar, said he was disappointed. “The judge felt that the repetitive nature of the conduct justified the sentence,” Daar said. “I guess it’s a real sad way to waste a jail bed. It’s an exercise in futility or vindictiveness.” Serra got off easy the last time he was convicted for not paying taxes in 1986, when he got probation. In 1974, he served four months in Lompoc federal prison — after which he emerged as defiant as ever. Serra bragged that he was able to continue doing legal work while incarcerated, and he recommended the experience to other defense attorneys. But things could be different this time. Serra, 70, recently had hip-replacement surgery. This time around, Daar argued that Serra could actually be in danger behind bars. Serra has repeatedly attacked government informants over the years, and “there is concern that [he] would be targeted by angry snitches,” Daar wrote in a sentencing memo filed several months ago. Prosecutors from the U.S. Department of Justice’s tax division in Washington, D.C., filed two misdemeanor counts earlier this year alleging Serra failed to pay $18,037 in 1998 and $26,495 in 1999. He pleaded guilty in April, admitting he hasn’t paid taxes since 1991. Instead of going to prison, Daar suggested Serra be sentenced to home detention and noted he has agreed to pay $100,000, which will be donated by friends and supporters. Daar said Serra refused to pay taxes not because he’s greedy but because of his “dysfunctional relationship to money.” Serra has taken an informal vow of poverty, eschewing material possessions and doing much of his work pro bono, Daar argued. Government prosecutors had recommended 12 months. Serra had hoped to avoid taking time away from his busy trial practice to resolve the case and has already made an agreement with prosecutors to begin serving the sentence in January. Serra is currently in the middle of a trial in Hayward, Calif., where he is defending one of the young men accused of killing transgender teen Gwen Araujo. Even though Serra is upset, Daar said he’s trying to remain positive. After the probation department recommended five months in prison, Serra said he would be able to write two books. Now, he’ll just have to do four, Daar said. The DOJ’s tax division also did not return a call. The case is U.S. v. Serra, 05-00171.

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