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Montgomery Blair Sibley says he litigates “like a hurricane,” and he certainly has left a lot of legal wreckage in his wake. If you cross him, he’ll probably sue you. Just ask his ex-wife, Florida prosecutors, or even Supreme Court justices, whom he sued for treason. Sibley, 50, now represents the infamous Deborah Jeane Palfrey, who is accused of running a high-end D.C. prostitution ring. Sibley was brought in to recover more than $1.5 million in assets seized as part of the government’s criminal investigation. While Palfrey’s court-appointed criminal defense attorney has avoided headlines, Sibley has basked in the limelight, threatening to sell Palfrey’s 10,000-plus client list to pay her legal bills. Why Palfrey would tap Sibley as her civil forfeiture lawyer remains a mystery, given that he’s lost more cases than some lawyers ever file. He has been sanctioned by multiple courts in Florida, where a state appeals court found that he was “an unending source of vexatious and meritless litigation.” His most notable legal battle was highly personal: an acrimonious divorce case that once put him behind bars for 77 days when he failed to pay more than $275,000 in child support. And he still could face disciplinary action in Florida over two bar complaints. Sibley’s tactics are simple: When he doesn’t win, he sues. He’ll sue the judges, the prosecutors, the witnesses, and the courts. And he’ll appeal again and again and again. “I litigate like the Miami Hurricanes play football,” says Sibley, who calls himself a leader in forfeiture law. “I litigate like a hurricane.” STORMING THE COURTHOUSE In recent weeks, Sibley has swept through the U.S. District Court for the District of Columbia, triggering the ire of prosecutors and adverse rulings from the presiding judge in Palfrey’s case. Palfrey, who lives in California, was indicted March 1 on five counts of racketeering and money laundering for an alleged prostitution ring of beautiful, college-educated women servicing wealthy clients. Palfrey, who was convicted on similar charges in the 1990s in California, says her D.C. business was only an escort service. Sibley’s strategy has been unusual from the get-go. His work began in October, when the government froze Palfrey’s bank accounts and seized her property, including two California houses. In his challenge, Sibley made several arguments claiming the seizure was illegal. One was that D.C.’s laws against prostitution are too vague. “The man knows how to write, but I think the issues he is raising are pretty far out,” says David Smith, a lawyer who wrote a leading textbook on forfeiture law, after reviewing Sibley’s motion. But Sibley didn’t stop there. He sued two financial institutions holding Palfrey’s funds, accusing them of violating wiretap laws by providing records to investigators. He also attacked prosecutors, who say Sibley threatened to write to Attorney General Alberto Gonzales asking for a special prosecutor in the case, according to court documents. Even when the criminal indictment came down, Sibley asked the court to keep moving forward with the civil forfeiture case, despite concerns from Palfrey’s court-appointed defense attorney, A.J. Kramer, head of the D.C. Office of the Federal Public Defender, who was wary of exposing Palfrey to depositions while she still faced criminal charges, court documents state. But probably Sibley’s most bizarre move was when he vowed to sell his client’s list of customers, which many speculated contained the names of prominent politicos. At a press conference on the courthouse steps after Palfrey’s March 9 arraignment, Sibley touted his many offers. Government lawyers fired back, arguing that any proceeds could also be frozen. Ultimately, Judge Gladys Kessler barred Sibley from selling the list, but not before he gave it to an unnamed news organization, which has yet to publish any names. On March 9, Kessler stayed the forfeiture case while the criminal case proceeds. Undeterred, Sibley filed another suit on Palfrey’s behalf the same day, this time accusing former Palfrey employee Pam Neble of breaching her employment contract by engaging in illicit sexual acts with customers. It was a trademark move. Last year, Sibley filed a similar suit against former employees of convicted Florida pimp Arthur “Big Pimpin’ Pappy” Vanmoor, alleging they violated their contracts by engaging in sexual acts. On Vanmoor’s behalf, Sibley also sued witnesses, as well as the financial institutions and prosecutors involved in the forfeiture of Vanmoor’s accounts. All of the suits were dismissed, except two suits that remain pending. In Palfrey’s case, government lawyers accused Sibley of “witness intimidation and harassment.” On March 22, Kessler issued a temporary restraining order, halting the suit against Neble and barring any more lawsuits against Palfrey’s former employees. Sibley scoffs at these allegations. “What difference does it make what I’ve done in other lawsuits to the determination of the facts in this lawsuit?” he says. “It’s an ad hominem attack, the lowest form of attack known to man. It’s not surprising that’s the attack the U.S. attorneys use because they cannot succeed on their motions for reasons I will make painfully clear to them.” TRACING HIS ROOTS Born to a family that traces its roots to George Mason, a Founding Father who helped shape the Bill of Rights, Sibley’s family tree doesn’t branch far from the establishment. His maternal great-great-great-grandfather was Montgomery Blair, postmaster general for President Lincoln and namesake of the Silver Spring, Md., high school. The Pennsylvania Avenue Blair House, where presidential guests stay, once belonged to Sibley’s family. On his father’s side, he traces his lineage to Hiram Sibley, founder of the Western Union Telegraph Co. His grandfather Harper headed the U.S. Chamber of Commerce during the New Deal era. (For the record, Sibley is not related to the namesake of Sibley Hospital.) Yet Sibley sees himself as a David fighting the Goliath he calls the judicial system, and he draws on the example of his ancestor Montgomery Blair, who was criticized for representing Dred Scott in the landmark 1857 Supreme Court case declaring that blacks could not be citizens. Sibley grew up in Rochester, N.Y., one of six siblings. “We’re a big family, but nobody is crazier than Blair,” says Harper Sibley Jr., Sibley’s father and now a prominent South Florida developer. Sibley played rugby and several other sports with so much aggression that his father often picked him up from the hospital. Sibley’s ambitions soon turned to the law. He graduated from the University of Miami and later from Albany Law School at Union University, returning to his hometown district attorney’s office as a prosecutor for the next five years. After losing his bid for district attorney in 1987, Sibley headed to Miami. Sibley has also had trouble at home, including a bitter 1994 divorce from his first wife, Barbara, with whom he had three children. Their initial custody agreement put the children with Sibley during the week in Miami and with their mother on the weekends in Key Largo, court records state. But the divorce soon turned into an affair worthy of TV drama when, a few years later, Sibley decided to follow his second wife (with whom he’d had another son) to Washington. Sibley hoped to take his three other children, but Barbara objected. Whenever the family court ruled against Sibley (which it almost invariably did), he would appeal, vowing to fight down to his last dime. “If you want to attempt to squeeze me until I am dry, we will litigate until I am disbarred and bankrupt if necessary, for you leave me no other choice,” Sibley wrote his wife, court records state. In total, Sibley filed more than 25 appeals with the family court. He also initiated at least a dozen suits in federal court against judges, the court system, and his former wife, according to one court opinion. He prevailed in one early appeal, but judges threw out the rest. His style has won him notoriety among those who faced him in his never-ending litigation. But even his opponents note Sibley has always been professional and cordial in court. Many seem more amused that he often wears kilts, which Sibley says show his Scottish roots. He owns seven in various colors. “He’s a very unique lawyer,” says Isidoro Rodriguez, an attorney who has worked with Sibley in the District. “He’s unwilling to give up, which I admire.” Sibley’s divorce case came to a head in August 2002, when the family court judge, Maxine Cohen Lando, told Sibley he’d face jail time if he did not ante up his long-overdue child support. The court ordered him to pay Barbara more than $100,000 and another $175,000 for the children’s private-school tuition, giving him a Jan. 1, 2003, deadline. According to Lando’s opinion, Sibley had hidden his assets by transferring them to his second wife. (At the time, Sibley said they were estranged. They are now divorced.) And, Lando wrote, his income was far greater than he reported because his father subsidized his expenses. Unsurprisingly, Sibley objected, claiming his income was only $37,500. Seeing no progress, Lando held Sibley in contempt in November 2002 and sent him to jail in Miami-Dade County. “It was a way to brutalize me,” says Sibley, who was imprisoned for more than two months. After his release, Lando gave Sibley two months to make good on his child support, but by April, Sibley still hadn’t budged. Lando ordered him, once again, to jail. This time, Sibley’s father bailed him out and paid $100,000 of his child support. But because the judge never rescinded her contempt order, Sibley took the strange move of filing a petition for unlawful imprisonment, even though he was free. That petition ultimately was dismissed. Sibley’s fight was far from over. He still owed his ex-wife more than $33,000 from a separate judgment. In January 2004, a different judge held Sibley in contempt again and ordered that he be barred from filing any more documents with the court pro se. A Florida appeals court and the Florida Supreme Court concurred. But Sibley continued his challenges, moving up the pecking order of judges. In 2004, he sued three judges on the U.S. Court of Appeals for the 11th Circuit and all of the Supreme Court justices for violating his rights by denying cert and for committing treason. He sought $1 million in damages in Florida federal court. When that claim failed, Sibley tried again in D.C. federal court, seeking just $75,000. Last fall, that claim was dismissed. These challenges led the Florida Bar to investigate two complaints against Sibley for his litigiousness and for failing to pay child support. Those complaints are still pending, an attorney for the bar says. While Sibley says he expects to win on the ethics complaints, they already have caused him some headaches. After passing the bar exam in Maryland, where he has an office, he was denied admission until the Florida grievances are settled. (He already is a member in good standing of the bars in New York and the District.) Instead of waiting, Sibley filed suit in Maryland federal court, alleging the decision violated his constitutional rights. The case, like so many others, was dismissed. Despite his ongoing bar complaints, Sibley made a bid for president of the Florida Bar. He’s also organizing a ballot initiative seeking to amend the Florida state constitution to allow legal challenges against judges. But as Palfrey’s case runs its course, the question remains: Which Miami Hurricanes team will Sibley mirror — the 2001 national champions, or the team last year that posted one of its worst seasons in recent history?
Emma Schwartz can be contacted at [email protected].

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