Giuliani managed only to keep company officials out of jail. In a plea agreement in May 2007, Purdue Pharma and the three executives pleaded guilty to misleading doctors and patients. They paid a total of $634.5 million in penalties and fines.
Even thornier legal challenges may lie ahead for Giuliani.
In spring 2005, he joined a politically connected Houston-based law and lobbying firm as senior partner. He opened a New York office for the firm, which changed its name to Bracewell & Giuliani, and began representing clients.
Federal records show the firm is paid to lobby Congress, key regulatory agencies and the departments of Defense, Justice, Energy and State on behalf of defense contractors, oil and gas conglomerates, tobacco companies and other clients. The firm is registered to lobby on nuclear waste disposal, trade policy, stem cell research and other concerns.
Overseas, Bracewell & Giuliani operates a satellite office in oil-rich Kazakhstan. The firm has helped rewrite the country's tax code to lure foreign investment, officials said. The U.S. State Department last year described the ruling regime's human rights record as "poor," with reports of arbitrary arrests, torture, press censorship and other abuses.
If elected president, Giuliani could face conflicts of interest when those issues cross his desk. He has declined to discuss his work for the firm that bears his name.
"People are going to ask questions about what he was paid for," said Sarah Dufendach, vice president of Common Cause, a nonpartisan government watchdog group.
The anthrax case in Florida remains a sore point for Giuliani.
Shortly after Sept. 11, letters laced with anthrax spores arrived at the offices of media companies in New York and of two U.S. senators in Washington. But the first such letter had gone to the Boca Raton headquarters of American Media Inc., publisher of supermarket tabloids.
An AMI photo editor and four people in other states died of anthrax infections. The bio-attack closed Senate and other government offices for weeks, crippled mail service for months, and terrified a nation still traumatized by the Sept. 11 attacks.
The crime remains unsolved.
AMI sold the quarantined building to a local developer, David Rustine, for $40,000 -- a fraction of its previous value. The new owner searched for a company to handle the estimated $5-million cleanup.
