A man who sent billions of junk e-mails hawking online college degrees, sexually explicit Web sites and "generic Viagra" must pay more than $5 million in penalties to America Online Inc., a federal judge ruled.

Christopher William Smith, of Prior Lake, Minn., was considered one of the world's worst spammers, operating under the name Rizler. He is now in a Minnesota jail awaiting trial on criminal charges that he violated federal drug laws while operating an online pharmacy.

On Tuesday, U.S. District Judge Claude Hilton ordered Smith to pay $5.3 million in damages and $287,000 in legal fees to AOL, which filed a civil suit against Smith under a 2004 federal law known as Can-Spam.

AOL spokesman Nicholas Graham said Smith "was the poster child for the Can-Spam Act."

"This is someone we've been pursuing for three years," Graham said. "It's one of the largest judgments we've received."

Hilton issued a summary judgment in favor of AOL, saying Smith "refused to participate in this case, willfully disregarding ... discovery obligations and failing to comply with multiple court orders."

Court records show that Smith's lawyers withdrew from the case several months after it was filed.

In addition to e-mails promoting generic Viagra and pornographic Web sites, Smith also advertised cable TV descramblers and penis enhancement pills.

In an initial response to AOL's lawsuit, Smith's lawyers denied wrongdoing and questioned the constitutionality of the Can-Spam law.

Graham said that AOL, the Dulles-based subsidiary of Time Warner Inc., has won tens of millions of dollars in judgments against more than 30 spammers under the federal law and a similar Virginia law.