Is it time for Craigslist Inc. to bring a lawyer on board? Until recently the question might not have seemed pressing. The San Francisco-based company has enjoyed a magical ride along the information superhighway, making millions from its online classified ads. But in April the pavement suddenly got rough. Craigslist was sued by its minority partner, the Internet auction giant eBay Inc., then quickly countersued. Now some observers wonder whether the company needs an attorney riding shotgun.

Craigslist founder Craig Newmark and CEO Jim Buckmaster declined to answer questions about the company’s legal affairs, but the subject is clearly on their minds. Asked in May by Management Today what he dislikes most about his job, Buckmaster replied: “Inquiries from the law aren’t pleasant.”