David Rubin, the founder and ex-president of CDR Financial Products Inc., tearfully pleaded guilty on Friday to bid rigging and municipal bond contract fraud, Thomson Reuters reports. Rubin faces 10 years or more in prison, a punishment certainly worth crying over.

CDR and its executives were charged in October 2009, as part of the government’s examination of the municipal bond market, for a plot in which the company awarded the right to manage funds to investment managers in exchange for kickbacks. Sharis Pozen, leader of the U.S. Justice Department’s Antitrust Division said in a statement that “Mr. Rubin and his company engaged in fraudulent and anti-competitive conduct that harmed municipalities and other public entities.”

Rubin pleaded guilty to one count each of conspiracy to restrain trade, wire fraud and conspiracy in Manhattan federal court. CDR pleaded guilty to similar charges on Friday, and the two other charged executives are scheduled to appear in court this week.

CDR may face a $100 million fine, and Rubin, who has yet to be sentenced, will return to court on April 27.