[2] Upon graduation from law school, Bosley was staff attorney for Legal Services of Eastern Missouri, specializing in Consumer Affairs and Utility Companies.
[6] In 2001, when Bosley ran for mayor in the Democratic Primary, he was defeated again by a wide margin, this time by Francis Slay.
In September 2014 the Missouri Supreme Court found Bosley violated various attorney rules, his conduct involving dishonesty, fraud, deceit or misrepresentation, and regarding diligence.
The Court further determined Bosley violated attorney/client trust account rules including commingling of funds, failure to keep proper records, not having funds in the trust account to cover charges (bouncing checks), and failure to deliver monies due clients.
[8] Despite more complaints from clients, the latest of which was dated March 2016,[9] the Supreme Court had restored his license on December 20 of that year after he paid $10,000 worth of damages with $25,000 were labeled as pending.