In 2068, Matsumoto became aware of Faye Valentine, a patient in cryogenic suspension and therefore having incurred a large debt. He plotted with Bacchus to con her into taking his debts on. He claimed to be her attorney from Hagas Law Firm and pretended to take an interest in her. Seeing as she had a large debt to pay for her medical bills, he planned with her to deal with the payments incrementally. Secretly, however, he named her in his will, leaving her all of his assets, which were actually only debts. One night, he pretended to be chased by a collection agency, dropped her off in the woods, and "died" in a car crash escaping the ship. She, thinking he really cared about her, accepted his assets, only to find out later that he was actually over 35 million woolongs in debt. Matsumoto disappeared and this betrayal would have a big effect on Faye's personality.
Three years later, Matsumoto had incurred a bounty on himself and was chased and captured by Jet Black. Brought to the Bebop, he saw Faye for the first time, and was promptly confronted. Faye abducted him in order to get more information about herself and about what was real about their relationship. Matsumoto said it was Dr. Bacchus' plan, and that he doesn't know any more. Then, Matsumoto had another kidnap attempt from Bacchus, impersonating the ISSP, but the real ISSP chased him off and, instead, Faye brought Matsumoto to the ISSP, his small bounty collected. 
He is visually inspired by George Clooney. The insurance company appeared to be named Totus insurance company.