Ottie ran a legitimate bookmakers, but used an illegal wire system, the use of which was prohibited by laws of gambling. As a result, the corrupt LAPD Vice department extorted from Ottie, allowing him to keep his business, but had to bribe them. Ottie ran a number racket for Lenny Finkelstein, and was therefore part of the Cohen Crime Syndicate. Jose Ramez, a fellow associate of Lenny, was in debt to Ottie from gambling losses.
To Ottie's annoyance and reluctance, Lenny and Ramez headed a stolen morphine distribution, and forced him to act as a supplier while taking over the gambling racket. Ottie was content to run the numbers and a clean establishment, but ended up resenting his positioning from ultimately being ordered around by Lenny and hustled by corrupt cops.
Events of L.A. Noire
While investigating the deaths of Tyrone Lamont and Cornell Tyree, Detectives Cole Phelps and Roy Earle learn from Fleetwood Morgan and Jermaine Jones of Ottie's "expansion" from gambling and into drugs. With a paper trail from the betting slips, they went to investigate Ottie's bookmakers. They found his wire service as well as morphine syrettes hidden in a slot machine, which Phelps opened with the combination of a cherry, a bell, and the word 'win'. Ottie attempted to escape, but was caught. After capturing Ottie, Phelps inspected Merlon's "wand", his antique cane, and found an I.O.U. note from Jose Ramez. During his interrogation, Ottie revealed that Lenny and Ramez forced him into their dope racket. Ottie was sent to prison for racketeering and drug trafficking.