Most of the research on gambling behaviour among youth has been quantitative and focused on measuring prevalence. As a result, little is known about the contextual experiences of youth gambling, particularly among those most vulnerable. In this paper, we explore the previous experiences of youth gambling in a sample of adult men experiencing housing instability and problem gambling. We present findings from a qualitative study on problem gambling and housing instability conducted in Toronto, Canada. Thirty men with histories of problem or pathological gambling and housing instability or homelessness were interviewed. Two thirds of these men reported that they began gambling in youth. Five representative cases were selected and the main themes discussed. We found that gambling began in early life while the men, as youth, were also experiencing adversity (e.g., physical, emotional and/or sexual abuse, neglect, housing instability, homelessness, substance addiction and poverty). Men reported they had access to gambling activity through their family and wider networks of school, community and the streets. Gambling provided a way to gain acceptance, escape from emotional pain, and/or earn money. For these men problematic gambling behaviour that began in youth, continued into adulthood.