In Helena, Carson Woodland, a Realtor, briefly took on the role of a pawn broker and short-term loan provider during an exercise focused on reentry for incarcerated individuals. The event, organized by Helena’s Chamber of Commerce and Leadership Montana, was led by Katie Weston, the Montana Women’s Prison warden. Participants enacted the challenges faced by those recently released from prison, such as attending treatment sessions, buying food, securing transportation, and undergoing vocational rehabilitation. Over four simulated weeks, they dealt with limited resources and the task of completing essential paperwork.
Woodland managed a pawn shop and short-term loan table, where resources like “bus tickets” and money were scarce, highlighting the urgency of financial management for reentry success. He noted the eye-opening experience resembled a game of Clue, but with a significant underlying message about privilege. Weston emphasized the high recidivism rate, approximately one-third, and the heightened risk of homelessness among formerly incarcerated individuals, who are ten times more likely to be homeless than those without a criminal past.
Weston, with experience conducting around 50 such events, observed frequent attempts by participants to circumvent rules, mirroring real-world struggles faced by ex-prisoners. The simulation began with obtaining identification, crucial for accessing further services, and each simulated week was limited to 20 minutes, much of which was spent in lines. Transportation difficulties were evident, especially in smaller cities like Helena, lacking extensive mass transit systems.
Helena’s rising homelessness issue was also addressed, as Sarah Roope from Leadership Helena emphasized the event’s role in fostering understanding among local businesses. Weston highlighted misconceptions about reintegrating individuals with criminal backgrounds, stressing trust and privacy issues in the workplace. Few participants finished the simulation successfully, with the mock “prison” filled by the end, illustrating the state’s ongoing $700 million effort to improve prison systems. Weston remarked on the fine line between freedom and incarceration, noting how even well-functioning individuals can struggle in such scenarios.




