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OBJECTIVE Homelessness is a serious and increasing public health concern. Childhood maltreatment and psychiatric problems have been associated with homelessness as risk factors; however, reliance on cross-sectional studies introduces ambiguity into interpreting previous findings. This study seeks to understand whether psychiatric symptoms in part explain the relationship between childhood maltreatment and homelessness. METHODS The authors used data from a prospective cohort design study in which individuals with documented histories of childhood maltreatment (ages 0-11 years) and a demographically matched group of children without those histories (N=1,196) were followed up into middle adulthood and interviewed. Psychiatric symptoms (anxiety, depression, post-traumatic stress disorder [PTSD], antisocial personality disorder [ASPD], and alcohol and drug use) were assessed at mean age 29. Homelessness was assessed at mean ages 29, 39, 41, and 47 years. Structural equation modeling was used to test mediation. RESULTS Twice as many individuals with histories of childhood maltreatment reported ever being homeless (25.6% vs. 12.3%, AOR=2.54, 95% CI= 1.86-3.50) and past year homelessness (5.5% vs. 2.5%, AOR=2.09, 95% CI=1.31-3.43) at age 29, compared to controls. Controlling for past homelessness, psychiatric symptoms predicted future homelessness at mean ages 41 and 47. Three significant paths from childhood maltreatment to future homelessness were identified through depression, PTSD, and ASPD. CONCLUSIONS This longitudinal study with documented cases of childhood maltreatment found that psychiatric symptoms earlier in life predict homelessness. Depression, PTSD, and ASPD represent pathways through which childhood maltreatment increases homelessness risk and warrant greater attention.