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Despite his success, Caray's personal life was marred by struggles, including the fallout from a divorce that his young son learned about through a newspaper headline. His lifestyle also led to challenges, notably when he was struck by a car in 1968, which resulted in serious injuries yet did not deter his passion for broadcasting.
As time progressed, his health continued to present challenges. Caray suffered a stroke in 1987, but with determination, he returned to the booth. His spirit remained undeterred even through a series of ups and downs that characterized his later broadcasting years.