Bobby Simone from NYPD Blue
It was already known by fans of the show that Jimmy Smits was going to leave NYPD Blue, but Bobby Simone was written out in the most soul-crushing way possible. Simone was left with a fatal brain infection after undergoing a heart transplant to treat a pre-diagnosed condition. The episode acted as political commentary on the U.S. healthcare system. Decades later, people are still grieving Simone's death.
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