20. Ray ‘Sugar’ Williams
Ray ‘Sugar’ Williams, an ex-NBA star with the Knicks and Celtics, faced bankruptcy in 1994, post-retirement. By 2010, he was homeless, questioning the loyalty for struggling ex-players while current salaries soared, living out of his 1992 Buick.
In a tale of solidarity, Kevin McHale and Larry Bird, former teammates, reached out with financial aid to Williams. Despite their efforts, Williams’s journey ended when he lost his battle with cancer at 58.
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