Baseball's best pitcher has the most losses in a career.
Cy Young, who is ranked number one (1) in all time wins with five-hundred eleven (511) career victories,is also the all time loss leader in Major League history.Cy Young-Cleveland [NL]135, St. Louis [NL]-35,Boston [NL]-5,Boston [AL]-112, Cleveland [AL]-29 Total losses 316
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baseball-almanac.com
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Albeck1994
What word is winningest least you could do is use proper English. I got it right though despite the terrible grammar