The series received criticism from Magic Johnson and Kareem Abdul-Jabbar for historical inaccuracies. Johnson said he would not watch the series because it never depicted the Showtime era accurately, while Abdul-Jabbar referred to the series as deliberately dishonest. On April 19, 2022, Jerry West demanded a retraction from HBO within two weeks for the "cruel" and "deliberately false" depiction of him as a temperamental, foul-mouthed executive prone to angry outbursts and mood swings. A week later, HBO responded to West with the following statement: "HBO has a long history of producing compelling content drawn from actual facts and events that are fictionalized in part for dramatic purposes. Winning Time is not a documentary and has not been presented as such. However, the series and its depictions are based on extensive factual research and reliable sourcing, and HBO stands resolutely behind our talented creators and cast who have brought a dramatization of this epic chapter in basketball history to the screen." West, in turn, has said that he intends to pursue legal action against HBO for defamation, even if he has to "take this all the way to the Supreme Court." Spencer Haywood, on the other hand, called his portrayal on the series a blessing.
On September 17, 2023, it was announced that the series was canceled after 2 seasons. Although HBO has reinforced that the series is a dramatization, the series has been strongly criticized by several former NBA players and basketball historians over what they allege are significant factual inaccuracies within the storylines.
