Fired Kentucky basketball star sent lewd emails to women

Former Kentucky basketball captain Winston Bennett was named director of the state’s Labor Cabinet’s Division of Apprenticeship on August 1 but was fired last month 

A former University of Kentucky basketball player was fired from his job in the state’s Labor Cabinet last month after sending personal emails to women on his government computer in which he commented on their appearance. 

Winston Bennett, who also served as an assistant coach with the Wildcats after a brief NBA career, allegedly told a cabinet employee she was ‘Too hot to trot,’ according to emails obtained by The Louisville Courier Journal under the Kentucky Open Records Act. 

‘Too hot to trot,’ Bennett wrote to a cabinet employee. ‘Especially on those skirt and dress days, lips stick (sic) matching, Lord have mercy. LOL!! Not too old by a long shot.’

Bennett, who began his job on August 1, was given no reason for his firing as director of the Labor Cabinet’s Division of Apprenticeship.

Bennett, 52, didn’t return the newspaper’s phone messages seeking comment.

Labor Secretary Derrick Ramsey’s chief of staff, J. Brooken Smith, said no written complaints were filed with the cabinet but that when a potential issue surfaced, Bennett was terminated.

A former 'Mr. Basketball' in the state of Kentucky, Winston Bennett was named the Wildcats captain in 1988 before averaging 15.3 points and 7.8 rebounds a game as a senior

A former ‘Mr. Basketball’ in the state of Kentucky, Winston Bennett was named the Wildcats captain in 1988 before averaging 15.3 points and 7.8 rebounds a game as a senior

Seven women who work in the cabinet declined to comment.

Bennett reportedly had a $73,500 annual salary before being fired.

‘I just want to say you are a wonderful lady and I enjoy speaking with you,’ Bennett wrote in another email. ‘I also want to say you look very nice today. I hope my saying this does not mess up your shape, kind like eating a cup cake. You are very impressionable. Have a wonderful day.’

In an email conversation dated October 10, Bennett asked what another woman did ‘for excitement,’ adding that he liked to be called ‘Winnie.’

Winston Bennett (far right) worked under former Kentucky coach Rick Pitino (center left) as an assistant coach for the Wildcats from 1995 until 1997, when he followed Pitino to the Boston Celtics 

Winston Bennett (far right) worked under former Kentucky coach Rick Pitino (center left) as an assistant coach for the Wildcats from 1995 until 1997, when he followed Pitino to the Boston Celtics 

‘Not a lot,’ the woman replied. ‘On a serious note. Delete these email, because from time to time they check people’s email.’

Bennett was fired within 48 hours, according to the Courier Journal.

Kentucky Labor Secretary Derrick Ramsey’s chief of staff J. Brooken Smith declined to tell the Courier Journal why Bennett was fired.

‘We do not comment on personnel matters,’ Smith wrote in an email to the Courier Journal. ‘To the extent you are asking about the administration’s policy on sexual harassment generally, it is clear: sexual harassment in any form will not be tolerated.’

No written complaints were filed, according to the Courier Journal.

‘As soon as we became aware of a potential issue with Mr. Bennett, it was addressed immediately and he was terminated,’ Smith said in an email. 

Bennett was named Kentucky’s team captain in 1988 before averaging 15.3 points and 7.8 rebounds a game as a senior for the Wildcats. 

He would go on to a brief professional career that included stints with the NBA’s Cleveland Cavaliers and Miami Heat before working under former Kentucky coach Rick Pitino with the Wildcats from 1995 until 1997, when he followed Pitino to the Boston Celtics. Bennett also served as the head coach at Kentucky State and Mid-Continent.

Winston Bennett goes for a rebound during a brief stint with the Cleveland Cavaliers in 1990 

Winston Bennett goes for a rebound during a brief stint with the Cleveland Cavaliers in 1990 



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