These Horny Emails May Have Gotten Former NBA Player Winston Bennett Fired From His Government Job
Photo: Mike Powell/ [object Object] Former Kentucky basketball star Winston Bennett was fired from his position as director of the state labor cabinet’s division of apprenticeship last month, after just 10 weeks on the job. No reason was given for the firing, but the Louisville Courier-Journal used a public records request to get ahold of the emails he sent while employed by the state, and the messages that he sent to female colleagues in the days before he was terminated are... something.
Here’s Bennett—who was drafted by the Cavaliers in 1988 after four years at Kentucky and then played three seasons in the NBA—telling one female coworker what he thought about her:
“Too hot to trot. Especially on those skirt and dress days, lips stick matching. Lord have mercy. LOL!!! Not too old by a long shot.”
Three exclamation points after LOL to let you know that it’s really funny. (But not, like, LMAO levels of funny: that’d be inappropriate.)
Here’s another one:
“I just want to say you are a wonderful lady and I enjoy speaking with you. 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.”
This one’s tough to decipher, but Bennett might be saying that he hopes his compliment does not cause her to become complacent and let herself go, on account of how impressionable she is. There’s also a chance that he misused “impressionable” and instead meant to write “impressive.” Or “impeccable.” Or, uh, “impenetrable”?
Shortly before he was fired, Bennett had an email conversation with a woman where he commented on what she had worn the day before and asked what she did “for excitement” after work. She responded: “Not a lot. On a serious note. Delete these email, because from time to time they check people’s mail.”
Two days later, he was dismissed from his position. The labor cabinet would not comment to the Courier-Journal about the specific reason for the firing, but they confirmed that there had not been any formal complaints filed about Bennett’s behavior and instead said simply that they had “became aware of a potential issue” and let him go.
Bennett has publicly admitted before that he’s struggled with sex addiction. He worked under Rick Pitino as an assistant coach at Kentucky beginning in 1995, and he followed Pitino to the Boston Celtics in 1997—but he was fired in 1998, for what he later described as problems that arose from his sex addiction.
h/t George
Everything to Know About the 2025 NBA Cup Quarterfinals
Next Big Stars in WWE: Watch These 2026 Breakout Stars
The AFC Is Wide Open Heading Into Week 15
Kansas City Chiefs Need Offensive Changes This Offseason
- Eagles vs Chargers Monday Night Football Betting Prediction: Week 14 Bet Picks
- NBA Best Bets Today: Sunday Dec. 7th Top NBA Picks
- Texans vs Chiefs Sunday Night Football Betting Prediction: Week 14 Bet Picks
- Top 10 NFL Player Props for Week 14: Best Bets and Expert Picks
- College Football Conference Championship Best Betting Picks, Predictions
- UFC 323 Betting Picks: Best Bets for the Final ESPN Pay-Per-View
- NBA Best Bets Today: Top Betting Predictions for Friday Dec. 5th

