- Attended South Kitsap High School in Port Orchard, Washington. (Class of 1988)
- He is older than David Lee Hefner by 2 minutes.
- Identical twin brother of David Lee Hefner.
- Son of Tom Hefner and Leah Hefner.
- Brother-in-law of Jenny Hefner.
- Is ambidextrous.
- Grandson of Harold Hefner.
- Shares the same middle name (Winston) as his father, Tom Hefner and grandfather, Harold Hefner.
- Older brother of Mike Hefner.
- Drives a Hummer H3. He was one of the earliest adopters that equipped his vehicle with both a rear Back-Up Camera and a Dash Camera - several years before car manufacturers began to include them and long before becoming mainstream.
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