Everything about Dave Winfield in this picture is cool. Let’s examine this more closely:
1. Hat perched on his head. I get the feeling he could wear it inside out and it would still look cool.
2. No jersey on under that slick Yankees jacket, just a t-shirt.
3. The look. That look says it all. “I’m Dave Winfield, I can do anything I want, and I’m definitely better than you. Probably not just at baseball, but life too.”
Things were shitty with the Yankees for Winfield by 1989, but brighter days were ahead for him, including a World Series win with Toronto in 1992, with Winfield getting the game-winning RBI in the decisive game six. Maybe that’s why he looked so cool. He knew things were going to get better.