The case opens in 1996. Spike Lee needed a red Yankees hat to match his Starter jacket for Game 3 of the World Series. No such hat existed. MLB teams wore their colors and only their colors.
So he called New Era CEO Chris Koch. Koch was willing, but the only way it was happening was if George Steinbrenner said yes.
Lee called him. His argument: the red is for the jacket, not for Boston. Steinbrenner said yes. New Era made the hat. Spike wore it to the game. The photographs spread everywhere.
"When Spike wore the 59FIFTY red Yankees cap to Game 3 of the World Series, what followed became a defining moment in culture, officially merging sportswear and fashion."
Demand exploded. New Era started producing hats in colors that had no relationship to team uniforms. Lifestyle colorways eventually became roughly half of New Era's entire business.
Thirty years later, in May 2026, New Era marked the anniversary with a seven-piece collection. The red hat came back with Lee's signature on the gray undervisor and a commemorative side patch. Jazz Chisholm Jr. wore it to a game in the Bronx to honor it. A current Yankee wearing a hat that exists because a director called an owner about a jacket in 1996.
Every alternate colorway, every non-traditional palette, every hat on the deals feed that looks nothing like what a player would wear on the field -- it all traces back to one phone call and one yes from The Boss.
Steinbrenner had no idea what he was approving.
- Hatlock