Legendary talk show host David Letterman sports Winnipeg Blue Bombers toque

Photo courtesy: Netflix

It appears as though the Winnipeg Blue Bombers have an extremely famous fan.

Legendary talkshow host David Letterman was in New York City on Tuesday and was photographed sporting a Winnipeg Blue Bombers toque while signing autographs for fans. The royal blue headwear was emblazoned with the words “Grey Cup champions.”

The 74-year-old was at 30 Rockefeller Plaza to celebrate the 40th anniversary of Late Night, for which he served as the original host. Late Night with David Letterman ran for 1,819 episodes (1982-93), followed by Late Night with Conan O’Brien (1993-2009), Late Night with Jimmy Fallon (2009-14), and Late Night with Seth Meyers (2014-present).

Letterman retired from Late Show with David Letterman in 2015, completing a 22-year run that spanned 6,080 episodes. He has since sported a large white beard, even while hosting My Next Guest Needs No Introduction with David Letterman, which debuted on Netflix in 2018 (pictured).

Winnipeg won its second of back-to-back Grey Cups in December 2021, becoming the first team to repeat as CFL champions since the Montreal Alouettes did so in 2009-10. If they are able to three-peat in 2022, maybe we’ll see John Oliver and Stephen Colbert sporting similar toques come February 2023.