18. Phil Jackson — New York Knicks
As a player, Phil Jackson was a quality role-player on the great Knicks teams of the 1970s. As a head coach, he revolutionized the way teams handled their players, earning the nickname “The Zen Master” as a result of his philosophical approach to dealing with the egos of NBA superstars. As a Knicks executive, he…well, he really was a great coach.
If Tracy McGrady’s Raptors jersey deserves the nod at number one for being a cool jersey from a team unfortunate enough to lose a player before he truly came into his own, then Jackson’s New York Knicks number 18 is that times a hundred (or at least that times 18). Jackson truly didn’t find his knack until well after his days with the Knicks were long gone.
Jackson’s true calling was as a head coach, winning six NBA championships with the Chicago Bulls, and later five more with the Los Angeles Lakers. He specialized in handling the egos of some of the biggest superstars in the history of the game, from Michael Jordan and Scottie Pippen with the Bulls, to Shaquille O’Neal and Kobe Bryant of the Lakers.
This is also the choice here to finally get the New York Knicks their representation on this calendar. Another timeless look that remains mostly the same to this day, the bright white jersey with simple “New York” in a slightly arching orange text outlined in blue is basketball jersey simplicity perfection.
Honorable Mention: Dave Cowens (Boston Celtics), Cedric Maxwell (Houston Rockets), Kurt Rambis (Los Angeles Lakers)