Citations:
1947 The Progress (Clearfield, Pa.) (Nov. 28) “Osceola Redskins Repeat Over Legion, 14-0” p. 6: Rafferty, Latz, the Jaskowak brothers and Water played headsy ball for the invaders. 1975 Rich Cullen Daily Times (Salisbury, Md.) (Oct. 26) “Field Goal In Last 4 Seconds” p. 16: W & J, 5-1 entering the game, appeared unbeatable in the first half with headsy–smart football. 1984 AP (May 5) “Sports News” (in Toronto): First baseman John Wathan charged in to take control and flipped to the now-recovered Royals right-hander, but Griffin had already made his successful lunge for the base. “Headsy play,” said Stieb, the ace right-hander and winner of his fifth straight game without a loss thanks to Griffin’s unexpected move. 1986 Ted Castillo Baton Rouge Morning Advocate (7D) (Sept. 19) “Central turns back Catholic”: Abadie is a headsy player. He checked off and made the call himself on that play. 1992 Warren Hinckle Deadly Secrets (Nov.) p. 96 @ (Nov., 1993): The President says no deal.…I guess well have to be headsy-headsy about this. 1995 Evan Thomas The Very Best Men (Oct. 20) p. 258 @ (Dec. 10, 1996): He was always urging agency men to be “headsy” and “forward leaning.” 1998 Pat Summitt Raise the Roof (Nov. 3) p. 97 @ (Oct. 5, 1999): Ace calmly stepped in bounds, picked the ball up, and got a shot off. It was a smart, headsy solution. 2005 Katie Thomas Newsday (Long Island, N.Y.) (Dec. 27) “A teen, his drive & his goal”: In coaching parlance, Scott was “headsy,” Drummer said. “He could see the court, understand what’s going on, and take advantage of what opportunities the other team is giving you.”
Reader comments:
Probably derived from “heads-up” = ‘alert, resourceful’ (dated to 1947 by MWCD11).
I think so too, with reinforcement from “gutsy” and “ballsy.”