In the early to mid 1990's, Reggie Miller, a three-point-shooting, trash talking performance artist gave the entire city of New York “the finger.” Dominating the game’s biggest stage, Madison Square Garden, he did the unthinkable. He managed to humble superfan and antagonist Spike Lee, shut up Rudy Giuliani, force the Armani-clad coach Pat Riley into retirement and push Knick heroes Patrick Ewing and John Starks to the brink of psychotic breakdowns. In Winning Time: Reggie Miller vs. The New York Knicks, a rich, dark operatic comedy (68 minutes running time), Peabody award winning director Dan Klores explores much more than Miller's historic playoff performances (logging 25 points in the fourth quarter of Game Five in 1994, eight points in the final nine seconds of Game One in 1995). Klores exposes two powerful forms of resentment that helped craft the NBA's last great rivalry. Both Indiana and New York City took pride in being the “true” home to the sport. Theirs was good Midwestern values against liberal East Coast beliefs. It was country life vs. city life. As significant, New Yorkers detested Miller, yet, he ironically possessed all the general characteristics assigned to them. Loud, arrogant and brash, Miller personified cosmopolitan – traits that his '”Hoosier Nation” reviled.

In The Garden, Knick fans loved to chant, “Reggie Sucks, Reggie Sucks,” at the mere sight of their 6'7" string bean enemy. Those catcalls, however, only served to inspire him. It was the other taunt, the singsong of "Cheryl, Cheryl,” that spiked an emotional arrow to the superstar’s psyche, forcing him to recall and confront his lifelong insecurities. While growing up in Riverside, California, Reggie had remained in the shadow of his older sister Cheryl. She was a rough, loud, tough, eight-time All-American, the greatest women’s basketball player in history and a sibling he could never defeat. To Reggie Miller, the Knicks and the grand stage of NYC represented, "Cheryl all over again,” setting up Knick fans and players in an unfamiliar role…losers.

The operatic score is mixed with songs from such rock ‘n’ roll legends as Dion and Paul Simon. Interviews with Patrick Ewing, Pat Riley, John Starks, Larry Brown, Marv Albert, Ahmad Rashad, Cheryl Miller, Jeff Van Gundy, Pete Vecsey, Donnie Walsh, Byron Scott, and many others color the piece.