In 2005 and following law school and his work with Shapiro, Winger became the director of basketball operations and team counsel for the Cleveland Cavaliers under Danny Ferry, who was general manager at the time.
Winger worked with LeBron James, Shaquille O'Neal, Mo Williams, and Ben Wallace while with the Cavaliers.
In 2010, Winger became the assistant general manager and team counsel for the Oklahoma City Thunder under GM Sam Presti.
Winger worked with three future NBA MVPs in Kevin Durant, James Harden, and Russell Westbrook.
Some notable draft selections, include Mitch McGary, Reggie Jackson, Steven Adams, Andre Roberson, and Cameron Payne.