Wall Street 2: Money Never Sleeps. Michael Douglas is back in his Oscar®-winning role as one of the screen’s most notorious villains, Gordon Gekko. Emerging from a lengthy prison stint, Gekko finds himself on the outside of a world he once dominated. Looking to repair his damaged relationship with his daughter Winnie, Gekko forms an alliance with her fiancé Jacob (Shia LaBeouf). Jacob and Winnie must decide if they can really trust the ex-financial titan, whose relentless efforts to redefine himself in a different era have unexpected consequences.