Now it appears McFadden's latest hamstring injury might have soured the organization on his potential once and for all.
Steve Corkran of Bay Area News Group wrote Tuesday that he can't even envision general manager Reggie McKenzie extending an offer to McFadden prior to the start of free agency in 2014.
As McFadden's fill-in, Jennings has more rushing yards over the past five weeks than any running back except Adrian Peterson. Quite simply, Jennings has outplayed McFadden in offensive coordinator Greg Olson's offense.
NFL Media Insider Ian Rapoport reported last August that McFadden rejected the organization's contract overtures. He was intent on proving that he could stay healthy and productive on his way to one last mega-contract the next offseason.
That gamble has backfired. The Raiders seem more inclined to lock up Jennings at a bargain rate while allowing the injury-prone McFadden to test his value on an open market that rarely pays for veteran running backs.
In a best-case scenario, McFadden will land a contract in the neighborhood of Reggie Bush's four-year, $16 million contract. It's not hard to imagine him turning his career around if he finds himself in a situation similar to Bush's in Detroit.