Priest Holmes case might've been helped or strengthened if his Chiefs during his prime 3-year run had won a few post-season games or he appeared in a SB. I know he won a SB with Baltimore back in 2000, but he wasnt the featured, every-down, workhorse RB who got most of the carries (that would be Jamal Lewis). At that particular point in his career development, his role was similar to Michael Turner in San Diego behind L.T. before being picked up by Atlanta and beginning his own, successful career as a Pro-Bowl RB from 2008-2013.
At least as a featured, MVP-CALIBER duel-purpose RB, Priest's best chance to make a Super Bowl with the Chiefs was in 2003 and unlike K.C. today under Reid and Mahomes, those Chiefs tended to have great regular-seasons and seem nearly unbeatable, then become ultra-conservative, mistake-prone or badly-coached squads in the playoffs or like in 2003, their defense was non-existent and ended up losing a wild, high-scoring shootout against a strong, sturdy resurgent Colts team.
Kansas City under Schottenheimer and then Dick Vermeil were one of the winniest teams from the late 80's-mid 2000's, but only had 3 post-season wins to show for it. From 1993-2015, Chiefs didnt have a single post-season win despite making the playoffs (1994, 95, 97, 2003, 2006, 2010, and 2013) seven times over the same time period along with several other non-playoff winning seasons (96, 99, 2005, and 2014).