i don't know, if he's really trying to win a SB he sucks at it. If he's trying to keep the team relevant and keep the cash flowing in like many believe, he's very good at that as of late.
Even if the Cowboys do win a Super Bowl between 1996 and 2026, enough seasons will have passed to make a championship nothing more that the Law of Averages being satisfied.
The odds say that very team should win a Super Bowl during a 32 season span.
In other words, a single Super Bowl championship does nothing more than reinforce the team's record of mediocrity during that period.