When he bought the team in 1989 his first move was to get rid of one of the most successful coaches in the NFL in Tom Landry.
His next move was to force out equally well respected General Manager Tex Schramm in order to assume those duties himself. Since he took on that mantle he has never relinquished it, making him the NFL's longest tenured GM and the only owner/GM.
But he has more credentials to be a general manager than almost any other owner out there. With the notable exception of Jerry Richardson the owner of the Carolina Panthers who played two seasons for the Baltimore Colts, Jones is the only owner with a football background at a high level.
Jones was an All-Southwestern Conference offensive lineman on the 1964 National Champion, Arkansas Razorbacks football team. So when he assumed the duties of GM fans would know that he knew what he was looking at.
Jones had considerable success. Two years after he took over the Cowboys ended their longest playoff drought ever (five years) when then won an NFC wild card berth in 1991. Jones made the playoffs for six straight years and won three Super Bowls over that stretch with players like Troy Aikman and Emmett Smith (both were his draft picks).
But, since their last Super Bowl title 16 years ago, the Cowboys are just 2-7 in the playoffs and the team has missed the postseason all together in nine of those 16 years. The team is just 130-126 since they lost hoisted the Lombardi trophy, but they have also watched hated rivals like the Giants win two Super Bowl rings.
But his problem hasn't just been a lack of success, it has been a legacy of questionable decisions by Jones that have gotten the Cowboys to this place. He has a propensity to fall for flash and not substance, which has caused the Cowboys to be a lot of sizzle with very little steak.
His current quarterback Tony Romo, embodies that. In his six seasons as an NFL quarterback he has amassed amazing stats. He has 96.9 career quarterback rating, which is second in NFL history behind only Aaron Rodgers.
Romo has led 13, fourth quarter comebacks and 14 game winning drives but he is only 48-36 as an NFL starter.
Romo looks the part of a great NFL quarterback, he even manages to put up the numbers of a great NFL quarterback, but unlike the true greats he seems to make silly mistakes as often as he makes the right choice.
Jones' defense is similarly embodied by players like DeMarcus Ware or Roy Williams. Ware is an ungodly pass rusher, but he can't find himself in coverage and isn't even much of a run stopper as evidenced by his woeful tackle numbers year in and year out.
Williams has retired, but he was an example of Jones getting caught up in a single flashy element. Williams could light up receivers with the big hit and the Cowboys were so enamored of that skill that they never seemed to notice that he was far too slow to make use of those skills.
His career is best known for his excessive use of horse collar tackles as he desperately tried to catch receivers who were much faster than them.
Wrapped up in his tendency to go for flash over substance is Jones' tendency to outsmart himself. The Cowboys roster is littered with players who were castoffs with other organizations or sometimes even other sports. Yet Jones often thinks he can make it work.
From former Lions wideout Roy Williams to Terrell Owens and Adam Pac-Man' Jones, Jones loves to try to show how smart he is by grabbing castoffs and trying to show them the Cowboy way.
Former quarterback Drew Henson was the ultimate example of this. Henson became the Cowboys quarterback after the New York Yankees discarded him as a third baseman prospect. Although, Henson played quarterback for Michigan in college, investing in him was a strange, high profile move that never paid off.
Even in the 2012 draft, where he was lauded for moving up to take cornerback Morris Claiborne, there were reasons to question him. The Cowboys had more holes than just cornerback and perhaps the Cowboys would have been better off drafting more depth instead of the one star player.
Jones has been an integral part of the game for the past 22 years and few owners have ever done so much for the game of football, but as a general manager his time has passed and he would do well to step back and look for help elsewhere.