Mike Fisher for 105.3 The Fan | CBSDFW.com
SAN DIEGO, CA - SEPTEMBER 29:  Dallas Cowboys owner, president and general manager Jerry Jones looks on prior to the start of the game against the San Diego Chargers at Qualcomm Stadium on September 29, 2013 in San Diego, California.  (Photo by Jeff Gross/Getty Images)

Dallas Cowboys owner, president and general manager Jerry Jones (Photo by Jeff Gross/Getty Images)

IRVING (105.3 THE FAN)  – In the immediacy of the moment, some Dallas Cowboys observers believe the five-year, $40-million extension given now-departed Jay Ratliff two years ago ranks as Jerry Jones’ worst-ever gaffe.

“Well, if I had a legal pad and could show you all the decisions I’ve made ever, it’s not the worst one I’ve ever made,” Jones said Thursday.
Jerry Jones has a personal worth of $3 billion, oversees a football team worth $2 billion and has three Super Bowl rings. So the life successes in his 71 years would seem to greatly outweigh the failures. But the old oil wildcatter is a risk-taker; failures are part of the equation.

And Jones knows it.

A few years ago, Jones voluntarily helped me with a top-10 list – or rather, a bottom-10 list – detailing the failures that stand out in his mind. Here, let’s use Jerry’s own “legal pad’’ to create the foundation of a chronological list of Jerry Jones’ Top 10 Failures.

1. In 1965, at age 25, he had a chance to buy the San Diego Chargers for $5.8 million.

2. In 1989, Jones bought the Cowboys, fired Tom Landry and hired Jimmy Johnson – and announced all three blockbusters in a quickly-assembled introductory press conference.

“It was my biggest Cowboys mistake because I didn’t allow each of their stories their full due,’’ Jones told me. “There wasn’t time for Cowboys fans to really deal with each of the changes. I wish I had a do-over on that.’’

3. In 1989, the Cowboys selected QB Steve Walsh in the Supplemental Draft. Not a bad idea on paper, and as it turned out, a year later Johnson engineered a deal that sent Walsh (his old U of Miami quarterback) to New Orleans for a blockbuster package that included a first-, second- and third-round pick.

But locker-room chemistry isn’t played on paper. Walsh’s presence created a year’s worth of tension for quarterback Troy Aikman, who’d been the No. 1 overall player taken in the regular 1989 Draft. The “competition,’’ if one could call it that, was a problem. The draft picks eventually acquired salvaged a near-disaster.

4. In 1993, The Cowboys were coming off of a Super Bowl win and unsigned Emmitt Smith was asking for “quarterback money.’’ Jones played hardball as the defending champs started 0-2. Jones’ stance was losing him favor in the locker room (especially when Charles Haley threw his helmet through a Texas Stadium wall). … so he relented.

5. Jones quickly have a four-year deal worth over $13.5 million to Smith, who went on to be a central piece in two more titles, became the NFL’s all-time leading rusher and earn induction into the Hall of Fame.

The person selected by Emmitt to presented him into the Hall? Jerry Jones.

6. In 1994, flush off two Super Bowl wins but tiring of the disloyalty of Johnson, Jerry tipsily insisted to reporters that “any one of 500 coaches could have won those Super Bowls.’’ The Jimmy/Jerry insults flew – and eventually, Johnson flew the coop. This wasn’t all Jones’ fault. But had either man swallowed some pride, the 90’s Cowboys might have been even more dynastic.

7. In 1998, Randy Moss was available with the eighth overall pick. Dallas owned the pick and Moss – a magnificent college player the Cowboys personnel department was guaranteeing would be a magnificent pro – stated his desire to become a Cowboy.

Problem: Right at that time, the team was dealing with a PR nightmare due to Michael Irvin’s behavioral and legal problems. Moss, too, was plagued by some of the same problems. Thinking way too linearly, fans and media screamed that a team employing one troublesome wide receiver couldn’t possibly take on another troublesome wide receiver.

Jerry listened, and selected solid defensive end Greg Ellis rather than Hall-of-Fame candidate Moss.

8. In 2000, the Cowboys traded two first-round picks to Seattle for wide receiver Joey Galloway. The concept: A bright, shiny toy to extend the career of Aikman. In his first game for the Cowboys, Galloway tore his ACL and missed the rest of the season, and the remainder of his Dallas career was lackluster.

This deal is especially notable because it occurred in February – just two months ahead of the NFL Draft, when Dallas could’ve used the first of those picks to select its own, young, affordable star receiver.

9. In 2008, Jones reached for another bright, shiny toy. Dallas gave up first-, third- and sixth-round picks to Detroit for receiver Roy Williams. Williams never quite proved to be a difference-maker, and yet the Cowboys multiplied their error by later signing him to a $54-million extension.

10. In 2011, Ratliff had two years left on his contract when the Cowboys signed him to the extension. He was a four-time Pro Bowler but was also 30 years old at the time – arguably at the crossroads of when a long-term commitment to a player becomes unwise.

Worth noting: Dallas isn’t done paying the piper on these sorts of commitments. Jones hopes he doesn’t someday have to add the contracts given DeMarcus Ware and Miles Austin to his “legal pad.’’ But for now, these “bottom 10’’ will have to suffice.

(©2013 CBS Local Media, a division of CBS Radio Inc. All Rights Reserved. This material may not be published, broadcast, rewritten, or redistributed.)

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