2) How Good Is Good Enough For Garrett?

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(Football season is finally approaching. After a long offseason, the Cowboys are set to depart for training camp on July 25. During this final month before they begin practice in Oxnard, Calif., the staff of DallasCowboys.com is going to preview the 20 biggest questions facing the Cowboys heading into 2019.)

FRISCO, Texas – With most of last year’s playoff roster back, the Cowboys’ top training camp storyline might be the list of Pro Bowlers seeking long-term deals.

There’s also head coach Jason Garrett entering the final year of his current contract.

All offseason Cowboys owner/general manager Jerry Jones has reiterated his support for Garrett, who has guided the team to three NFC East titles in the last five years.

“I do my best work without a net. I really do,” Jones said at the NFL combine in March. “I'm better with a little risk involved. In essence, there's a little bit of no net here. … He (Garrett) is not in danger of having any issue with his credibility with his players or anybody else. It's well known, the support I have for him.”

Garrett has always deflected questions about his contract, focusing fully on his role each day as head coach. But his contract is sure to remain a hot topic with the Cowboys pushing to build on last year’s divisional-round playoff appearance.

What will it take for Garrett to secure an extension? That’s the next installment in our 20 Questions series.

Mickey Spagnola: That’s a convoluted question. Good enough for what? To appease Cowboys owner Jerry Jones, who has his head coach working on the final year of his contract? Or to appease the fans, who likely will think “win a Super Bowl or else?” Jerry hasn’t said definitively. But here is what the Cowboys are trying to do this season, the ninth under Jason Garrett’s jurisdiction. Come up with four consecutive winning seasons, something they haven’t done since five straight winning seasons from 2005-09. Come up with five winning seasons over a six-year period, there best string of success since those six winning seasons over seven years from 2003-09. Qualify for the playoffs in back to back seasons, something they have not done since 2006-07. Qualify for the playoffs for the third time in five years, something they haven’t done since three times in four years from 2006-09. Become the first NFC East team to repeat as division champs since the Eagles won four straight from 2001-04, along with becoming the first NFC East team to win four division titles in a six-year span since the Eagles won five in six years (2001-06). That “good enough?” Sustaining success over a lengthy period of time? Sure, the ultimate goal is to win a Super Bowl, or at least qualify for the NFC title game, something the Cowboys have come up one-game short of doing so in three of the past five years. If any or all of that is not “good enough,” then the Cowboys would be setting up no margin of error for the next head coach.

Nick Eatman: This question reminds of trying to figure out the next Ring of Honor inductee. We can debate it all we want, but it comes down to what Jerry Jones thinks – and really no one else. Personally, I think Garrett just needs to show improvement from 2018. And there’s two real ways to do that – have a better record than 10-6 and/or get past the Divisional Round. Now if the Cowboys were to get to 12-4 but lose the first playoff game, that might be problematic for Garrett. If the Cowboys were to sneak into the playoffs at 9-7 but get to the Championship game, that might help him. I just think there needs to be some kind of improvement from last year, which isn’t easy because they finished strong. But at some point, the Cowboys have to take the next step. So it’s got to be the NFC Championship Game or a monster-like regular season. To be safe, Garrett probably needs both.

Bryan Broaddus: Over these past several years I have called for the removal of Jason Garrett as the club’s head coach. Fortunately for Garrett the front office has not listened to me. Garrett is clearly at the crossroads of his tenure. Despite winning 73 games during the regular season it’s the lack of overall success in the post season which point Garrett in this situation. Throughout the history of this franchise how head coaches performed in the playoffs is the standard that has been set. Jerry Jones has been more than patient with Garrett and it’s time for him to reward Jones’ loyalty and deliver success in the playoffs. I am not talking about just winning a wild-card game but finding a way of putting this roster in a NFC championship game with a chance to go to the Super Bowl. Could I be asking too much – maybe? The schedule is not easy but barring injury this is one of the most talented rosters in the league. Jason Garrett knows he needs to deliver because anything else in my opinion will not be good enough.

Rob Phillips: To Nick’s point, I don’t think anyone really knows the answer to this question except Jerry and Stephen Jones. I know they have a lot of faith in Garrett. As Jerry said at the combine, “Hopefully that can come together, we get him a Super Bowl and he'll be maybe the longest-tenured coach in the history of the Cowboys.” The Super Bowl is the goal, especially with the youth and talent on this roster. But anyone who’s won the title will tell you it takes a lot of luck, too, especially good fortune on the injury front. Injuries (Tony Romo in 2015) and suspensions (Ezekiel Elliott in 2017) hindered their chances to repeat as division champs. As we sit here in July, no one knows what the 2019 record will be, or the circumstances around the result. But Garrett has earned a long-term extension before, and I think it’s entirely possible he gets one again if the Joneses believe this young team is continuing to ascend on his watch.

Lindsay Draper: It makes me chuckle knowing that by the end of this season, we’ll have the answer to this question. Jason Garrett is in the last year of his contract, so time will certainly tell what the true bar is set at for this team. No two rosters are ever the same from year to year, but for the most part, this team is coming back similar to its 2018 look, which is strong. This group just needs to get within a championship reach – back to the playoffs – and see where the chips fall.

David Helman: From the time the 2018 season ended, the talk around the Cowboys has been about “taking the next step.” Well, for this team, the next step is the NFC Championship Game – if not further. Obviously, there are so many twists and turns to an NFL season, there’s no way to predict the challenges Jason Garrett might have to overcome in 2019. But sitting here in mid-summer, this looks like one of the most talented teams in the NFC, so taking the next step is certainly plausible. Now, do I honestly think it’s this black and white? Not really. If the Cowboys lose in the divisional round of the playoffs again, I have a hard time believing Jerry and Stephen Jones wouldn’t extend his contract. It sounds so bizarre to let a guy walk after making three playoff appearances in four years. But I also know that if I were Jason Garrett, I wouldn’t want to chance it. In order to keep his job 100 percent safe, he needs to make the playoffs – and he should probably make some noise once he gets there.

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