Not re-signing Dak Prescott would go down as one of the “most infuriating moments” in Cowboys history

It’s just a matter of time before we’ll have all the answers regarding the second contract of one Dakota Prescott. How much? How long? And of course, one of utmost importance - with whom?

The first two questions are what many of us await as the last one seems inevitable. Surely, the front office is not going to let Dak get away, right? We all agree? Prescott chances of remaining with the Cowboys seem pretty high, but what if that actually didn’t happen? Just entertaining the idea of that is not pleasant. What would be the Cowboys contingency plan?

Could you imagine having all these offensive weapons with a talented offensive line (when healthy) only to witness issues at the quarterback position that completely squandered those skills. Cowboys fans should know first hand about how such a thing can completely derail the season. In 2015, Dallas was 3-1 in games when Tony Romo started, only to go 1-11 in games started by the rolodex of backups: Brandon Weeden, Matt Cassel, and Kellen Moore.

Sure, the organization may be able to find a more viable option than those guys as Andy Dalton showed he was a solid backup this past season, but solid won’t cut it. They Cowboys aren’t equipped enough defensively to just be okay on offense. They need to be great. They need Dak.

If Jerry and Stephen Jones pull a fast one on us and decide that Dak is really NOT their quarterback, then it could go down as one of the worst moves this front office has made in their 61-year storied history. How would it compare to other infuriating front office moves this team has made? Let’s take a stroll down memory lane and get our blood boiling because that’s always fun to do.

Joey Galloway trade

The Roy Williams trade stands out a little more because it’s more recent, but older fans will recall the time Jerry gave up not one, but two first-round picks to acquire Galloway from the Seattle Seahawks back in 2000. This was one of several moments Jones’ general-managing philosophy took on that “one player away” mentality. The Cowboys had just lost Michael Irvin to retirement the season before and the hour glass was dwindling on Troy Aikman’s playing career. The front office acted in haste and not only gave up heavy draft capital to get him, but also signed him to a pricy seven-year contract extension.

It certainly didn’t help matters that Galloway suffered a season-ending ACL injury during his Cowboys debut. He would return healthy the following year, and although he did okay, he wasn’t the same star caliber 1,000+ yard receiver he was in Seattle. If you think fans had apprehensions about giving up a first-round pick for the 24-year-old Amari Cooper, just imagine how they would’ve reacted giving up two firsts for the 29-year-old Galloway. What was Jerry thinking?

The TO escapade

The TO experience was a roller coaster ride as emotions went up and down as more and more things happened. To start with, Owens was known around the league as a prima donna, locker-room cancer as he already had burned bridges with his first two teams, San Francisco and Philadelphia. Not only that, but the hatred grew heavy for Cowboys fans after his midfield star incident while playing against the Cowboys. So, when Jerry brought him to Dallas to wear the star, it’s safe to say, he wasn’t welcomed with open arms.

Owens started to earn some forgiveness with what he did on the field. Whether he was catching passes from Drew Bledsoe or Romo, TO injected life into the offense and suddenly the Cowboys were relevant again. He only spent three years in Dallas, but in each season he had over 1,000 yards receiving and double-digit touchdowns. And while he still was his colorful self with his celebration antics, he never got into any trouble off the field. And when fans got a behind the scenes look at the team from HBO’s Hard Knocks, you could see how incredibly disciplined he was in taking care of his body. From an effort and results perspective, it was actually a little unjust to not love us some TO.

Of course, like it did everywhere else, the marriage between TO and the team he played for dissolved. During his last year in Dallas, the Cowboys lost three of their last four games, causing them to miss the playoffs. Romo was especially bad in those three games, turning the ball over nine times, two of which actually resulted in defensive touchdowns. TO voiced his frustrations with the idea that Romo was forcing the ball to his BFF Jason Witten, and many fans who had a front row seat to those games might say he had a legit gripe. In the end, TO was made the scapegoat, and the Cowboys released him.

Whether it was signing him or cutting him, it just felt like the front office didn’t have their head on straight in dealing with that whole situation.

Out with Jimmy, in with Barry

We all should know by now that Jerry Jones alone wasn’t the blame for Jimmy Johnson leaving the Cowboys back in 1994. Johnson has gone on record many times saying he was looking for an out as he never was a guy who could stay in one place very long. And while a long tenure of the Johnson era was never going to happen, you had to believe it could’ve lasted a little bit longer if Jerry Jones would’ve just kept his mouth shut.

After hitting rock bottom in 1989, which led to the firing of Tom Landry (another angry fan moment by the way), the Cowboys turned things around rather quickly. In fact, too quickly. It’s hard not to think that Jones thought this whole Super Bowl winning football gig wasn’t all that hard, especially after he decided to get drunk one night and share his thoughts with sportswriters. The Cowboys dynasty ended in hotel bar when Jones told reporters that “500 coaches could have won a Super Bowl with that team” as he collectively patted himself on the back for assembling great talent while downplaying the achievements of his head coach.

Shortly thereafter, it was decided that Johnson was no longer the head coach of the Cowboys, and Jones got his wish to do things his way as he replaced Johnson with the hands-off/contribute-absolutely-nothing-to-the-team Barry Switzer. While the residual talent of Johnson’s team did net the Cowboys a third Super Bowl in four years, the franchise went into a tail spin that has been very difficult to get out of. Jerry learned that hard way that he needs other great people around him to experience success, and it’s something he’s struggled with for over two decades.

What was your most infuriating front office moment, and where would letting Prescott leave in free agency rank on your list?