HOUSTON, TX - DECEMBER 28: Team general manager David Caldwell (L) chats with Shahid Khan, the owner of the Jacksonville Jaguars on the field before their game against the Houston Texans at NRG Stadium on December 28, 2014 in Houston, Texas. (Photo by Scott Halleran/Getty Images)

Will this be the season that gives Jacksonville Jaguars general manager David Caldwell more security or will it be his undoing with the organization?

With just one winning season after seven years on the job, Jacksonville Jaguars General Manager David Caldwell is much more than just ‘on the hot seat’ heading into a season full of uncertainty. The 2020 NFL Draft will not only be a defining moment for Caldwell, but will make or break not just his future with this franchise… but very possibly, his career as an NFL GM.

Heading into the 2020 NFL Season, there’s quite a bit of certainty for everyone in the National Football League — coaches, players, owners, front offices, agents, and the like, due to the worldwide COVID-19 pandemic that is giving citizens across the universe a ‘new normal’.

Not to be taken lightly, this pandemic has even made it’s way in NFL circles, infecting even the healthiest of individuals who are in the best shape of their life leaving no one person immune.

NFL star @VonMiller of the Denver @Broncos opens up about his diagnosis with coronavirus. He became the second known case among NFL players. “It all started with a simple cough,” he says. pic.twitter.com/QW7pkR7mFj — 3rd Hour of TODAY (@3rdHourTODAY) April 17, 2020

For the first time in the history of the NFL Draft, it will be a completely virtual event that features a melting pot of analysts from both ESPN and the NFL Network. Instead of the Jacksonville Jaguars brass sitting together in the war room, watching every possible angle of coverage, each member will instead be at home, adhering to the CDC’s guidelines for Social Distancing.

Each team’s IT Department has been hastily working to ensure each person has the necessary resources so that the draft continues as much as normal as can possibly happen. Caldwell’s set-up is as vast and expansive with technology as they get.

At GM Dave Caldwell’s house in Ponte Vedra Beach: 1 laptop, 3 @surface tablets, 2 65-inch TV monitors, 1 projector screen, 3 external speakerphones (2 mobile, 1 hard line), 2 @Bose headsets, 1 iPad, 1 light kit, 1 UPS for all essential equipment, 1 backup generator. pic.twitter.com/bECtfs9xaL — Tad Dickman (@TDickman89) April 22, 2020

History is being made every single day across the entire world right now. But on Thursday evening, as the first round of the 2020 NFL Draft commences, Caldwell will at the start of, in my opinion, the defining moment of his own history. One can only not do their job for so long with mediocre results before having to join the 22 million others filing for unemployment in systems that keep crashing resulting in long lines of masked citizens bracing pandemic conditions hoping to still get a paycheck.

In seven seasons on the job, Caldwell has only produced one in which the Jacksonville Jaguars reached the postseason, back in 2017 when the team lost the AFC Championship Game to the New England Patriots. Some might admit they were calling for Caldwell’s head well before then. Others may say that since then, he’s done nothing to deserve to stick around.

Sure, you could argue that old school Tom Coughlin came back through the doors and created all kinds of ruckus. Sure, you could argue that there have been some other outside factors beyond Caldwell’s control and yes, the NFLPA didn’t do him any favors when advising free agents to think twice when considering whether or not to sign with the Jacksonville Jaguars.

That said, there’s still a consequence for performing poorly, at least, in the real world we all live in unless your Shad Khan and completely incapable of firing a subordinate who isn’t doing their job to an acceptable standard.

Then again, maybe 38 wins and 90 losses is acceptable to Khan who… unless he makes big changes to the current power structure of this regime, for lack of a better term, is lazy. If you ask me, I just think Khan doesn’t want to do what needed to happen a long time ago in firing Caldwell.

He didn’t do it when he decided to make Coughlin the football czar in Jacksonville when he brought him in, nor did he when he let Coughlin go shortly before the end of the 2019 season, a time that saw Khan leave Caldwell and Jacksonville Jaguars Head Coach Doug Marrone in place but reporting directly to Khan himself.

At rate #Jaguars are jettisoning players or on the verge of doing it, u have to wonder if owner Shad Khan is open to idea of letting Doug Marrone and Dave Caldwell finish the last 2 years on contracts even if they go 6-10 or worse in 2020. I’m sure fan base will be fine with that — Eugene Frenette (@GeneFrenette) March 3, 2020

I can tell you one thing, if the Jacksonville Jaguars don’t win at least eight games in 2020, Marrone WILL be fired and looking for work. The same should happen to Caldwell and my gut tells me there would be enough of an uproar from fans and media alike to force Khan’s hand — despite his laziness when it comes to Caldwell and doing right by the franchise.

Even with possession of the top pick in the 2021 NFL Draft and the speculation behind closed doors that the Jacksonville Jaguars are indeed ‘Trevor Lawrence’s team’, I certainly think this year’s draft is more important.

We’ve talked about how the Jags, others might build capital towards ’21, with Clemson QB Trevor Lawrence graduating in December, entering that draft. Which sounds great. Here’s the thing: You’re gonna have to be the worst team in the NFL. Whoever gets that pick ain’t trading it. — Albert Breer (@AlbertBreer) April 21, 2020

To be clear, I don’t think knocking the 2020 NFL Draft ‘out of the park’ will be completely enough to single-handedly save Caldwell’s job at the end of next season, but I do think it will make or break his career. The day that Khan does fire Caldwell, in my opinion when you look at his entire body of work over his tenure in Jacksonville, will be the last day Caldwell possess the title of NFL GM.