With the Jacksonville Jaguars 2018 season going the way it did, most thought general manager Dave Caldwell would be fired after the season for sure, but team owner Shad Khan ultimately decided to keep him around. That without a doubt means the Jags will need to improve significantly in 2019 for him to keep his job. When looking at the state of the roster that’s doable, but won’t be easy as the Jags have a lot of work to do, especially offensively.
Here are the four toughest decisions Caldwell will have to make in 2019:
When to release Blake Bortles

The first big task for Caldwell will be to decide when is the right time to cut his most important draft pick in quarterback Blake Bortles. Of course, being that he deemed Bortles the team’s franchise quarterback in 2014, it will be the most difficult decision of his career as general manager, but simply put, it’s time to progress forward as Bortles has been sporadic throughout his five-year tenure.
Per CBS Sports cap expert Joel Corry, Bortles will be due a $1 million roster bonus on March 17, which is basically when Caldwell will have to decide whether he wants to release Bortles, which will be a $16.5 million dead cap charge, or wait for a post-June release, which would drop the hit to $11.5 million. However, by waiting, the Jags’ available cap savings from the release wouldn’t be added until June, when free agency and the draft will be over. A post-June release would also push some of his dead money off ($5 million) to 2020.
Some fans believe the Jags should just rip the band-aid off in 2019 by cutting him before June, while others are fine with distributing the blow. That said, if the Jags don’t plan to do much in free agency, a post-June 1 release may be the way to go although the money they would save wouldn’t reflect until then. However, handing out big-time free agent contracts is part of the reason the team is in their current predicament, so maybe taking a chill approach this free agency period is the smart thing to do because the class isn’t that strong to begin with.
Make a decision on how the team will acquire a new starting quarterback

After the decision on Bortles, the Jags will need to find an option to replace him, which could come through a trade, free agency or the draft. Of course, the veteran player who has been the most heavily associated with the Jags is former Philadelphia Eagles quarterback Nick Foles, who elected to exercise his contract option and become a free agent. It’s now up to the Eagles to decide if they want to franchise then trade him, which would put his price tag at $25 million on the season.
Most tend to think the Eagles are bluffing, but if they aren’t, CBS Sports’ Pete Prisco stated that it’s highly unlikely the Jags would trade picks for Foles, and that statement probably has some validity to it. Ultimately, the Jags would be giving up a top-3 pick, taking on Foles’ high price tag and would have to come to a long-term deal with him, which is simply absurd. However, if he’s a free agent there certainly could be interest, but with limited cap space and the money they have tied into Bortles, fans have to wonder if the Jags could afford Foles when looking at what Kirk Cousins got on the open market. Additionally, Foles is a player who could struggle outside of coach Doug Pederson’s system.
With Foles’ chances to be a Jag looking gloomy, the team could still look to free agency to sign a cheap veteran and players like Tyrod Taylor, Teddy Bridgewater or Ryan Tannehill may be some smart affordable options. If Caldwell goes that route, it would almost certainly mean they would also look to the early rounds of the draft for a quarterback, which would give them an answer for the future while the veteran serves as a short-term answer for 2019.
Personally, I think Dwayne Haskins or Kyler Murray would be the way to go alongside the veteran as both won’t take long to coach up, however, Haskins will almost certainly require the Jags to trade up. He’s a solid prospect though and would be well worth it after missing out on Bortles.
Make a decision on what high-priced veterans they should move on from to shave some cap space

With the Jags being $4.3 million in the hole, Caldwell will need to get them back in the positive and give them some breathing room on top of that. The moves they have planned for Bortles and defensive tackle Malik Jackson could put them at approximately $10-15 million depending on if the Jags cut Bortles before June, or after.
Defensive lineman Calais Campbell recently revealed he’s working on a restructured deal which should help, while the Jags may look to do the same for Marcell Dareus. After that, if needed, they could cut players like tight end Austin Seferian-Jenkins, running back Carlos Hyde, safety Tashaun Gipson and right tackle Jermey Parnell among notables. Personally, I feel most of those names are expendable aside from Gipson, which would free up approximately $14 million.
Decide on what offensive needs to address in the draft alongside QB

If the Jags decide to trade up for Dwayne Haskins (which would be smart) they’ll almost have to give up one to two early picks in this year’s draft. That would leave them with one to two more of their top-4 picks. It would then fall on Caldwell to decide which of the Jags’ many pressing needs to address early come April. Outside of the quarterback position, they have needs at tight end, receiver, right tackle, right guard and maybe even at running back.
Needless to say, everything won’t be addressed in one offseason, however, prioritizing their needs is a big task in itself. That said, with the tight end and wide receiver classes being strong in the second to third round range, maybe those would be the positions he’d lean towards in the draft as players like Irv Smith Jr., David Sills, Kevin Harmon and more could be available Day 2 options.