Though that type of money could warrant an all-out spending spree, it's going to be important for the top brass in Jacksonville to vet out each free-agent target and stay away from the pseudo candidates.
The first step Caldwell has to take in order to clear up some of the uncertainty surrounding this year's class of free agents is figuring out what players make the most sense for this roster.
Whether you're judging it from a performance standpoint or a financial one, if the Jaguars are going to spend money in free agency, they have to make sure each player they pursue can be a long-term solution.
Using a series of advanced metrics and film study to determine which players would help this roster improve, it's time to set the odds and check out six free-agent targets the Jaguars will go after this offseason.
All stats and free agency info provided by NFL.com unless noted.
All advanced stats courtesy of Pro Football Focus (subscription required) unless noted otherwise.
Odds: 90 percent
Out of all the in-house names set to hit free agency, Jaguars quarterback Chad Henne is the one guy who deserves to be back next season.
Although Henne will never be a franchise-caliber signal-caller, what makes him valuable is the experience he has with offensive coordinator Jedd Fisch's scheme and the veteran leadership he brings to the table.
Expressing his desire to see Henne return to Jacksonville, Ryan O'Halloran of The Florida Times-Union (subscription required) reported that Caldwell "still plans to reach out" to Henne's agent before free agency officially gets underway.
While he was a bit closemouthed about the situation, Vito Stellino of The Florida Times-Union declared that signing Henne to a new deal is a "major priority" for this franchise.
At the end of the day, sitting down and fleshing out a new contract makes a lot of sense, not only for the Jaguars, but also the 28-year-old QB—talking to O'Halloran (subscription required), Henne expressed his desire to return to Jacksonville next season.
If the two sides can come to an agreement, Jaguars fans would graciously welcome the former University of Michigan QB back with open arms.
Odds: 65 percent
If you take the whole franchise quarterback part out of the equation, Jacksonville's biggest need this offseason comes down to adding as many top-flight pass-rushers as they possibly can.
After finishing the last two seasons registering the fewest sacks in the National Football League, Caldwell needs to do whatever he can to somehow find a way to redress the issues that have hampered this defensive line.
Scanning the market for potential free-agent targets, Cincinnati Bengals defensive end Michael Johnson is one player who would make a world of difference for the Jaguars.
Using Pro Football Focus' formula as a barometer to judge Johnson's ability, the former Georgia Tech Yellow Jacket has established himself as one of the elite pass-rushers in the NFL.
Registering 40 quarterback hurries and 16 QB hits, the 6'7" Johnson finished the 2013 season as PFF's fourth-ranked 4-3 defensive end.
A prime candidate to enjoy a substantial payday, NFL Media Insider Ian Rapoport tweeted that Johnson is one player who will "definitely" hit the open market.
Talking to Jessica Blaylock and Ryan O'Halloran on 1010 XL/92.5 FM, Coach Bradley mentioned that the Jaguars would considering adding bodies to bolster their pass rush.
If that theory holds true, signing a perennial edge-rusher like Johnson seems like the perfect remedy to alleviate some of the defensive woes this team has experienced.
Odds: 60 percent
Looking to shore up the Jaguars offensive line, Caldwell's excellent adventure through free agency will lead him right to the doorsteps of Cleveland Browns center Alex Mack.
Mack's production over the course of his career in Cleveland should pave the way for his bank account to enjoy a bountiful chunk of cabbage this offseason.
Despite the influx of cap room the Jaguars have at their disposal, making a play for Mack this offseason will come down to how comfortable Caldwell is unloading long-term money.
While frugal spending isn't necessarily a bad thing, Mack is one player who deserves a bloated contract.
Going by PFF's standards, Mack has graded out as a top 10 center every season since 2009. On top of that, the five-year veteran has yet to miss a game over the course of his career.
Understanding that he's worth his weight in gold, Mack's chances of hitting free agency are still up in the air.
While NFL Media Insider Ian Rapoport reported that "bad feelings built up" with the prior regime could lead to his exodus from Cleveland, Rapoport also mentioned, now that former general manager Mike Lombardi and CEO Joe Banner are gone, there's still a chance Mack finds his way back to the Browns.
Luring him away from Cleveland will be a pivotal decision Caldwell has to commit to this offseason. If he can find a way to convince the All-Pro center that Jacksonville is the right fit, Mack would be a first-rate addition who would help guide this offensive line into the future.
Odds: 60 percent
While he may not have the pedigree that Mack does, Kansas City Chiefs offensive guard Geoff Schwartz is another player Caldwell should keep an eye on this offseason.
After signing a one-year deal with the Chiefs during the 2013 offseason, the 27-year-old enjoyed immense success under first-year head coach Andy Reid. According to PFF, Schwartz finished his 2013 campaign as the eighth-best guard in the NFL.
When you watch him on film, the best part about Schwartz's game has to be his versatility. Playing right guard, left guard and even right tackle at one point last season, Schwartz established himself as one of the league's premier "swing" offensive linemen.
Examining all of the holes on Jacksonville's offensive line, the biggest need seems to be at the left guard position.
Harrowing play by Will Rackley—PFF's 79th-ranked guard—led Caldwell to express his concerns with Ryan O'Halloran of The Florida Times-Union (subscription required) over how the team will use the three-year guard out of Lehigh University next season.
At it's core, developing a solid foundation of players who can work hard and win the war in the trenches is a great blueprint for building a successful NFL franchise.
That's why for Caldwell, signing a guy like Schwartz would be an efficient way to help solidify this offensive line without hemorrhaging a ton of cap space in the process.
Odds: 55 percent
Houston Texans running back Ben Tate has all of the intangibles needed to a franchise running back in today's NFL.
Although he mainly served as a change-of-pace option for Arian Foster, Tate demonstrated he is more than capable of handling a full workload when he was out there on the field.
Averaging 4.7 yards per carry over his tenure in a Texans uniform, Tate's impressive vision and overall stellar football acumen helped Houston establish one of the league's most spirited running attacks.
With each passing day, the odds of Tate returning to Houston seem to diminish a little bit more.
Talking with John McClain of the Houston Chronicle (h/t Ultimate Texans Blog) about his future, Tate said there is a good chance he "probably” wouldn't wind up playing for the Texans next season.
Caldwell's quest to rebuild the Jaguars ground game could very well start with pursuing Tate's services in free agency.
With Ryan O'Halloran of The Florida Times-Union (subscription required) reporting that Jaguars owner Shad Khan "supported Caldwell’s decision" to let Maurice Jones-Drew hit the open market, the need for a proficient running back has to become a top priority this offseason.
Though going through the draft is always a nice way to accrue talent, inking the 25-year-old tailback to a long-term deal would help bring a sense of stability to Fisch's offensive scheme.
Odds: 35 percent
Heading back over to the defensive side of the ball, Caldwell has to go out and find an adept defensive player in free agency who won't break the bank. That player's name? Pittsburgh Steelers linebacker Jason Worilds.
At just 25 years old, Worilds was one of the most effective 3-4 outside linebackers in the NFL last season. Playing 792 snaps, according to PFF's count, Worilds' production ranked in the same ballpark as prominent edge-rushers like Terrell Suggs, Lamarr Woodley and John Abraham.
Even though most of his experience has come from playing in Dick LeBeau's disruptive 3-4 scheme, Worilds' athleticism and ability to rush the passer makes him too valuable to overlook.
As Thomas Beekers of FieldGulls.com meticulously described in his piece on Bradley's tenure as the Seattle Seahawks defensive coordinator, the defensive scheme he built featured a lot of rotating personnel and hybrid fronts.
If Bradley and current Jaguars defensive coordinator Bob Babich want to infuse that same mantra in Jacksonville, adding an explosive edge-rusher like Worilds would be a great start.
Even though Worilds expressed interest in returning to Pittsburgh next season during an interview with ESPN.com (h/t Scott Brown), the former Virginia Tech star has earned himself the right to see what his value would be on the open market.