And as Caldwell delivered the good news to Dante Fowler Jr., the Florida edge rusher who in another two minutes would become the first non-quarterback off the draft board Thursday night, he couldn't resist having a little bit of fun at the audaciously attired young man's expense.
You know, just for kicks.
"I tell you what, I think those shoes put you over the top tonight," Caldwell told Fowler, referring to the gold, spiky footwear the defensive end had paired with a gaudy white suit for his star turn at Chicago's Auditorium Theatre.
"Oh yeah!" Fowler replied.
After pausing for effect, Caldwell continued, "Alright, man. Well, feel free to leave 'em in Chicago."
Caldwell smiled. Fowler laughed. So did the three dozen scouts, coaches and other Jags officials in a draft room that would soon be filled with hearty applause. While the Tampa Bay Buccaneers and Tennessee Titans weighed trade offers before selecting quarterbacks Jameis Winston and Marcus Mariota, respectively, with the first two overall selections, the Jags summarily dismissed the scant deal-down scenarios at their disposal and landed the top player on their draft board.
Unlike last year, when Caldwell masterfully concealed his intentions before surprisingly snagging quarterback Blake Bortles with the third overall selection, there wasn't a huge sizzle factor accompanying the Fowler pick. Yet for a regime that has won just seven games in two seasons, but is brimming with optimism heading into the 2015 campaign, it was another reason to celebrate the dawn of a new era.
"We're getting better -- we truly believe that," owner Shad Khan said from the back of the war room, about 30 minutes after Fowler's selection. "And this is another step. We believe this guy can be a gamechanger, and as far as our specific needs, he fits us to a tee.
"It worked out nicely from a business perspective, too. We've been fortunate the last two years -- Blake went to Central Florida, so that generated excitement, and Dante's a Florida guy. It's not (Tim) Tebow, but it's the next best thing."
So yes, things are looking up in the northernmost part of the Sunshine State, a term that could also serve as an apt description of the owner's current mindset. Conversely, when Khan purchased the Jaguars in January of 2012, the team's downtrodden condition extended far beyond the playing field.
"People weren't buying tickets, and we weren't attracting sponsors," Khan recalled. "When I was a young man, I had a summer job going door-to-door in Elgin, Ill., selling vacuum cleaners. Put it this way: Selling vacuum cleaners was easier than selling Jaguars tickets when we arrived."
The turnaround on the business side has been striking -- in a typically shrewd move, Khan brokered a deal for sponsorship of the war room, with fantasy-sports site Fan Duel paying for the naming rights.
The shift in football fortunes has yet to materialize, meaning that Caldwell and coach Gus Bradley -- each hired following the 2012 campaign -- is under pressure to perform in Year 3.
"There's no number of victories (they have to reach to save their jobs)," Khan said. "We have to show that we're moving in the right direction. They know they need to make a jump this year. And I don't need to tell them that. I think we will."
To Khan, Caldwell and Bradley, drafting Fowler was a significant move toward that end. While tempted to select USC defensive tackle Leonard Williams or Alabama receiver Amari Cooper -- and, to a lesser extent, West Virginia receiver Kevin White or Clemson defensive end Vic Beasley -- the trio locked in on Fowler, reasoning that he could make the biggest impact.
Jacksonville's most accomplished edge rusher, Chris Clemons, turns 34 in October, and Bradley -- who previously coached Clemons as the Seahawks' defensive coordinator -- recalled a conversation with his former boss, Seattle coach Pete Carroll, after a 30-28 divisional-round playoff defeat to the Atlanta Falcons in January 2012.
"Chris Clemons hurt his knee in that game, and we had to put an outside linebacker (Mike Morgan) at edge rusher, and we really struggled," Bradley said. "On the flight back from Atlanta, Pete said, 'I'll never do that to you again ... that position is too important.' You remember after that he signed (Cliff) Avril and (Michael) Bennett and (O'Brien) Schofield -- he just brought in waves of guys, one after the other. That's what we'd like to build here."
Almost immediately after the Fowler selection was announced, Bradley got a text from Carroll: "Awesome pick, Gus!" Caldwell received similar messages from colleagues around the league, one of whom texted, "You just got the best player in the draft."
There were high-fives aplenty, but though the Jags were off the clock, the intrigue wasn't over. Having been willing to move back as far as the seventh or eighth selection for the right price, Caldwell had been underwhelmed by the lack of interest from teams immediately below him; now, with the 36th overall selection as bait, he was suddenly in move-up mode. There were a few players he regarded as special who, if they'd fallen into the 20s, might have compelled him to try to get back into the first round.
However, those players (who he preferred to remain nameless until after the draft's conclusion) went off the board in short order, and at 9:48 p.m. he announced in the war room, "I guess we can wrap it up (for the night); we'll be keeping our picks."
The mood in the room remained sunny well past midnight, as Caldwell prepared to head home. With the fourth pick in the second round, and more than four players -- at multiple positions -- who are relatively high on the team's draft board, the GM believes the Jags are well positioned to get another impact performer on Friday.
"We'll get a good player, however it shakes out," Caldwell said, acknowledging that trading down a few spots in the second and/or third rounds remained a possibility. "We're still a work in progress, but we're making strides."
And if some of those strides happen to be made by a young man wearing gold, spiky shoes?
Well, when the dude in question is a potential gamechanger, Caldwell, Bradley and Khan will gladly roll with it.