A five-year pro, Caldwell (10-1) has never shied away from the fast route, and believes he would have won a Bellator title already had the company never moved away from its tournament format.
That said, the former collegiate wrestler admits he only became a complete, well-rounded mixed martial artist within the past year -- and the timing could not be better for his first title shot at Bellator 184 this week in Thackerville, Oklahoma.
"When I signed with Bellator in 2014, I really I had a chance to get into the tournament, beat everyone and win the belt," Caldwell told ESPN. "But things changed and went in a different direction. Even my career went in a different direction. I started fighting at 145 pounds and moved to 135 because I knew it would be a quicker route to the title.
"Two, three years later I'm getting my shot and it could not have come at a better time."
A former NCAA national wrestling champion at NC State, Caldwell isn't just looking to win his first MMA championship on Friday. He wants to set the stage for bigger things to come, on bigger platforms than a Friday night event in Oklahoma.
Since former Strikeforce CEO Scott Coker took over Bellator in mid-2014, the promotion has seen a significant change in "tent pole" events, in markets such as Houston, San Jose, Los Angeles and New York. So far, Caldwell, originally from New Jersey, has appeared on smaller shows, mostly in the Midwest.
Caldwell says he's not complaining about that, but he expects the promotion to switch gears on him after it sees what he's capable of on Friday.
"I enjoy the fans in Thackerville and it's a great atmosphere, but of course I want to fight in New York, L.A., New Jersey," Caldwell said.
"I love Bellator and what they've done with me, but I don't think there's been a 135-pounder in this promotion who brings everything to the table. I think I'm the first guy to do it. Nobody wants to watch [previous champion] Joe Warren or Eduardo Dantas. But when it's my time to be champion, I'm looking forward to defending my title on a big card."
The makeup of the 135-pound division was part of the reason Caldwell opted to drop in weight.
Dantas (20-4), of Brazil, has been exceptionally successful at a young age, but Caldwell has always seen a favorable matchup in him.
"They don't bring any swag to the organization," Caldwell said. "Everybody hates Joe. Dantas is not a bad guy, but he doesn't bring anything that catches your attention. I figured we'd fight a couple times eventually and I never felt threatened by him. Stylistically, he's just another guy that doesn't match up well with me.
"He's still a kid and I'm the teacher. I'm taking him to school on October 6."
The confident Caldwell has suffered just one loss so far in his career, a stunning submission defeat to Joe Taimanglo in July 2016. Shortly after the loss, Caldwell switched camps in favor of a move to Alliance MMA in San Diego, where he trains alongside the best bantamweight of all time, former UFC champion Dominick Cruz.
"Our sparring sessions are gruesome, hard and not fun to go through," Caldwell said. "It's a good feeling to know I can compete with the best in the world. I feel I'm a full, well-rounded mixed martial artist and I think that will definitely show on Friday."