Background
Caldwell was born in Gainesville and attended Florida Gulf Coast University, from which he received a degree in history in 2004, and he began working as a real estate appraiser.
Caldwell was born in Gainesville and attended Florida Gulf Coast University, from which he received a degree in history in 2004, and he began working as a real estate appraiser.
In 2008, when Democratic State Senator Dave Aronberg ran for re-election in the 27th District, which sprawled from West Palm Beach to Cape Coral and included parts of Charlotte County, Glades County, Lee County, and Palm Beach County, Caldwell ran against him. During the course of the campaign, an elections complaint was filed against Caldwell over the fact that he sent out two different mailers paid for from his campaign treasury, despite the fact that he did not report enough money to cover th charges of the mailers. When incumbent State Representative Nick Thompson opted to run for a position as a Circuit Judge on the 20th Judicial Circuit of Florida rather than seek re-election, Caldwell ran to succeed him in the 73rd District, based in northern Lee County, including Fort Myers and stretching from Suncoast Estates to Gateway.
He faced Jason Moon, John Schultz, and Deanna Casalino in the Republican primary, where he was attacked for taking campaign contributions from the United States. Sugar Corporation.
During the campaign, Caldwell campaigned on improving the region"s economy by "bringing back freight rail service" so that the industrial base of the region can grow. "We"ve got freight rail lines running through the county, but they are very under-utilized.
The fact is that there are other areas of the state that have been very successful with this and as a result have a lower unemployment rate." Despite the fact that the Marco Island Sun Times endorsed Peacock, they praised Caldwell for having a "valuable" perspective and a respectable "record of local service." In the end, Caldwell defeated both of his opponents, winning 59% of the vote to Peacock"s 38% and Rodriguez"s 3%. When state legislative districts were redrawn in 2012, Caldwell was moved into the 79th District, which retained most of the territory that he had previously represented in the 73rd District.
In the Republican primary, he was opposed by Jon Larsen Shudlick, whom he was able to defeat in a landslide, winning renomination with 86% of the vote.