Caldwell was the Republican nominee for Florida Commissioner of Agriculture in 2018, but lost the general election to Democrat Nikki Fried.

Matt was a member of the Florida House of Representatives from 2010 to 2018, serving on and chairing several committees during his tenure, including tax policy, redistricting, insurance and banking, agriculture, natural resources and public lands, transportation and infrastructure, local, federal, and military affairs, & oversight of government operations, such as pensions & elections.

[1] When incumbent State Representative Nick Thompson opted to run for a position as a Circuit Judge on the 20th Judicial Circuit of Florida in 2010 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.

[2] In Caldwell's last race for the Florida House in 2016, he won 51% to Democratic candidate John W. Scotts 38% and Independent Matt Millers 10.6%.

In the Republican primary election, Caldwell won the party's nomination receiving 34% of the vote to Denise Grimsley's 26%, Mike McCalister's 12%, and Baxter Troutman's 26%.

[2] In 2020 Caldwell ran for Lee County Property Appraiser after Ken Wilkinson retired from his 40 year long tenure.