Caldara was elected to the board of directors for the
Regional Transportation District, and eventually became its chairman. In 1998, he replaced
Tom Tancredo as president of the
Independence Institute, a Colorado think tank. Colorado Attorney General
John Suthers investigated Caldara for voting fraud, but chose not to prosecute him. Suthers called the incident "suspicious," and said that it was questionable that Caldara ever intended to become an
El Paso County resident. Suthers noted "arguable ambiguity” in the same-day voter law, and took no action. In January 2014, Caldara said, "I told you what I did was legal, neener-neener-neener." From 2016 through 2020, Caldara wrote a weekly column for
The Denver Post. In January 2020, Jon Caldara was dismissed by the Denver Post, for what he felt were his politically incorrect statements on
transgender rights, which had been reflected repeatedly in the media, and his voicing his concerns the ensuring of inclusivity comes at the price of sacrificing the right to
free speech. This view was contradicted by the Denver Post’s editor on January 17, 2020. On February 1, 2020, it became public that Caldara had been employed as a columnist by
The Gazette. In March 2020, Caldara called on
Colorado Governor Jared Polis for the suspension or reversal of the ban on single-use plastic or paper bags, as these, compared to reusable, and more emissions-intensive, bags produced in
China, would lower the public health risk possibly without any adverse environmental effect. ==Personal life==