From 1973 to 1974, Middlebrooks was in private practice in Orlando, and was an assistant general counsel, governmental assistant, and general counsel for GovernorReubin Askew from 1974 to 1977. He returned to private practice for the next twenty years in West Palm Beach, Florida.
Electronic Frontier Foundation vs. Shipping & Transit (2016): Middlebrooks dismissed the case against patent troll Martin Kelly Jones (Case No.:16-CV-80855-MIDDLEBROOKS/BRANNON).[3]
Donald J. Trump v. Hillary R. Clinton, et.al (2022): Middlebrooks dismissed the suit brought by Donald Trump against Hillary Clinton, the Democratic National Committee, and 26 others, seeking damages for alleged conduct surrounding the 2016 presidential election.[4] Middlebrooks concluded that "most of Plaintiff’s claims are not only unsupported by any legal authority but plainly foreclosed by binding precedent as set forth by the Supreme Court and the Eleventh Circuit." and that Trump "is not attempting to seek redress for any legal harm; instead, he is seeking to flaunt a two-hundred-page political manifesto outlining his grievances against those that have opposed him, and this Court is not the appropriate forum."[5][4] Two months after he dismissed the case, Middlebrooks assessed Trump's lawyers $50,000 in penalties, plus $16,000 to cover the legal fees paid by one of the defendants.[6] In a later ruling, he imposed additional sanctions of $937,989.39 on Trump and his lead law firm in the litigation for bringing a lawsuit “in bad faith for an improper purpose” that “needlessly harmed” the defendants, “in order to dishonestly advance a political narrative.”[7]
