Before he became a US district judge, Winsor was a judge in Florida's First District Court of Appeal from 2016-2019. He was Florida's solicitor general and worked in private practice before that.
He graduated from Auburn University in 1997 and got his law degree from the University of Florida in 2002.Winsor previously dismissed a lawsuit challenging the 'Don't Say Gay' bill In February 2023, Winsor issued a 21-page ruling dismissing a lawsuit challenging Florida's Parental Rights in Education Act, whichWinsor particularly took issue that the plaintiffs in the suit — who were parents, students, and teachers — didn't allege harm or seek monetary damage, he"Plaintiffs have shown a strident disagreement with the new law, and they have alleged facts to show its very existence causes them deep hurt and disappointment," Winsor wrote.
He went through several examples where the plaintiffs said they were deprived of free speech or discriminated against because of the law, and cited specific details contending they weren't, legally speaking. "It does not matter that removing a library book, changing curriculum, or denying access to extracurricular activities could constitute a cognizable injury," Winsor wrote."What matters is whether Plaintiffs have alleged that they themselves suffered a cognizable injury traceable to the Provision's enforcement and redressable by an injunction against it. They have not."