[2] His work has frequently been cited in judicial opinions, including in Supreme Court cases pertaining to the First and Second Amendments.

He holds a Bachelor of Science in foreign service from Edmund A. Walsh School of Foreign Service, a Juris Doctor from New York University School of Law, and a master's degree in political science from UCLA, where he studied under Karen Orren.

[4] Winkler practiced with Howard Weitzman and represented Michael Jackson in his defense against charges of sexual assault.

[12] Winkler has written extensively on legal history topics, such as the origins of campaign finance law,[13] the women's suffrage movement,[14] and the regulation of political parties.

[16][17][18] Along with historian Leonard Levy and UCLA School of Law professor Kenneth Karst, Winkler edited the six-volume Encyclopedia of the American Constitution.