In February 2018, Winkler announced his intentions to run for the legislative office he previously held in District 46A.[3] He was re-elected, succeeding Peggy Flanagan, who had left the house to run for lieutenant governor.
DFL legislators elected Winkler to serve as Majority Leader in November 2018, and he took office in January 2019.
Winkler announced that he will retire from the Minnesota House of Representatives at the end of his 2021–2023 term. He went on to run in the DFL primary election for Hennepin County Attorney on August 9, 2022, finishing in 3rd place.[4]
He was first elected in 2006, and was re-elected in 2008, 2010, 2012, and 2014.
In 2021, legalizing recreational marijuana came up for a vote in front of the Minnesota House of Representatives for the first time. Winkler was a lead proponent of the push.[5]
On May 21, 2015, Winkler announced he would resign effective July 1, 2015. His wife at the time, Jenny, accepted a job as an executive with the Rezidor Hotel Group, which is headquartered in Brussels, Belgium, and his family moved there to support her.[11]
Comments on Voting Rights Act lawsuit
Following the United States Supreme Court's decision in Shelby County v. Holder, Winkler took to Twitter to write, "VRA majority is four accomplices to race discrimination and one Uncle Thomas" referring to Justice Clarence Thomas, an African American. "Uncle Tom" is a derogatory used against blacks who are perceived as being apologetic for their race. Winkler later deleted the tweet and posted, "Deleted Tweet causing offense regarding Justice Thomas. I apologize for it, but believe VRA decision does abet racism."[12] On Twitter, he added that he did not understand "Uncle Tom" as a racist term.[13]