He attended Kenyon College, where he received a bachelor's degree in history and later, an honorary doctorate of laws.

[3][4] Following his years at the Mount Vernon News, Winkler worked as a New York-based reporter and assistant editor at The Bond Buyer.

[9] Under Winkler, the organization won the 2015 Pulitzer for Explanatory Reporting with Zachary Mider’s "painstaking, clear and entertaining explanation of how so many U.S. corporations dodge taxes and why lawmakers and regulators have a hard time stopping them.

[18] And in 2014, the Los Angeles Press Club recognized Winkler and Michael Bloomberg with the President's Award for Impact on Media.

[19][20] Winkler serves on the board of directors of the International Women's Media Foundation (IWMF),[21] the Committee to Protect Journalists (CPJ),[22] the International Center for Journalists (ICFJ),[23] and Bloomberg L.P.[24] He also serves on the board of trustees for both Kenyon College[25] and the Kenyon Review.