He was appointed commander of the 101st Airborne Division in 2019[2] and succeeded by Major General Joseph P. McGee in 2021.

Later, he would serve as a company commander of the 3rd Infantry Division until 1998, where he started his Master studies at LSU.

For two years, from 2009 to 2011, Winski served as the 4th Brigade combat team commander of the 1st Cavalry Division based at Fort Hood in Killeen, Texas.

He would attend the Army War College afterwards for a year from a Washington Institute for Near East Policy fellowship.

Between serving as a legislative liaison and the Chief Army legislative liaison, he was the deputy commanding general for operations for the 82nd Airborne Division based in Fort Bragg, North Carolina, for two years between 2014 and 2016, serving as a brigadier general then.