[1] At age 18, he began to study law in the office of attorney Henry L. Palmer, while teaching school in the winters to bring in money.

In 1858, he was hired as a clerk in the law offices of Abbott, Gregory, and Pinney, in Madison, Wisconsin, where he completed his legal studies.

[3] While studying the law, Winkler became a fervent abolitionist and campaigned extensively for Abraham Lincoln in the 1860 United States presidential election.

[1] Immediately after the outbreak of the war, his law partner entered the Union Army cavalry and left the entire business in Winkler's hands.

As the urgency of the war ramped up in 1862, Winkler chose to shut down the business entirely and began organizing a company of volunteers for a new regiment.

Winkler resigned from the staff of General Schurz to return to his regiment and assist in leading it through the remaining days of the Battle of Gettysburg.

Their colonel briefly rejoined the regiment, but he was forced to depart due to his lingering wounds in November 1863, leaving Winkler in command.

[4] That Winter, Winkler briefly resumed his judge advocate duties to represent General Schurz in an inquiry over his performance at the Battle of Wauhatchie.

Schurz believed he had been slandered by General Hooker's account of the battle, and appointed Winkler to represent his interests in a court of inquiry.

His nomination for brigadier general was submitted by President Andrew Johnson on January 13, 1866, and was confirmed by the United States Senate on March 12, 1866.

[5] His younger brother, August Gotlieb Winkler, moved to Greenville, Alabama, where he was a prosperous merchant and served on the city council.