Winna winna, chicken dinna!
Chrysler apprenticed in the railroad shops at Ellis, Kansas, as a machinist and railroad mechanic. He then spent a period of years roaming the west, working for various railroads as a roundhouse mechanic with a reputation of being good at valve-setting jobs. Some of his moves were due to restlessness and a too-quick temper, but his roaming was also a way to become more well-rounded in his railroading knowledge. He worked his way up through positions such as foreman, superintendent, division master mechanic, and general master mechanic.
From 1905-1906, Chrysler worked for the Fort Worth and Denver Railway in Childress, a West Texas city considered the "Gateway to the Texas Panhandle." He later lived and worked in Oelwein, Iowa, where there is a small park dedicated to him.
The pinnacle of his railroading career came at Pittsburgh, where he became works manager of the Allegheny locomotive erecting shops of the American Locomotive Company (ALCO).
