[1] Olander played in the minor leagues from 1981 to 1994 with the Phillies, Milwaukee Brewers, and Houston Astros organizations.

[1] However his following seasons were shortened by injury and he eventually left the Phillies organization and signed as a free agent with the Astros who soon after traded him to the Brewers.

Olander was expected to fight for a spot on the Brewers 1992 40-man roster but he broke his leg in early May.

In October 2007, the Detroit Tigers promoted Olander from national crosschecker to big league scout, a job he still holds.

[6] He was responsible for recommending Cody Ross to the Tigers prior to the 1999 Major League Baseball Draft.