In 1974 Pritzker joined the US Army as a private and rose through sergeant to 2nd lieutenant, with 11 years service in the US and West Germany. This was followed by 16 years in the Illinois National Guard. After retirement in 2001, Pritzker was given the honorary rank of Colonel.
In Pritzker founded the Tawani Foundation "to enhance the awareness and understanding of the importance of the Citizen Soldier" and the Pritzker Military Library. In 2003 the Tawani Foundation made a $1.35 million donation to the University of California's Palm Center to study the feasibility of transgender people serving in the military and police and fire departments.
In 2013 Pritzker announced a legal name change to Jennifer, and that she was starting transition. Thus she became the first trans billionaire. Forbes magazine lists her at #327 in its rich list, and estimates that she is 'worth' $1.7 billion.
++In January 2016, Pritzker donated $2 million for a Chair in transgender studies at the University of Victoria, BC, with Aaron Devor to be the inaugural chair.
- "Jennifer Natalya Pritzker, Decorated Colonel And Hyatt Hotel Heir, Announces Identity As A Woman". Huffington Post, 08/23/2013. Online.
- George Chidi. "Chicago billionaire comes out as transgender, backs study of transgender military service with cash". The Raw Story, August 23, 2013. Online.
- Alexandria Fisher. "Evanston Billionaire James Pritzker Changes Name to Jennifer Pritzker". NBCChicago, Aug 25, 2013. Online.
- "Jennifer Pritzker Becomes First Transgender Billionaire". Forbes, 9/16/2013. Online.
- Dawn Rhodes. "Jennifer Pritzker's foundation donates $2 million for transgender studies". Chicago Tribune, Jan 10, 2016. Online.
- Rose Kaplan. "Jennifer Pritzker’s Foundation Gives $2 Million for Transgender Studies at Canadian University". Tablet, January 2016. Online.
- Jennifer N Pritzker. "Why should I support a political party that is marginalizing me out of existence?". The Washington Post, January 8, 2019. Online.