Jonathan Windy Boy was born on August 28, 1958, in Fort Belknap, Montana, and was raised in Box Elder, Montana. He is a member of the Democratic Party. Windy Boy is divorced and has two children. Outside of his legislative work, he is a business owner and has worked in oil field exploration. He is known as a traditional Grass Dancer and has worked as a drug and alcohol prevention speaker. His professional experience includes serving as a guest columnist for Indian Country Today. He has been a member of the Tribal Council of the Chippewa Cree Tribe since 1999 and served as the Tribe's Vice-chairman from 2008 to 2010. He also serves as a full-time THPO for the Chippewa-Cree Tribe of Rocky Boy.

In 2019, Windy Boy stepped down from legislative duties after being found guilty of sexual misconduct. The misconduct stemmed from inappropriate texts he sent to female colleagues between mid-August and October 2017. Allegations and anecdotes also began circulating regarding a history of sexual misconduct on the reservation. Despite this, he ran for re-election as Representative of District 32 and served in the 2021 legislative session.

Education

Windy Boy attended Northern Montana University. In 1980, he earned an associate degree in telecommunications from the Southwest Indian Polytechnical Institute.

Political Experience

Jonathan Windy Boy currently serves as a member of the Montana State Senate, representing District 16. He assumed this office on January 6, 2025, and his current term is scheduled to end on January 3, 2029. He succeeded Mike Fox in this position.

His previous legislative service includes:
* Montana House of Representatives: Represented District 32 from January 2, 2017, to January 6, 2025. He succeeded Bruce Meyers and was succeeded by Mike Fox.
* Montana State Senate: Served from January 5, 2009, to January 2, 2017. He was preceded and succeeded by Frank Smith.
* Montana House of Representatives: Represented District 92 from January 6, 2003, to January 5, 2009.

Throughout his tenure, Windy Boy has been assigned to numerous committees. During the 2025-2026 session, he serves on the Education and Cultural Resources Committee, the Finance and Claims Committee, and