Montana Politics if Brian Schweitzer won in 2000 against Conrad Burns.

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I think he very well could be 2004 Democratic presidential or VP nominee, 2008 VP nominee and 2016 presidential or VP nominee.
So, Schweitzer:
- win reelection in landslide in 2006
- reelected in landslide in 2012
- Presidential (wins)/VP nominee (loses) in 2016
- if he were VP nominee and ticket lost an election, he would have run again in 2018 and then run for Governor in 2020 and win

So, assuming now 2027

Brian Schweitzer
U.S. Senator from Montana
Term in office: January 3, 2001 - December 31, 2020

(run for Governor, win and appoint former Governor Bullock to his seat after his inauguration)

Governor of Montana
Term in office: January 7, 2021 - incumbent

OR

U.S. Senator from Montana
Term in office: January 3, 2001 - November 15, 2016
President of the United States of America
Term in office: January 20, 2017 - January 20, 2025

Assuming scenario 1 happened:

Jon Tester
Governor of Montana
Term in office: January 3, 2005 - January 7, 2013
U.S. Senator from Montana
Term in office: January 3, 2015 - incumbent

(reelected 2020, 2026 and will be reelected again many times)

Steve Bullock
Attorney General of Montana
Term in office: January 3, 2009 - January 7, 2013
Governor of Montana
Term in office: January 7, 2013 - January 7, 2021
U.S. Senator from Montana
Term in office: January 7, 2021 - incumbent

(elected in 2022 special, reelected in 2024 and will be reelected again many times)