Windham Jr. plays basketball for leisure and attributes his passion for politics in large part to his late great-grandmother, Rose Simon.

[2] On August 7, 2018 Windham Jr. won the four-way Democratic primary for Missouri House of Representatives in District 85 to succeed Clem Smith with 43.7% of the vote.

[4] As an incoming legislator, Windham was elected vice-chair of the Missouri House Democratic Caucus for the 100th General Assembly.

In his legislative duties Windham has focused on increasing access to higher education, criminal justice reform, and community revitalization.

[3] Rep. Windham has proposed several progressive bills including HB 910 (2021) which would repeal state sales taxes on groceries while implementing an estate tax, HB1354 (2021) which would create the Missouri Office of Racial Equity, and HB 884 (2021) which would make Missouri's A+ Scholarship a first-dollar scholarship.