In 2013, Bailey angered some environmentalists by voting in favor of the Columbia River Crossing mega highway project, which was projected to increase greenhouse gas emissions 32% in the area by 2030 if built; he was presented with the mock environmental "Cars Rejuvenating Carbon" award during an Oregon League of Conservation Voters event shortly after the vote in the Oregon House.

He sponsored bills to increase state funding for biking and walking facilities[18][19] and to allow an Idaho stop for cyclists.

[24] He succeeded Liesl Wendt, who had been appointed to fill the seat on an interim basis when Deborah Kafoury resigned to run for County Chair.

[31] Bailey voluntarily limited campaign contributions to $250, while Wheeler did not and was criticized for taking money from out of town sources.

[33] In September 2020, Bailey filed an elections complaint against Portland mayoral candidate Sarah Iannarone alleging that she misled voters about her educational credentials.

[34][35] In January 2017, he joined the Oregon Beverage Recycling Cooperative as chief stewardship officer,[36] and served as CEO in 2023.