In 2008, he was elected to the Oregon House of Representatives for District 42, representing inner Southeast and Northeast Portland.
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In 2013, Bailey angered some environmentalists by voting in favor of the Columbia River Crossing mega highway project, which will 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 OLCV event shortly after the vote in the Oregon House.
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In 2008, Bailey earned a plurality victory over three other candidates for the Democratic nomination for House District 42 for the seat vacated by Diane Rosenbaum, who was running for election to the Oregon Senate, and then defeated Pacific Green Party candidate Chris Extine by a wide margin to win election to the seat.
Jules Verne | Jules Massenet | Bill Bailey | Ringling Bros. and Barnum & Bailey Circus | Pearl Bailey | Kay Bailey Hutchison | Derek Bailey (guitarist) | Derek Bailey | Old Bailey | Jules Dassin | Rumpole of the Bailey | Étienne-Jules Marey | David Bailey | Jules Maigret | Bailey | Danny John-Jules | F. Lee Bailey | David Bailey (photographer) | Jules Shear | Jules Michelet | Jules Ferry | Jules Dumont d'Urville | Jules Chéret | Jules Bastien-Lepage | Corinne Bailey Rae | Bailey Road | Richard W. Bailey | Pierre-Jules Hetzel | Jules Perrot | Jules Olitski |