Kammala wannan jumla: Keenan ya fara aikin siyasa ne a matsayin mai ba da horo a ofishin ofishin majalisar dattijai na Ted Kennedy a shekara ta 2003, kafin ya zama mataimakin majalisar dattijai. Bayan wani ɗan lokaci a matsayin mataimakin ma'aikaci na Kwamitin Lafiya na Majalisar Dattawa, Ilimi, Aiki da fansho, Keenan ya sami digiri na biyu a fannin manufofin jama'a a Makarantar Gwamnati ta John F. Kennedy, yana nazarin rubutun magana da isarwa a ƙarƙashin Steve Jarding. A shekara ta 2007, Keenan ya ɗauki aikin bazara a cikin rubutun magana a kan
Gasar zaben shugaban kasa ta Barack Obama, yana aiki a karkashin Jon Favreau, kafin ya koma Makarantar Kennedy don kammala shekara ta biyu na karatunsa. Ya ci gaba da shiga cikin yakin neman zabe a cikin shekara, ya tashi zuwa Iowa a lokacin hutun Kirsimeti don taimakawa wajen shirya shirye-shiryen Iowa. Bayan da Hillary Clinton ta yarda a watan Yunin 2008, Keenan ya dawo a matsayin cikakken ma'aikaci a yakin neman zaben shugaban kasa na Obama.