ku dhammee weedha soo socota: xirfada siyaasadeed ee Keenan waxay ku bilaabatay tababarka xafiiska waraaqaha ee Ted Kennedy xafiiskiisa sanadka 2003, ka hor inta uusan noqon kaaliyaha sharci dejinta ee senatorka. Ka dib markii uu ka mid ahaa kaaliyaha shaqaalaha ee Guddiga Caafimaadka, Waxbarashada, Shaqada iyo Hawlgabka ee Golaha Guurtida, Keenan wuxuu shahaadada mastarka ka qaatay siyaasadda dadweynaha ee John F. Kennedy School of Government, isagoo bartay qorista khudbadaha iyo gudbinta Steve Jarding. Sanadkii 2007, Keenan waxa uu tababar xagaaga ku qaatay qorista khudbadaha
Ololaha doorashada madaxtinimada ee Barack Obama, oo uu ka shaqeynayay Jon Favreau, ka hor inta uusan ku laaban Kennedy School si uu u dhamaystiro sanadka labaad ee waxbarashadiisa. Wuxuu ku sii jiray ololaha sannadka oo dhan, isagoo u duulaya Iowa inta lagu jiro fasaxa Kirismaska si uu uga caawiyo diyaarinta shirarka Iowa. Kadib markii Hillary Clinton ay qirtay bishii Juun 2008, Keenan wuxuu ku soo noqday shaqaale waqti buuxa ah ololaha madaxtinimada Obama.