Nyorai kupfuurira kweiyi ndima - Muna January 2008, McCaskill akatsigira ipapo-Senator Barack Obama mumushandirapamwe wake
nokuda kwekusarudzwa kweDemocratic kuti ave purezidhendi, achimuita mumwe waSenator vokutanga kuita kudaro. Akanga ari mumwe wezviso zvaioneka zvikuru mukushandira kwake, uye kutsigirwa kwake kwakanga kwakakosha kukunda kwaObama kwakakomba mumasarudzo ekutanga eMissouri munaFebruary 2008. Akati mwanasikana wake Maddie ndiye akamunyengetedza kuti atsigire pachena Obama. Aiwanzotaurwa nezvake somunhu aigona kuzova mutevedzeri wemutungamiri wenyika waObama, asi haana kumbobvira afungwa nezvazvo. Akataura pazuva rokutanga reDemocratic National Convention muna August 2008.