Whakaotihia te rerenga e whai ake nei: I muri i tana mahi hei kaiwhakahaere mara mo te Michigan Democratic Party i te pōtitanga perehitini o te tau 2000, kātahi i runga i te kaupapa a John Kerry mo te perehitini i te tau 2004, ka uru atu a Simon ki te kaupapa a Barack Obama
Ko ia te kaiwhakahaere o te kaupapa ā-peresideni i te tau 2008, e noho ana i te tari matua o Chicago. Hei wāhanga o tēnei pakanga, i whakahaerehia e ia ngā pūranga raraunga mō te whanonga pōti me ngā manakohanga. Ko tana rautaki o te whaainga tika i whakawhiwhia ki te awhina ki te tautuhi i nga kaitono kaore i whakatau i taea e Obama te whakahoahoa. Whai muri i te pakanga, i tohua ia i te tau 2009 ki te mahi i roto i te Whakahaere Obama i te Tari Hauora me nga Ratonga Tangata, i reira i arotahi ai ia ki te whakahou hauora me te Medicare.