Rubuta ci gaba don wannan sakin layi - Guild ya shiga siyasa a 1881, yana aiki a matsayin memba na Massachusetts House of Representatives. Ya zama memba na kwamitin Jam'iyyar Republican na jihar a 1894 kuma ya zama sananne a ƙasa lokacin da ya zama mataimakin shugaban majalisa na Republican na 1896. A shekara ta 1900 ya yi aiki a kan yakin neman mataimakin shugaban kasa na Roosevelt, kuma ya yi tafiya tare da Roosevelt bayan kisan gillar Shugaba William McKinley
ya daukaka Roosevelt zuwa shugabancin kasa.