[7][4] Grinstead became a well-known local businessman and was approached to run for Mayor of Louisville in 1897, which he declined.
[1][4] After learning that his backer—Republican Party boss Charles Sapp—had used some questionable tactics to get votes for Grinstead, he declined the nomination,[1] earning the nickname "Honest Jim".
[4] He became the first Republican mayor of Louisville to be elected by general voters when he became mayor in 1907[5] to complete the term started by Paul C. Barth,[7] whose 1905 election had been thrown out by the Kentucky Court of Appeals.
[4] Grinstead was elected county commissioner in 1917 and served until his death in 1921.
[4] He was buried in Cave Hill Cemetery,[8][4] which Grinstead Drive runs alongside.