Lincoln appointed two individuals from the border states to his cabinet. Montgomery Blair of Maryland, who was popular among anti-slavery and border state Democrats, became Lincoln's first Postmaster-General. Blair came from a prominent political family, as his father, Francis Preston Blair, had served as an adviser to President Andrew Jackson, while his younger brother, Francis Preston Blair Jr., was a major Unionist leader in Missouri. Blair's Postal Service aptly responded to the challenges posed by the Civil War, but the Blair family alienated key Northern and border state leaders during the war. Seeing Blair as a political liability, Lincoln dismissed Blair from the cabinet in September 1864, replacing him with William Dennison. Missouri provided the other border state cabinet member in the form of Attorney General Edward Bates. Bates resigned in 1864, and was replaced by James Speed, the older brother of Lincoln's close friend, Joshua Fry Speed.