Cannon was a long-time foe of Andrew Jackson, and spent much of his political career opposing Jacksonite policies.
[1][2] Cannon received a common school education and tried several occupations as a young man, working as a saddler, merchant and surveyor, and undertaking the study of law, before eventually becoming a planter in Williamson County.
[4] Cannon entered political office in 1811, representing Williamson, Rutherford, Maury, Bedford, Lincoln, and Giles counties in the state senate in the 9th Tennessee General Assembly (1811–1812).
[1][7][8] Cannon first sought the Tennessee governorship in 1827 in a field that initially included Sam Houston, former governor Willie Blount, Felix Grundy, and aging frontiersman John Rhea.
Cannon's election was also aided by division among Tennessee Democrat-Republicans over the U.S. Presidential candidacy of Tennessean Hugh Lawson White in opposition to the national party's choice of Martin Van Buren.
[1][14] Cannon was publicly criticized for his implementation of the new laws, especially in East Tennessee, where voters grew impatient over his lack of support for the Hiwassee Railroad.
[1][13] In 1839, state Democrats, determined to defeat Cannon, convinced rising politician and Speaker of the U.S. House of Representatives James K. Polk to run against him.
Cannon typically delivered slower, more methodical arguments, and was outshone in the debates by the quicker and wittier Polk.
[8][14] The earliest of these interactions involved a horse track known as Clover Bottom that Jackson owned together with a pair of brothers, William and Patten Anderson.
[15] Cannon is purported to have lost substantial amounts of money and other possessions from gambling at Clover Bottom, and is said to have blamed Jackson and the Andersons for his losses, suspecting them of fixing races.
[8][14] The second encounter occurred in 1812 when Cannon served on a jury in a trial of Jonathan Magness who, with his two sons David and Perry Green, had been accused of murder in the death of Patten Anderson.