Jackson has been quoted as saying his two biggest regrets from serving as president is not shooting Henry Clay and not having Calhoun hanged.
My question is, with such disdain for Calhoun, why did Jackson choose him as his running mate in the 1828 election? Did Jackson actually like/trust Calhoun at one point and then see the nullification crisis as a betrayal?
Briefly, the break that began with Calhoun and Jackson occurred over the Petticoat affair, in which John Eaton married Peggy O'Neale shortly after her husbands death. It was seen as extremely scandalous for a women to remarry so soon, as social moors dictated that a widow should remain single for a significant amount of time to properly morn.
Now, Calhoun's wife Floride lead all the prominent women of Washington to snub John and Peggy, angering Jackson (Jackson was sympathetic to the Eatons as his first wife was also subjected to scandal and ridicule). Ironically, John C. Calhoun had little interest or opinion in the affair, but did nothing to reign in his wife actions.
Calhoun was also moving towards the politics of a sectional radical, which didn't help his cause down the line either.