Jay was seen as an extremely controversial choice to be George Washington's minister to Great Britain. He was seen as too pro-British and therefore Washington appointed Monroe, a francophile, as minister to France as a counterbalance. Jay was sent to Britain with the authority to negotiate trade treaties with the country–information that never was conveyed to Monroe. Therefore, Monroe took much heat in Paris when word arrived of Jay's Treaty, which granted substantial trading rights to Britain.
Thomas Jefferson sent Monroe to help Livingston negotiate the purchase of New Orleans from France in 1803. Livingston remained forever bitter about Monroe receiving most of the credit for the Louisiana Purchase.
John Quincy Adams
Adams, the son of former President John Adams, served as Monroe's secretary of state and later succeeded Monroe in the presidency in 1825.