In 1845, President James K. Polk sent Wickliffe on a secret mission to report on British and French intents with regard to annexing Texas and to assess the feasibility of the United States undertaking such an action.

In 1863, he again sought the office of governor, but federal military forces interfered with the election, resulting in a landslide victory for Thomas E. Bramlette.

[3] Wickliffe attained his early education at the local schools of Springfield, then attended Wilson's Academy in Bardstown.

[2] For a year, he received private instruction from James Blythe, acting president of Transylvania University, then read law with Martin D. Hardin, a cousin on his mother's side.

His friends considered his gambling excessive, and two of them – Duval and Judge John Pope Oldham – devised a scheme to break Wickliffe of his habit.

The two knew that Wickliffe would be collecting several thousand dollars at the upcoming session of the Bullitt County court.

The Wickliffes contracted with John Rogers, architect of St. Joseph's Cathedral in Bardstown, to construct their residence, which they dubbed "Wickland".

[2] He first served as an aide-de-camp to General Joseph Winlock, and on August 24, 1813, he enlisted as a private in Martin H. Wickliffe's company.

[11] On September 2, 1813, he was chosen as aide-de-camp to General Samuel Caldwell and served in this capacity at the October 5, 1813, Battle of the Thames.

[10] Historian Robert Powell opined that Wickliffe's break from party loyalty may explain his lack of committee appointments in his early years in the House.

[10] In 1830, Wickliffe was chosen by his colleagues as one of the managers of the impeachment trial proceedings against Missouri District Court judge James H.

[15] He was elected lieutenant governor of Kentucky in 1836, defeating Democrat Elijah Hise by a margin of just over 1,300 votes.

[1] He advocated raising property taxes to offset spending deficits that had climbed to $42,000 by 1839, but the legislature borrowed money to meet the current expenses instead.

[1] The only areas where he called for more spending were improvements in river navigation, preservation of state archives, and public education.

[1] Wickliffe campaigned on behalf of the Whig ticket of William Henry Harrison and John Tyler in the presidential election of 1840.

[6] On August 1, 1844, Wickliffe and two of his daughters boarded the steamship Georgia traveling from Old Point Comfort in Virginia to Baltimore, Maryland.

[8] Wickliffe supported the annexation of Texas, an issue that helped seal Clay's defeat in the 1844 presidential canvass.

[20] Stockton and Wickliffe believed that if they could provoke a Texan invasion of Mexico, the United States would have a stronger case for annexing Texas.

[1] On February 18, 1841, the Kentucky General Assembly elected James Turner Morehead to the U.S. Senate; Wickliffe received twenty votes in this contest.

[6] He opposed the idea of secession, and was a member of both the 1861 Peace Conference and the Border States Convention that attempted to stave off the Civil War.

[2] In April 1861, he attended a secret meeting at the Capitol Hotel in Frankfort where participants planned to arm Union supporters in key areas of the state.

[24] After Braxton Bragg's forces destroyed the railroad trestles near Bardstown, Wickliffe personally hired Joseph Z. Aud to carry the area's mail by private carriage.

[4] Military authorities considered him subversive, however, and interfered with the election; Wickliffe lost to Thomas E. Bramlette in a landslide.

[1][22] Wickliffe served as a delegate to the 1864 Democratic National Convention in Chicago, casting his vote for George B.