Shortly after graduating from law school, he was commissioned as the only major in the 11th Kentucky Cavalry, serving under Confederate Brigadier General John Hunt Morgan during the American Civil War.

At their 1875 nominating convention, state Democrats chose McCreary as their nominee for governor, and he won an easy victory over Republican John Marshall Harlan.

[5] He obtained his early education in the region's common schools, then matriculated to Centre College in Danville, Kentucky, where he earned a bachelor's degree in 1857.

[7] In 1859, he earned a Bachelor of Laws from Cumberland and was valedictorian of his class of forty-seven students; he was admitted to the bar and commenced practice at Richmond.

Colonel Chenault was killed as the Confederates tried to capture the Green River Bridge at the July 4, 1863, Battle of Tebbs Bend.

Approximately two hundred men, commanded by McCreary, mounted a charge and escaped their captors, but they were surrounded the next day and surrendered.

[13] Moreover, newly elected governor Preston Leslie had opposed a bill granting Cincinnati Southern's request when he was in the state Senate in 1869.

[8] In 1875, McCreary was one of four men, all former Confederate soldiers, who sought the Democratic gubernatorial nomination—the others being John Stuart Williams, J. Stoddard Johnson, and George B.

[17] In joint debates across the state, McCreary stressed what many Kentuckians felt were abuses of power by Republican President Ulysses S. Grant during the Reconstruction Era.

[17] Despite a late infusion of cash and stump speakers in favor of his opponent, McCreary won the general election by a vote of 130,026 to 94,236.

[19] In his first address to the General Assembly, McCreary focused on economic issues to the near exclusion of providing any leadership or direction in the area of government reforms.

[21] The proposed legislation drew the ire of bankers and capitalists; it was also widely panned in the press, notably by Louisville Courier-Journal editor Henry Watterson.

[21] The issue of improving navigation along the Kentucky River was raised numerous times by Representative James Blue during the 1876 legislative session.

Despite Blue's promises of manifold benefits to the state from such an investment, parsimonious legislators defeated a bill allocating funds for the improvements.

After more than a week of caucusing among Democratic legislators, the nominations of McCreary, Knott, and Lindsay were withdrawn, and Williams was elected over Boyd.

[27] McCreary bested both men, and in the general election in November, defeated Republican James Sebastian by a margin of 2,146 votes.

An advocate of free silver, he was appointed by President Benjamin Harrison to be a delegate to the International Monetary Conference held in Brussels, Belgium, in 1892.

As chairman of the House Committee on Foreign Affairs, he authored a bill to establish a court that would settle disputed land claims stemming from the Gadsden Purchase and the Treaty of Guadalupe-Hidalgo.

[34] His opponent, incumbent William J. Deboe, had been elected as a compromise candidate six years earlier, becoming Kentucky's first-ever Republican senator.

[35] In a largely undistinguished term as a senator, he continued to advocate the free coinage of silver and tried to advance the state's agricultural interests.

Beckham countered by citing his strong stand in favor of Prohibition, as opposed to McCreary's more moderate position, and by touting his support of a primary election instead of a nominating convention, which he said gave the voters a choice in who would represent them in the Senate.

Ultimately, Beckham prevailed in the primary by an 11,000-vote margin, rendering McCreary a lame duck with two years still left in his term.

Both supported progressive reforms such as the direct election of senators, a non-partisan judiciary, and the creation of a public utilities commission.

[39] O'Rear claimed that Democrats should have already enacted the reforms their party platform advocated, but his only ready line of attack against McCreary himself was that he would be a pawn of Beckham and his allies.

[39] Caleb Powers, convicted three times of being an accessory to Goebel's murder, had been pardoned by Republican governor Augustus Willson and had recently been elected to Congress.

His son's daughter, Harriet Newberry McCreary, served as the mansion's first official hostess during her summer vacations from her studies at Wellesley College.

[5] McCreary appointed a tax commission to study the revenue system, and the Board of Assessments and Valuation made a more realistic appraisal of corporate property.

[5] McCreary created executive departments to oversee state banking and highways, and a bipartisan vote in the General Assembly established the Kentucky Public Service Commission.

[5][47] He also recommended a requirement for full disclosure of campaign contributions and expenditures, but the majority of legislators in the House of Representatives voted to send it back to the Suffrage and Elections Committee, from whence it was never recalled.

[5] Part of the reason for the inefficacy of the 1914 session was that McCreary was engaged in a three-way primary race for the Democratic nomination to the U.S. Senate.