He came to lead the conservative coalition in the Senate, and opposed President Franklin D. Roosevelt, largely blocking most liberal legislation after 1937.

Byrd succeeded to what had been the Virginia Democratic Party organization of U.S. senator Thomas Staples Martin, who died in 1919.

The Byrd Organization also benefited from limiting the political participation of blacks and poor whites in Virginia by means of poll taxes and literacy tests, but managed to defeat opposition ranging from New Deal governor James H. Price to gubernatorial and senatorial candidate Francis Pickens Miller.

His parents, Eleanor Bolling (Flood) and Richard Evelyn Byrd Sr., moved the young family to Winchester, Virginia, the same year.

[citation needed] Young Harry Byrd's father became wealthy as an apple grower in the Shenandoah Valley, and publisher of the Winchester Star newspaper.

Harry initially attended the public schools, but received most of his education from the private Shenandoah Valley Academy in Winchester.

Their uncle Henry De La Warr Flood served in the House of Representatives of the U.S. Congress from Appomattox County from 1901 to 1921.

Another uncle from Appomattox County, Joel West Flood, served as that county's Commonwealth Attorney (1919 to 1932), in the U.S. Congress (beginning in 1932 to fill the vacancy caused by the death of Henry St. George Tucker), and as a state appellate Judge (of the Virginia Fifth Circuit, based in Richmond, from 1940 to 1964).

Virginia's first postwar legislature had affirmed those debts at original terms (highly favorable to bondholders, which by then were mostly out-of-state purchasers at rates a small fraction of par value).

They lived with her parents in Winchester until 1916, when he built a log cabin, named Westwood, in Berryville at a family-owned orchard, and they moved there.

The company refused to ship more newsprint on credit, so Byrd cut a deal to make daily cash payments in return for ownership.

[citation needed] Byrd also owned extensive apple orchards in the Shenandoah Valley and an apple-packing operation which was among the largest on the East Coast.

[15] In the 1950s, Edward P. Morgan's assistant visited Byrd's Northern Virginia farm during the apple harvest and was outraged by the living conditions of the migrant workers.

In 1923, Byrd was sued by the Virginia Highway Contractors Association because he said their activities "by combination and agreements may be very detrimental" to the State.

[This quote needs a citation] The court dismissed the suit, stating the criticism was legal, imposing all costs upon the association.

[citation needed] As governor, serving a term from 1926 to 1930, Byrd pushed through constitutional amendments that streamlined the state government and allowed for more efficient use of tax dollars.

"He advocated building roads to state shrines such as Jamestown and Monticello and called for historical markers along roadways, the first of which appeared in Fredericksburg.

He held regional meetings to bring about closer cooperation between state and county road officials, prophesying that the road system could be completed within ten years through such cooperation... A tour of the highway system convinced him of the progress being made in extending the arterial network.

[citation needed] Education was not on his agenda, and state spending for public schools remained very low until the late 1960s.

Byrd authored and signed the "Southern Manifesto" condemning the 1954 U.S. Supreme Court decision in Brown v. Board of Education.

Byrd and his colleague Carter Glass invoked senatorial courtesy to stop President Franklin Delano Roosevelt's nomination of Floyd H. Roberts to a federal judgeship in Virginia in 1939.

As war loomed in 1941 Congress approved his proposal for a joint House–Senate committee to look into ways of eliminating nonessential expenditures.

By late September, the Joint Committee on Reduction of Non-essential Federal Expenditures was in operation with Senator Byrd as chairman; it built his national reputation as an economizer.

He often broke with the Democratic Party line, going so far as to refuse to endorse the re-election of liberal President Harry S. Truman in 1948.

He voted against public works bills, including the Interstate Highway System, and played a key role in the passing of the 1964 Revenue Act.

According to the American political historian Steve Neal, at one point during the Democratic National Convention Byrd was offered the vice-presidential slot in exchange for instructing his 24 delegates to vote for Franklin D. Roosevelt, but declined because he believed he had a chance of winning the presidential nomination.

At the 1944 Democratic National Convention, Southern delegates opposed to Roosevelt's New Deal and racial policies nominated Byrd as the party's presidential candidate.

Heinemann concluded that although Byrd was a greatly-talented and intelligent politician, one who came to dominate Virginia politics and substantially impact U.S. politics for decades, he frequently overlooked many other issues he could have helped address in favor of defending white supremacist policies and resisting the changing of the times, consequently squandering his long-term reputation on a doomed battle to preserve de jure racial segregation in the U.S. A New York Times editorial following Byrd's retirement from the U.S. Senate in 1965 gave a similar assessment: "A talented man, Byrd chose to stand outside the broad currents of his time and to set his face against the future...

[38] The Blue Ridge Parkway bridge over the James River in Big Island, Virginia was named and dedicated to him in 1985.

Although many acres of Byrd's former orchards are now commercial and residential properties, Rosemont is now open to the public as a bed and breakfast, as well as event venue.