He was praised by contemporaries and by authors Shavin and Galphin as a civic promoter, political strategist, and captivating speaker,[2] and by Atlanta journalist Frederick Allen as a visionary.

[3] However, in modern times, Grady's arguments for the need for white supremacy in the post–Civil War South have resulted in his legacy being seen as mixed and overtly racist.

His father William Sammons Grady was a Confederate States Army officer who died of wounds received at the Battle of the Crater.

In 1867, he became a member of the Phi Kappa Literary Society, and later attended the University of Virginia to study law, but became especially interested in the Greek and Anglo-Saxon languages, history, and literature, which led to a career in journalism.

In 1882 he was elected as the first Grand Alpha (National President) from the south after the union of the Northern and Southern Orders of Chi Phi in 1871.

In 1880, with $20,000 borrowed from Cyrus West Field, Grady bought a one-fourth interest in the paper and began a nine-year career as one of Georgia's most celebrated journalist-publishers.

In the tumultuous decades following Reconstruction, when hatreds lingered and many whites worked to re-establish white supremacy, Grady popularized an antithesis between the "old South" which "rested everything on slavery and agriculture, unconscious that these could neither give nor maintain healthy growth," and a "new south" – "thrilling with the consciousness of growing power and prosperity:" The new South presents a perfect democracy...; a social system compact and closely knitted, less splendid on the surface, but stronger at the core; a hundred farms for every plantation, fifty homes for every palace; and a diversified industry that meets the complex needs of this complex age[8]as he said in an 1886 speech in New York.

Grady was also praised for his great passion for political oratory (he supported Prohibition and a Georgia veterans' home for disabled or elderly Confederate soldiers), commitment to the new peace, and well-known sense of humor.

Grady spotted General William T. Sherman in the audience, the celebrated Yankee soldier who was credited with defeating and burning much of Georgia, and particularly Atlanta, on his infamous march to the sea.

Without missing a beat, Grady acknowledged the general by noting that the people of Georgia thought Sherman an able military man, "but a mite careless about fire."

It was a poor "one gallus" fellow, whose breeches struck him under the armpits and hit him at the other end about the knee—he didn't believe in decollete clothes.

The Georgia Historical Quarterly brought that story full circle, noting Grady's response to the eventual growth of quarries in Pickens County.

By the time he made it to the depot at Atlanta, he was too exhausted to appreciate the reception prepared for him and had to be shielded from the crowd and escorted home by his physician.

[18] In 1931 Grady was the first person inducted into the Georgia Newspaper Hall of Fame, memorialized via a bust by artist Steffen Thomas.

[19] During World War II the Liberty ship SS Henry W. Grady was built in Brunswick, Georgia and named in his honor.