[5] After the abolition of slavery in the United States, Warfield returned home frequently to help run his family's estate.

In 1888, Warfield founded The Daily Record as a newspaper covering finance, commerce, business, and court matters or legal proceedings.

[citation needed] Through his father's line, he was a third cousin to the Duchess of Windsor (originally named/née Bessie Wallis Warfield, later Wallis Warfield Simpson of Baltimore), wife of the abdicated king of the United Kingdom, King Edward VIII, later Prince Edward, Duke of Windsor.

[8] In 1890, after his removal from the position of Surveyor, Warfield founded the Fidelity and Deposit Company, where he served as president until his death.

[citation needed] In September 1903, Warfield served as the main speaker and orator for the ceremonies dedicating the Lt. Col. William H. Watson (1808–1846) Monument.

Though it was apparent that the party bosses did not hold him in favor, he again sought the nomination in 1903, openly discouraging African Americans' ability to vote.

[citation needed] The bill easily passed the Democrat-controlled General Assembly, but Warfield refused to support the proposed amendment and delayed placing it before the voters.

Warfield's actions in this affair further alienated him from the Democratic machine in Maryland, which was openly hostile towards him by the time he left office.

He argued this before the General Assembly in 1906, and direct election of senators was eventually codified into national law with the Seventeenth Amendment to the United States Constitution.

Another historical "final act" for Wakefield's term as Governor was the success of a long search and process by the United States' then-Ambassador to France to discover the whereabouts of an American naval hero's burial site in Paris, and to oversee the return of the body of American Revolutionary War Captain John Paul Jones to a specially-prepared marble crypt at the U. S. Naval Academy in Annapolis, Maryland.

Warfield was proud of his family's Confederate legacy, representing Maryland in reunions and events like the 1911 Southern Commercial Congress in Atlanta.