[4] Simmons began his career as a reporter for the Pensacola Daily Press before moving to the Chicago Defender, where the growing popularity of his columns made him that newspaper's highest-paid employee and a staple of its front page.

"[4][5] As part of a scheme by the Military Intelligence Division to elevate the prominence of patriotic black leaders as a counter to the perceived threat of subversion within the African-American community, Simmons was engaged in a nationwide series of lectures and speeches.

[6] Simmons quickly established a reputation for unparalleled oratorical skills, with William Jennings Bryan calling him "one of the great orators of the world."

Promoted in advertisements as "America's greatest orator," W. Herbert Brewster even attributed a 1916 speech by Simmons as his motivation "to be somebody someday.

Today the nation faces danger from a foreign foe, treason skulks and stalks up and down our land, in dark councils intrigue is being hatched.

[10] A lifelong Republican, Simmons was the driving force behind the party's lock on the African-American vote from the early 1900s through to the Great Depression.

He formed part of the so-called "Old Guard," a triumvirate of black party insiders that wielded significant backroom influence within the GOP and which also included Perry Wilbon Howard and Robert Reed Church.

According to a report in the Pittsburgh Courier the day after the nomination, "his exit from the platform was blocked by senators, committeemen, governors, and others high in the public life who sought to touch the hem of his garment.

"[11] In 1936 Simmons was appointed chair of the Negro Speakers Bureau of the Republican Party, a group of prominent African-American GOP activists, by national committee chairman John Hamilton.

In 1929, he mounted a primary challenge against Oscar Stanton De Priest for U.S. House of Representatives from Illinois's 1st congressional district.