Later Life
He married in 1870. In the late 1870s, a combination of hard times for farming in general and the death of his child in a sawmill accident drove Simpson to move south, to Barber County, Kansas, where he bought a ranch and a herd of cattle.
In late 1883 and early 1884, a long, hard winter killed his entire herd, and Simpson was reduced to working as the town marshal in Medicine Lodge, Kansas. It was during this time that Simpson, angry at his plight, first involved himself in politics, becoming an organizer for the Union Labor Party, a local offshoot of the defunct Greenback Party (of which he had been a member). He ran as their candidate for the state legislature in 1886 and 1888, but was defeated by the T. A. McNeal of the state's dominant Republican Party.
In 1889, the price of corn, the state's principal crop, dropped precipitously, and it was burned as fuel all across Kansas. Seizing the moment, remnants of the Farmers' Alliance organized into the People's Party, and Simpson joined on. At the convention of the Kansas People's Party, Simpson was easily nominated as the Party's candidate for Congress.
Simpson's Republican opponent was Colonel J. R. Hallowell, an attorney for a railroad who campaigned from the back of a private rail car. Simpson, campaigning on a populist platform of public ownership of railroads, a graduated income tax, the abolition of national banks, and universal suffrage, denounced Hallowell as a pampered scion of wealth whose feet were "encased in fine silk hosiery." Hallowell fired back that having silk socks was better than having none at all. With the help of populist campaigner Mary Elizabeth Lease, Simpson won a new nickname, "Sockless Jerry," and an 8,000-vote margin of victory in the race.
In Congress, Simpson was a forceful advocate for populist causes and became nationally-known as the party's congressional leader. In 1892, he was re-elected by a slim 2,000-vote majority, running slightly behind James Weaver, the party's presidential nominee, who had also managed to seize the Democratic ballot line in Kansas. By 1894, however, the party's fortunes had already started to wane, and he was turned out of office in favor of Republican Chester I. Long in a close race.
Undaunted, Simpson returned in 1896, running hard against Long and upsetting him to win back his House seat. It didn't last, however, and Long defeated him once again in the election of 1898.
Deciding that he had lost his taste for farming, Simpson moved to New Mexico and took up real estate. A few years later, he suffered a debilitating brain aneurysm. Realizing that he probably didn't have much time left, he boarded a train back to Kansas. He died in a Wichita hospital on October 23, 1905. He is interred in Maple Grove Cemetery.
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