From the Ward County Independent, November 3, 1910.
Remarked as one of the "most brilliant young lawyers in the state" at the time of his candidacy for Ward County judge, Gaius Sibley Wooledge was a native of Wisconsin who found prominence at the North Dakota state bar. Settling in that state in the early 1900s, Wooledge would be a candidate for Ward County judge and state's attorney but lost out at the polls. Following an unsuccessful run for state attorney general in 1916 and 1918, Wooledge's political fortunes changed, as he was elected as a delegate to the Republican National Conventions of 1920 and 1932, and in 1922 became chairman of the North Dakota State Democratic Committee.
The son of Braman Henry (1848-1887) and Emma (Dillon) Wooledge (1856-1937), Gaius Sibley "Gay" Wooledge was born in Neenah, Wisconsin on July 22, 1880. A student in the public schools of Antigo and Madison in that state, he continued to study at the University of Wisconsin, where he earned his B.A. degree in 1904. He later attended that university's law school and undertook private study before being admitted to the state bar in 1905.
After being licensed to practice Wooledge left Wisconsin for North Dakota and established himself in the town of Anamoose. He resided there until 1907 when he removed his practice to Kenmare in Ward County. He was a member of the firm Murphy and Wooledge and first entered public life in the late 1900s with his time as city attorney for Kenmare. His full dates of service remain unknown, though it is known that he was "deposed from office" by Kenmare mayor E.C. Tolley in 1909.
Success came quickly to Wooledge at the state bar, and by October 1910 had become a rising figure in local Democratic circles. This would lead to his being chosen to introduce the great William Jennings Bryan during the latter's visit to Minot, North Dakota on October 27th, where he gave an address before 3,000 people. 1910 proved to be a busy year for Wooledge, as he had announced his candidacy for Ward County Judge earlier in the year. After winning the Democratic primary that July, Wooledge faced off against incumbent judge Nehemiah Davis, who'd first been elected in 1904. That November Wooledge placed second in the vote count, with Judge Davis continuing to serve until 1912.
A year following his defeat Wooledge left Kenmare for Minot, where he partnered with state representative Arthur Thompson in the law firm of Thompson and Wooledge. In June 1912 Wooledge married in Minot to Alice Metheny (1880-1940), a resident of Brookings, South Dakota. The couple subsequently honeymooned in the twin cities, and took "a trip down the great lakes." The couple were wed until Alice's death and had one son, Read Matheny Wooledge (1913-1934).
In 1914 Wooledge re-entered politics when he announced his candidacy for president of the Minot city commission. One of three candidates vying for the office, Wooledge polled third, with victory going to local lumber merchant Chris H. Rudd. Undeterred by the loss, Wooledge announced his candidacy for State's Attorney for Ward County later that year. Notices touting his candidacy appeared in several editions of the Ward County Independent in the fall of 1914, where Wooledge outlined his platform including curtailing unnecessary expenses in the state's attorney office. These expenditures included the salary of an assistant state attorney, the abolition of special prosecutors, and "no private practice at County's expense." He would go on to remark:
"Lastly, the states attorney should take care of all county business before any private business. He should stay on the job the year round and at all times remember that he has been hired and paid by the taxpayers of this county to take care of the county business, promptly and efficiently, and yet with little expense as possible."
From the Ward County Independent, October 2, 1914.
As with his two previous candidacies, Wooledge went down to defeat that November, being defeated by incumbent Republican Ragnvald A. Nestos (1877-1942), 1,784 votes to 1,172. Nestos' later political career saw him enter the Republican primary for U.S. Senator, and from 1921-25 served as Governor of North Dakota.
Two years after his run for state's attorney Wooledge set his sights on a lofty goal, the attorney generalship of North Dakota. After winning the June Democratic primary, he opposed Republican candidate William Langer (1886-1959). That November Wooledge lost out in a lopsided contest, polling 21,113 votes to Langer's 79,783, with Langer carrying every county in the state. Wooledge was dealt another loss to Langer in 1918 when he was again a candidate for attorney general, garnering 31,973 votes to 55,339. William Langer's political career continued to soar following his two terms office, serving terms as Governor of North Dakota and from 1941-59 represented that state in the U.S. Senate.
Following these losses, Wooledge continued with his law practice in Minot, and in 1917 entered into a four-year term as Minot city attorney. He would partner with former Minot mayor Daniel Greenleaf in the firm of Greenleaf and Wooledge, specializing in "Corporation, Real Estate, and Banking Law." From 1918-21 Wooledge held the additional role of legal representative for North Dakota under Alien Property Custodian A. Mitchell Palmer, who would later be named as U.S. Attorney General under President Wilson.
Wooledge's political fortunes improved in 1920 when he was elected as chairman of the North Dakota delegation to the Democratic National Convention in San Francisco, where James M. Cox was nominated for the presidency. Wooledge would announce his candidacy for the state supreme court in the spring of 1922, and following his defeat for that office achieved a measure of consolation that September when he was elected as chairman of the North Dakota Democratic Executive Committee.
Two years into his tenure Wooledge clashed with committee secretary Henry Holt, and in February 1922 was ousted from the chairmanship at a meeting of state committee members. Following his removal, James Campbell was designated the new state chairman. Crying foul and calling the vote invalid, Wooledge saw the North Dakota democrats split into two camps, a pro-Campbell group and a pro-Wooledge group. These camps continued their split through the early part of that year, with newspaper reports designating both Wooledge and Campbell as chairman. On April 29, 1924, both camps attended the state democratic convention, where party harmony prevailed, with Wooledge (with the consent of James Campbell) calling the convention to order and naming the credentials committee. He would designate Campbell as chair of that committee, and continued as democratic state chairman into the latter part of 1924.
From the Ward County Independent, June 27, 1922.
After leaving the chairmanship, Wooledge continued to be politically active, serving as an alternate delegate to the Democratic National Convention of 1932, and in that year was named temporary chairman of the North Dakota Democratic Convention held in New Rockford. He continued membership on the state democratic committee and held the post of Ward County democratic committee chairman well into the 1950s. Wooledge died at his home in Minot on July 31, 1966, shortly after his 86th birthday. His wife and son predeceased him, and all were interred at the Riverside Cemetery in Fargo, North Dakota.
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