I've long toyed around with this idea but was never quite sure of how best to format it when toying around with lists, and have long struggled to write a Vignette on the subject. And then Bob dropped that Electoral History Billy Hughes, which not only had a similar theme but of course, struck me as the best way to go about showing it. So here goes.
After Trying Everything Else
The Electoral History of Winston Churchill
Jan 1 1897 - Dec 31 1897: National “Gold” Democratic Member, New York State Assembly, Kings County
1896: National "Gold" Democratic (48%), "Bryanite" Democratic & Populist (29%), Republican (21%), Socialist Labor (2%)
1897: "Bryanite" Democratic (41%), National "Gold" Democratic (34%), Republican (22%), Socialist Labor (3%)
Jan 1 1898 - May 5 1898: Private Citizen, Reporter, New York Journal
May 5 - November 14 1898: Officer United States Army, 71st New York Volunteer Regiment
May 5: Second Lieutenant,
July 4: First Lieutenant (Brevet Captain)
November 14: Reversion to First, Lieutenant, Discharged
November 14 1898-1901: Private Citizen, Reporter, New York Journal, New York Evening Journal, Brooklyn Eagle, New York Times
1901-1903: Democrat, Congressmen for New York 6th Congressional District
1900 def. James R. Howe (Republican)
1903-1909: Republican, Congressmen for New York 9th Congressional District
1902: Mitchell May (Democratic)
1904: Daniel D. Whitney (Municipal Ownership) George H. Lindsey (Democratic)
1906: Robert Baker (Democratic)
1908: Robert Baker (Democratic)
1909-1913: Republican, Secretary of the Navy under William H. Taft
1912: Republican, Electoral College (replacement) nominee as Vice President
Electoral College 1912:
T. Woodrow Wilson / Thomas R. Marshall (Democratic) EV 435
Theodore Roosevelt / Hiram Johnson (Progressive) EV 88
William H. Taft / [James S. Sherman], Winston S. Churchill (Republican) EV 8
Eugene V. Debs / Emil Seidel (Socialist) EV 0
1913-1915: Private Citizen, Reporter, New York Times, Magazines
1914: Republican, Candidate for New York 6th Congressional District
1914 defeated by John A. Hennessy (Democratic)
1915-1917: War Correspondent, New York Times: Palestine, Mesopotamia, Western Front
1916: Republican, Primary Candidate for United States Senate Seat, New York
1916: Robert Bacon (151,398), Winston S. Churchill (146,342)
1917-1919: Officer National Army - United States, Multiple Postings
April 4 1917: Commissioned Major, 69th Infantry Regiment, NYNG
October 14: (Brevet) Lt. Colonel 165th Inf. Regiment
March 6 1918: Lt. Colonel, 83rd Brigade Staff
June 1: Lt. Colonel 42nd “Rainbow” Division Staff
August 20: Colonel 42nd “Rainbow” Division Staff
November 5: (Brevet) Brig. General, Planning Staff, Commander AEF
April 5 1919: Reversion to Colonel, Discharge
1919-1920: Private Citizen, Reporter, Magazine Writer, Historian
1920: Republican, Primary Candidate for Governor of New York
1920: Winston S. Churchill (259,310), George F. Thompson (154,693)
1921-1922: Republican, Governor of New York
1920: George R. Lunn (Democratic), Joseph D. Cannon (Socialist / Farmer-Labor)
1923-1935: Republican, Senator for New York
1922: Royal S. Copeland (Democratic), Algernon H. Lee (Socialist-Farmer-Labor)
1928: Edwin Corning (Democratic), Robert B. Minor (Socialist-Farmer-Labor)
1934 New York Republican Primary: Dorothy Frooks def Winston S. Churchill
1924: Republican, Candidate for Presidential Nomination
First Ballot:
Gifford Pinchot: 314
Winston S. Churchill: 297
William E. Borah: 133
Robert M. La Follette: 94
Herbert C. Hoover: 81
Scattered: 190
Fifth Ballot:
Herbert C. Hoover 884.5
Winston S. Churchill: 155.5
Henry Ford: 54
Robert M. La Follette: 15
1924 Republican, Candidate for Vice Presidential Nomination
First Ballot (After Shifts)
Robert L. Bullard: 734.5
Irving L. Lenroot: 247
Winston Churchill: 45
Scattered 82.5
1932 Republican, Candidate for Presidential Nomination
First Ballot
Willian E. Borah: 362
Winston S. Churchill: 317.5
Ogden L. Mills: 244
Theodore Roosevelt, Jr.: 167.5
Scattered: 76
Seventh Ballot (After Shifts)
Winston S. Churchill: 887.5
Theodore Roosevelt, Jr.: 187.5
Alfred E. Landon: 62
Scattered: 8
1932 Republican, Nominee for President of the United States
Electoral College 1932:
Upton B. Sinclair, Jr. / James N Garner (Democratic) EV: 358
Winston S. Churchill / Frederick Steiwer (Republican) EV: 173
William Z. Foster / James P. Cannon (Workers’) EV: 0
1935-1940: Private Citizen, Newpaper and Magazine Writer, Historian, Author
1941-1945: Republican, President of the United States
1940 Republican, Candidate for Presidential Nomination
First Ballot
Robert R. McCormick: 276
Gerald P. Nye: 249.5
Robert L. Bullard: 192
Winston S. Churchill: 157.5
Scattered: 125
Sixth Ballot (After Shifts)
Winston S. Churchill: 990
Robert L. Bullard: 8.5
Hamilton S. Fish, Jr. II: 1.5
1940 Republican, Candidate for President of the United States
Electoral College 1940:
Winston S. Churchill / Roscoe C. Patterson (Republican) EV: 286
Huey P. Long / Francis T. Maloney (Democratic) EV: 244
Fiorello H. LaGuardia / Van A. Bittner (Industrial Democracy) EV: 1
Robert L. Bullard / Claire E. Hoffman (Independent)
1944 Republican, Candidate for Presidential Nomination
First Ballot
Winston S. Churchill: 1011
Gen. Douglas MacArthur: 34
Harold E. Stassen: 12
1944 Republican, Candidate for President of the United States
Electoral College, 1944
Albert B. “Happy” Chandler / James M. Curley (Democratic) EV: 283
Winston S. Churchill / Roscoe C. Patterson (Republican) EV: 228
Harris A. Brandborg / Leo Krzycki (Industrial Democracy) EV: 20
1945-1945: Ambassador-at-Large and Personal Representative of the President
1946-1951: Permanent Representative to the United Nations
1951-1964: Private Citizen, Author, Historian, Magazine Writer
Footnotes, if everyone doesn't mind in the morning. Its going to cover everything from the long list of enemies he develops you might be able to pick some out from just the list, as well as his marriage, and various tribulations.