Abraham Lincoln is often incorrectly credited around the Internet with losing all of his elections - up to 7 of them. While Lincoln definitely had his losses, this appears to be stretching the truth. The Lincoln website shows his failures here:
AUGUST 6, 1832
Loses first race for Illinois House of Representatives
DECEMBER 3, 1838
Loses bid for Speaker of the Illinois House of Representatives
FEBRUARY 8, 1855
Loses bid for Senate when Illinois legislature elects Lyman Trumbull
http://www.abrahamlincolnonline.org/lincoln/education/polbrief.htm
Snopes examines this "failure" exaggeration here:
One would think the facts of Lincoln's life should be a good enough story for anyone, but no, apparently the truth isn't sufficiently inspirational; it has to be shaped and molded into glurge that depicts Lincoln as a man who endured constant failure and defeat from the time he was born until he was elected President.
http://www.snopes.com/glurge/lincoln.asp
So does anyone fit this description?
Apparently not. After an exhaustive search, I can't find anyone who fits this description. There are indeed five presidents who never won an election: Gerald Ford, John Tyler, Millard Fillmore, Andrew Johnson and Chester A. Arthur.
http://uspolitics.about.com/od/CampaignsElections/fl/5-US-Presidents-Who-Never-Won-a-Presidential-Election.htm
This website has a list of all politicians losing the most elections, so if you have someone in mind, check for their name there.
http://politicalgraveyard.com/special/lostmost.html