Politicians who always narrowly lose

[Vosem]

Dino Rossi is the paradigmatic example here of someone who always performs really well given the circumstances but never actually wins, ever.

In terms of someone who kept being associated with losing campaigns but whose career kept not dying, John Tory before he was elected Mayor of Toronto in 2014 had an amazingly bad track record, being closely involved with the 1985 Ontario PC campaign (their first defeat in decades), the 1993 national PC campaign (when the party collapsed never to recover), and then personally running for Mayor of Toronto in 2003 (and losing embarrassingly) and then also personally losing the 2007 Ontario general election as PC leader (embarrassingly) and a by-election in a safe seat in 2009 (embarrassingly).

Then somehow he came back from that to be a pretty successful Toronto Mayor for a decade before randomly resigning because of a sex scandal.