I think people get Olivia Chow backwards.
They talk about her as if she's a failed, incompetent politician: someone whose entire career was built around being Jack Layton's wife.
That's nonsense for three key reasons:
Thing One: She held elected office before she'd even met Jack. Jack did not start her political career, nor did she inherit her machine from him.
Thing Two: She held elected office even when Jack didn't. In particular, after Jack Layton's failed 1991 mayoral bid, he was locked out of city hall -- and here's the thing: formal mayor candidates have a way of disappearing. When's the last time you heard of George Smitherman? How about Jane Pitfield? Susan Fish? Rocco Rossi? Joe Pantalone? These people all had serious, big-time political jobs before running for mayor (cabinet ministers, deputy mayors, party executives...), and all of these people managed to run serious, big-time mayoral campaigns which attracted oodles of attention and media exposure and legitimacy, and all of them fell right off the map after losing, never heard from again except as curiosities. ("Former mayoral candidate Sarah Thompson...")
Is there reason to believe that Jack Layton would have been different?
What kept Jack Layton from facing a similar fate was his relationship with Olivia Chow. Chow won her Metro Council seat handily, and that not only kept Jack in the spotlight as her spouse (the two have always been handled as an item, a political power couple), it had the effect of keeping his machine warm as well.
Yet nobody ever talks about Jack riding Olivia's coattails. Funny how that works, eh?
Thing Three: Yes, absolutely, Olivia has lost elections. But this is substantially because she has deliberately chosen to do things the hard way.
The easy way to become a career politician is to lock down a city council seat and stay there forever. Incumbents are singularly safe, and Olivia had the added advantage of being beloved: in every municipal election she's contested, she scored an outright majority, often 70% or more of the vote. If she was just cynically looking to collect a salary and keep her name in the papers with as little work as possible, this is the route she'd have taken: become a council fixture, maybe write a book or do some adjunct teaching on the side, but basically bunker down and become a lifer.
Instead, she chose more ambitious goals.
She chose to run for provincial and federal office, and she almost uniformly exceeded expectations. In 1997, for example, with the NDP holding no seats anywhere east of Manitoba, she ran in Trinity--Spadina and came within 2000 votes of beating the Liberal incumbent. (For contrast, Jack ran in what was then Broadview--Greenwood and came up 10,000 votes short.)
Losing doesn't necessarily mean she was incompetent: I'd suggest it has a lot to do with picking more challenging fights and taking on tougher opponents, rather than contenting herself with the comfortable and easy pickings of a councillor-for-life gig. Chow has chosen to fight and lose rather than chalk up easy victories, and I think that's more interesting than "WHAT A LOSER, ALWAYS LOSING".