Calvert is known to be an outspoken councillor around the table. She's a nitpicker for detail while Lester is more of a big-picture man.
The mayoral race would certainly be turned up a notch if she went ahead with a bid.
Calvert, an independent who uses the colour aubergine for her campaign because it represents "a good blend of blue and red topped off with green", is facing the Labour machine at home in her ward and in any mayoral bid she makes.
Labour is standing Rebecca Matthews in the Onslow-Western Ward.
Lester has already made thousands of calls on her behalf and has joined her on door-knocking expeditions.
The ward is a stronghold for current councillors Simon Woolf and Andy Foster, leaving Calvert as a target.
But Woolf and Calvert have presented themselves as quite a team this year.
That relationship would pay off in any mayoral bid Calvert made. By offering Woolf the deputy mayor gig, she'd secure a swell of extra votes.
The most recent example of the tag-team was at a select committee hearing over the bus fiasco where Wellington City Council was called in for another "please explain".
It's understood Calvert and Woolf organised to speak on a bus commuter survey they conducted without telling Lester, in a bid to take him by surprise.
It begs the question whether Calvert is trying to do the same with a mayoral campaign.
Her playing coy could be to test the water for a mayoral bid, or it could be a profile-building exercise, or an effort to keep her cards close to her chest.