The source said Henry had been approached to stand for office six times over the years.
"In the last two years he has been presented with three absolute plans, but he has always ruled them out. This time, however, he's not ruling it out."
In terms of timing, a run in 2016 would fit in nicely with Henry's career plans.
The Diary understands he does not see himself fronting a late-night show long term and would be ready to walk away from TV.
But a move to mayor would mean a significant pay cut.
"There would be perks, like hotel upgrades and liaisons in civic buildings," laughed the well-placed source.
Henry has been a vocal opponent of Mayor Brown and his plans for rapid rail and rates increases. His Tory leanings would please the current Government, which has had an uneasy relationship with Brown.
"It would be time for Auckland to have some fun," said the source. "Not contrived fun, like the occasional pyrotechnic display, but real fun. This city deserves it."
WATSON'S TWITTER FAUX PAS
He's new to Twitter and has taken to the social media platform with gusto, but Eric Watson was exposed by Warriors hooker Nathan Friend this week when his tweet offensive went awry.
The Warriors boss, who is in a public stoush with the club's co-owner, Sir Owen Glenn, was keen last week to reveal how committed he is to his team.
He hit the airwaves and column inches to convey his love for the beleaguered franchise.
However, this week, in replying to a fan who asked about Friend's future with the club, Watson tweeted that the NRL's top tackler "is signed [through] till end of 2015 which is fantastic w[ith] his work rate".
However, that is not so.
"I'm currently on my last year but would love to continue on if given the option," Friend corrected his boss on Twitter. He is off-contract at season's end.
That prompted a quick moonwalk by Watson. "Sorry mate, fat fingers with my typing!", Watson replied to Friend on the public forum. "You are an outstanding player, love and respect your commitment."
Evidently not enough to know when his contract ends.
Fox Sports said 33-year-old Friend "is determined to play on next year but the Warriors' contractual silence thus far has been deafening, leaving Friend a man in limbo".
Watson's last tweet on the matter was crystal: "He's signed till the end of the year."
What happens to Friend after that is not yet clear.
Warriors PR manager Richard Becht said the bungle was an innocent mistake. "Eric did know. He just made an error."
ROMANCE IS COOKING
Celebrity chef Pete Evans is the guest of honour at an $800-a-plate dinner (including lodging) at luxury hotel Cape Kidnappers in Hawkes Bay on Saturday, where he will no doubt toast his impending betrothal to former Kiwi glamour girl Nicola Robinson (nee Nicky Watson).
The pair have been engaged for two months and are planning a wedding next summer. They are shopping for a pounamu engagement ring over Easter.
It will be the second marriage for Nicky, who separated from Eric Watson in 2003.
She has been romantically linked to Matthew Ridge, Ali Williams and Sydney nightclub boss Justin Hemmes.
Evans, a star of My Kitchen Rules, has two daughters, Indii and Chilli, to former partner Astrid Ellinger, with whom he had an 11-year relationship.