An “evening of fun” may have Rob Ford in trouble again.

This kind of fun is in the form of a $300-per-ticket fundraiser. The problem is that Ford is advertising the money-making venture on his regular e-mailed newsletter to constituents in Etobicoke (and possibly elsewhere, but we’ll come back to that).

The fundraiser appears to be an effort to recoup campaign spending after the Fords both ran for mayor (remember that?). To be held at the Ford matriarch’s house on May 14, at $300 a ticket, the invitation promises a $225 rebate from the city — which is standardized through election rules.

If you run in a city election and end the nearly year-long ordeal in the red, the city lets you extend your campaigning past the deadline until you make up the cash or up until June 30.

Both Rob and Doug filed for extensions, reportedly claiming they have hundreds of thousands of dollars in expenses.

Still, the invitation itself doesn’t make clear where the fundraiser money is going. The newsletter also promotes the continued sale of bobbleheads in Ford’s likeness, which he has promised “net proceeds” to Mt. Sinai and Humber hospitals, where he has received cancer treatments.

There are a couple of issues with the fundraiser’s promotion — but first, a small recap.

Ford had more integrity commissioner investigations and questionable conduct accusations against him then any other council member last year, so it would be difficult to argue he’s not at least aware of the rules.

City election rules prevent city councillors from using city resources in the course of the election campaign. Most councillors send out regular newsletters — either snail mail or e-mail — to their residents. But they aren’t allowed to actively campaign in those writings.

The city’s code of conduct for councillors also prohibits members from using city resources other than for official city business.

Advice from the integrity commissioner on the code of conduct specifically spells out that councillors cannot use official letter head to promote events unrelated to city affairs.

“The principle here is the maintaining of public confidence in councillors who demonstrate financial responsibility and accountability for the use of city resources,” the advice reads.

But here’s where the problem is really spelled out: “No member shall use the facilities, equipment, supplies, services or other resources of the City (including Councillor newsletters and websites linked through the City’s website) for any election campaign or campaign-related activities.”

The city rules also prevent anyone from participating in election work during hours they are paid by the city — meaning it’s against the rules for Ford’s staff to assemble and distribute information about the fundraiser or to prepare for the fundraiser in any way during the day.

On my way into city hall this morning, I ran into Ford’s executive assistant, Dan Jacobs, in the rotunda. I told him we were hearing concerns about the newsletter and that it potentially breaks city rules.

Jacobs told me Ford and their office don’t actually produce the newsletter themselves and that it is sent by “volunteers.”

I personally get the newsletter. That’s because when Ford backed out of the running to be mayor, swept the Ward 2 (Etobicoke North) race and posted a brand new website torontorobford.ca, I signed up for email updates. As you might know, Ford’s office stopped sending the Star any itineraries, statements or heads up on press conferences when he was mayor. During the campaign my colleagues and I sporadically got emails telling us of upcoming events. This was a way to hear from Ford on issues he cares about.

Ford’s new website has his boilerplate biography (crack scandal omitted), links to his official social media accounts and lists his city hall office on the contact page.

A search for who registered the domain name for the site returns no insights. It’s set up through popular go-between GoDaddy. The site itself is managed through wix.com, which has a newsletter service used for Ford’s mail blasts.

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It should be noted that at least one person – I received a copy of their note to their local councillor (who is not Ford) – has complained that they never signed up to be on Ford’s mailing list. That’s another problem that has persisted since earlier in the campaign and one that has not been resolved.

But when I asked Jacobs whether Ford and the office is ducking any responsibility for the newsletter — does no one in the office even look at it before it goes out? He didn’t deny they were involved.

What’s more, the newsletter arrived in my inbox at 5:01 p.m. yesterday via the wix.com setup but “on behalf of Councillor Rob Ford [councillor_ford@toronto.ca]” – which is, of course, Ford’s official city hall e-mail.