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When the news broke this week that Donald Trump's campaign is essentially broke, you could have heard a pin drop … were it not for the cries of Mr. Trump's campaign staffers diving wildly to the floor, shouting "Hey, look! It's a pin! I wonder if a sewing implement like that has any commercial value!!"

Federal Election Commission filings revealed on Tuesday that Mr. Trump's organization had a scant $1.3-million (U.S.) in cash on hand at the end of May, down from $2.4-million at the start of the month.

In sharp and shiny contrast, Hillary Clinton is sitting pretty on a much more presidential $42-million, having recently raised $26.4-million. That's about the amount of money a hopeful-for-good-reason candidate should have in her lofty-office coffers at this stage in the game.

Mr. Trump's financial situation, coupled with his low-and-dropping poll numbers, would be alarming for any candidate. But for a man whose campaign is predicated almost entirely upon the notion that he's rich and that he wins, it's just plain awkward.

On top of everything else, Mr. Trump has talked a lot about the fact that he's footing the bill for his presidential-run-devolving-to-a-lurch and that he's a great businessman. "By self-funding my campaign, I am not controlled by my donors, special interests or lobbyists. I am only working for the people of the U.S.!" he has tweeted, although he has to date taken in $17-million in donations. Which isn't a lot – but that's not for lack of trying.

Mr. Trump is more self-mythologizing than self-funding. It all looks to be a bit of a shell game. The $45-million or so he has put into his campaign is a loan, not a gift. It's money he can reasonably expect to be paid back, with interest; $6.2-million of that money, the FEC filings showed, has been forked over to companies Mr. Trump owns, and he has, at least in his own mind, advanced his brand.

In the end, "self-financing" as a euphemism for masturbation may well be the single lasting legacy of Mr. Trump's political career, an effort which has so far raised more questions about the state of his finances, both campaign and personal, than it has cash.

If he is worth $10-billion as he (dubiously) claims and could "sell a couple of buildings and self-fund," why on earth hasn't he done that?

"My whole life is about winning. I always win. … I don't lose often. I almost never lose," Mr. Trump said in a Washington Post interview in 2015, and so, by his own logic, those buildings would merely be a loss leader in his latest business – that of becoming President of the United States of America.

So far, however, that high-rise-selling mood has eluded Mr. Trump, and some significant rebranding of the "wealthy," "winner" candidate at short-fingered hand seems to be inevitable. There may be a new persona in the 2016 presidential race, and Broke Donald Trump could be interesting to watch.

I see Broke Donald Trump as The Dude from The Big Lebowski, if The Dude were much less eloquent, and really hated Mexicans, Muslims and women he was not inclined to have sex with at that specific moment.

In my mind, Broke Donald Trump has already moved into his ex-wife's basement, "No, Ivana, I can't take out the trash right now. I am tweeting. Why can't you do it? Sad! Ugh, I am sooo going to build a wall along the basement/rest-of-the-house border and make you pay for it!"

In later campaign-headquarters-renovation news: "Sure, whatever. I'll take out the recycling, too, but the wall just got 10 feet higher!"

Broke-loser-but-still-up-for-being-president Donald Trump's next stump speech will be given from the parking lot of a 7-Eleven. "We just don't pick great lottery numbers any more. I have the best numbers!" I see him saying, sheepishly pocketing an assortment of misnamed scratch-and-wins and free mints from the steakhouse across the road.

I predict collect calls asking for campaign donations. "Hey, Sheldon, it's Donald! I was wondering, so, umm, I'm doing this run-for-president thing, and I was calling to see if you wanted to make a donation. Also, did you guys change your Netflix password?"

"Nope, Sheldon, I am not in Cleveland. Just back at headquarters. It's cooler in the basement anyway, and the team and I thought we'd do some 'staypaigning' this summer."

"My Twitter has become so powerful that I can actually make my enemies tell the truth," he will proudly announce, again, at his next rally, this time adding: "you know, when I can get the WiFi at Starbucks to connect" and – turning to a Secret Service agent – "Do you mind tethering me for a second?"

I'm curious to see how the campaign slogan "I will make America great ramen Cup Noodles again just as soon as one of the golf shirts I put on Craigslist moves. Vintage!" resonates with the people.

Every meeting Mr. Trump takes with evangelical lobby groups, whom he has assured "can trust me on traditional marriage," will still end, as this week's did, with him promising to defund Planned Parenthood, but as Broke Donald Trump, he'll now also pat at his pockets somewhat manically, as if they're on fire and say, "Damn, it looks like I left my wallet in my other coat. Mind helping a great negotiator out?"

I look forward to all this, although less so to all the angry e-mails I get every time I give in to temptation and write about Donald Trump, but I can't stop myself and it's done now.

Most of the correspondence I receive on this matter is more an attack on Ms. Clinton or President Obama than it is a defence of Mr. Trump, which is telling, as are the extremely varied spellings of Benghazi offered in these missives.

Apparently, different spellings of Benghazi are the only kind of diversity this particular demographic embraces, but, man, do they embrace it.

A notable number of the attacks I receive also use the term "postmenopausal" as a pejorative, in reference to Ms. Clinton, so let me nip that one one in the bud now; look, guys, it's not ideal, and a number of good candidates will be excluded, but if you really want to use lack of menses as a disqualifier for high office, I think we can work with this.

And no, Donald, bleeding credibility, campaign managers and cash wouldn't count.

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