Dean Obeidallah, a former attorney, is the host of SiriusXM radio's daily program "The Dean Obeidallah Show" and a columnist for The Daily Beast. Follow him @DeanObeidallah. The opinions expressed in this commentary are his.

(CNN) "When the going gets tough, the tough get going," the saying goes. But in Donald Trump's case, that expression could be amended to: "When the going gets tough, Trump files for bankruptcy" -- at least with respect to his ventures that hit especially hard times.

So, given that history, is Trump now dreaming of filing for "bankruptcy" for his presidency considering how objectively bad it's going?

Trump's tale of bankruptcies suggests a big "yes!" First, there was Trump's Taj Mahal Casino in Atlantic City, New Jersey. Despite Trump calling the casino a " fantastic deal ," soon after opening in 1990 the Taj Mahal's business took a nose dive, racking up massive debt. Trump himself guaranteed $833 million of his empire's debt. What did Trump do with things looking so bleak? The Taj Mahal filed for bankruptcy in 1991.

And then during the 2008 recession, Trump's casinos took such a beating that his casino operating group, Trump Entertainment Resorts, had run up over $1.7 billion in debt. So what did Trump do? File for bankruptcy, of course.

All told, Trump-owned companies filed for Chapter 11 bankruptcy protection four times between 1991 and 2009. Asked about this during the presidential campaign, Trump said he had "used, brilliantly, the laws of the country" on behalf of his business.

With that in mind, look at where Trump's presidency is now. It's ugly. I'm talking the Trump Taj Mahal-in-1990 type of stinker.

Take this weekend. Trump had planned to commemorate the one-year anniversary of his presidency by attending an extravagantly priced fundraising dinner for the Trump Victory Fund at his private Mar-a-Lago country club where couples had to pay $100,000 to attend. Instead, Trump was stuck dealing with a government shutdown that has the potential to cause him more political headaches.

Then there are President Trump's approval numbers. Per a new CNN poll released Friday, Trump is sporting a 40% approval rating. How does that compare to other presidents at this point? Trump has the lowest approval rating at the one year mark of any elected president "since modern public opinion polling began."

Then there's the ongoing investigation by special counsel Robert Mueller. As much as Trump has disparaged it , this investigation has found that both Trump's former national security adviser Michael Flynn and Trump campaign foreign policy adviser George Papadopoulos were not truthful with the FBI. And Trump's former campaign manager Paul Manafort, together with another former Trump campaign official, was indicted on charges including alleged money laundering. Manafort's lawyers claim the money laundering charges were constructed using a " tenuous legal theory ," because authorities don't have enough evidence to charge him for a greater crime. While these charges don't stem from their campaign work, it seems that Manafort's trial might be starting this fall , right in time for midterm elections.

If that wasn't bad enough, last week we learned details of an alleged affair Trump had with porn actress Stormy Daniels. While this new allegation didn't make as big an impact as some expected, this story is not going away anytime soon, as Daniels has just started a promotional tour trying to take advantage of the publicity. Both Daniels and Trump denied the affair in a statement sent by Trump's lawyer.

This "perfect storm" of Trump problems is causing a growing sense that the Republicans are in trouble come November's midterm elections. We saw evidence of that in Alabama last month with the stunning victory of Democrat Doug Jones, making him the first Democrat in 25 years to win a Senate seat in that very red state.

And last week we saw more evidence that a "blue wave" could be coming after a Wisconsin state Senate special election in a district that Trump had won by 17 points in 2016 went to a Democrat by 11 points. Even GOP Wisconsin Gov. Scott Walker raised red flags with his tweet that this "special election win by a Democrat is a wake-up call for Republicans in Wisconsin."

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Although a recent CNN poll shows that Democrats' advantage in the midterm elections is narrowing, they still lead Republicans 49% to 44%.

Given all that, Trump must be wishing he could make yet another bankruptcy filing -- his presidency. But he can't. Nor are there any tax code loopholes or high-priced accountants that can save him this time. For once Trump will have to actually either turn things around or face the consequences. Finally, we will all get to see if Trump is as great a dealmaker as he boasts.