I’m having trouble envisioning how.

He hit the ground running on Primary Election Night with an ad that slapped Republican nominee Bruce Rauner for his minimum wage flip, but since then it seems like everything that could go wrong has gone wrong.

Quinn showed tremendous political courage, or stupidity depending on your perspective, by calling for a tax increase with the permanent extension of the 5 percent rate. Then, of course, House Speaker Michael Madigan unceremoniously gave up on it, some say without really trying , as he read the political tea leaves and saw a vote for a tax hike would be bad for maintaining his supermajority.

So now Quinn gets to run for reelection while stumping for a tax increase for the second time in a row. Has there been an Illinois governor who has successfully run twice on a promise of raising taxes? Has there been a governor in any state who has done that?

What else has gone wrong for Quinn? Let’s count:

1. There’s the multiple investigations into the Neighborhood Recovery Initiative after Auditor General Bill Holland essentially confirmed that Quinn’s administration took $55 million and tossed it to the wind just before the 2010 election.
2. There’s also the report that Quinn’s administration at the Illinois Department of Transportation violated patronage hiring rules, making scores of hires that should have been exempt from politics.
3. And now comes word, again from Holland, that the healthcare and family services department paid $12.3 million in Medicaid dollars for services to people who had been dead for years. As in, checks were being issued in 2005 for services for people who had died in 1989. I doubt we’ve heard the last of that one.
4. Quinn failed to get his $500 property tax payments for homeowners along with the income tax increase.
5. Oh and he didn’t get the expansion of the earned income tax credit he’d sought either.
6. Wait, there’s more. With great fanfare, Quinn announced the formation of a transit task force back late last summer after the Metra CEO severance scandal. The task force was led by respected former U.S. Attorney Patrick Fitzgerald and other prominent citizens. They issued an extensive report in late March and it landed with a thud and has nearly disappeared from view, despite Democratic supermajorities in Springfield.

Madigan reportedly wasn’t happy the report offered up more details about his efforts to use Metra as a patronage haven and Rahm Emanuel dissed those who worked on the recommendations and those who supported it as “propeller heads.” I’m not sure what a “propeller head” is, but I gather it wasn’t a compliment.

With Democratic friends like those, who needs enemies like Rauner? Of course, it can be argued Quinn has dug the hole he finds himself in nearly all on his own.

The question becomes can he scratch his way out? What is most bewildering is that Quinn hasn’t responded much or well to any of this. He’s hired a good campaign team, including strategists who helped Bill De Blasio to victory in New York.

But while Camp Rauner issues multiple attacks daily about this scandal or that tied to Quinn or “Quinnochio,” as they’ve annoyingly dubbed him, Quinn’s team only recently began using running mate Paul Vallas for some counter attacking.

It took them until last week to put out a clever You Tube video about the epic-length silence from Rauner about solutions to the state’s epic financial mess. (Is it due time yet, Mr. Rauner?)

This isn’t brain surgery. Rauner has been working to soften his anti-union bona fides and using his wife to try to expand his appeal with women, independents and Democrats while also strongly suggesting Quinn is as corrupt as his former ticket mate Rod Blagojevich.

Where’s the rapid response the Democrats minted back in the days of the first Clinton presidential campaign?

It might be that Quinn already has let his own missteps and Rauner’s money define him.

Democrats always say Quinn never should be counted out. He’s a strong closer, they say. And he has proven that before.  He’s got a whole lot of proving to do again in the next five months.

NEXT ARTICLE: Is a more experienced state representative a more effective state representative?

1. We need a balanced budget or it’ll cost all of us
2. Where did Illinois rank on this year’s best and worst states for business lists?
3. No salary streamlining for superintendents at Cook County school districts
4. Stop increased spending and permanent tax increase
5. Civic Federation: Don’t let tax increase expire; start taxing retirees

Madeleine Doubek is Reboot’s chief operating officer. She previously managed the Daily Herald newsroom. An award-winning journalist, Doubek served as the Daily Herald’s political writer and editor and led the paper’s project and investigative work. She believes in more of us taking charge of our state government. Read Doubek’s personal take on why she’s rebooting. You can find Reboot on Facebook  and on Twitter @rebootillinois.