The result: A set of circumstances that have left him highly vulnerable both in his primary and the general election – despite the fact that his district is one of the bluest in the country.
And Cicilline's performance in today's primary will say a lot about his prospects heading into the fall.
The good news for Cicilline is he's had plenty of help. First Democrats in the state legislature made his heavily blue district even bluer, drawing from some of the more Democratic areas in the state's other congressional district, held by Rep. Jim Langevin (D-R.I.), and insulating Cicilline from a challenge from former state police superintendent Brendan Doherty (R).
Then they made clear that they wouldn't tolerate infighting in the primary, and no big-name Democrats stepped forward to challenge Cicilline.
That didn't mean Cicilline got a free ride. Today, he faces a rematch with the second-place finisher from the 2010 primary, businessman Anthony Gemma.
But while a quality candidate might well have beaten Cicilline, Gemma's campaign has been consumed by odd behavior and a lack of funding.
Gemma has scraped together a little more than $300,000 for this campaign, including $150,000 of his own money, which is less than he raised in the open primary in 2010 and doesn't go very far on the East Coast.
Gemma has also accused Cicilline of voter fraud and even pitched his economic plan as one that would be written about in the history books.
"When my Congressional 21st Century Jobs Plan is successful, it will be remembered as the opening engagement in a New Industrial Revolution for the 21st century," he said at one point. (For more comments like this, check out the great Ted Nesi's recap.)
The result: Most think Cicilline will eke out a win today.
"Gemma actually ran a better campaign (in 2010) as far as fundamentals," said Rhode Island Democratic consultant Bill Fischer, who does work for the state party, which has endorsed the incumbent. "This was a lot of tilting at windmills, and a lot of mistakes made, and I don’t think he ever really found his voice. He came across as very erratic."
But it's not clear that Cicilline's win – if it is in fact a win – will be resounding. And many are looking to his margin of victory for clues about his standing in the general election.
Cicilline still has major problems. A Brown University poll this year showed just 15 percent of Rhode Island voters rated him either "excellent" or "good," while 24 percent rated him "fair" and 43 percent rated him "poor."
Even among Democratic primary voters, Cicilline has plenty of work to do. A recent WPRI poll showed 52 percent of registered Democratic voters rated him "fair" or "poor," while 40 percent rated him "good" or "excellent."
That same poll showed Cicilline leading Gemma 43 percent to 31 percent, but in a low-turnout primary, polling tends to be less reliable.
Even if Cicilline does emerge victorious, he's got ground to make up in the general election. A February poll showed Doherty leading by double digits, despite the district's heavily Democratic lean. And the recent poll of the Democratic primary showed most Gemma supporters would vote for Doherty (52 percent) over Cicilline (29 percent).
Not to mention the fact that, during the Democratic contest, Doherty hasn't had to deal with attacks. Thanks to the late primary, Democrats will need to refocus their efforts quickly in a scant eight weeks until Election Day.
"The outcome of that has been a benefit for Doherty," Fischer said. "He’s been kind of off in the corner. He’s kind of had a free ride."
Of course, Fischer noted, that also means Doherty still has work to do in introducing himself.
Even if the GOP wins this year, though, it will be hard for them to hold the seat in future elections. Even when the two national parties have nabbed a seat like this thanks to extraordinary circumstances, it has often flipped right back soon after.
(Recent examples include Republicans Charles Djou and Joseph Cao in heavily Democratic districts in Hawaii and New Orleans, respectively, and Democrats Bobby Bright and Walt Minnick in heavily conservative Alabama and Idaho, respectively. All four won their seats in recent years and just as quickly lost them.)
But a potential Cicilline loss would certainly be a headache for Democrats, and would also serve to elevate Doherty as a potential future statewide (governor?) candidate.
And if that loss somehow comes tonight, it would be an even bigger embarrassment for a party that has worked hard to fortify a former Providence mayor who was once considered a future statewide candidate in his own right.