Management?

He's chaired the Water Supply Board. He started a successful small business. He's overseen winning issue referendum campaigns.

Smiley's shown he can manage projects and has keen business instincts.  However, overseeing thousands of municipal employees -- and union contracts -- is on a whole other level of oversight.

Can he prove to voters he can handle the jump and prove he has what it takes to be Mayor?

City Ties?

He's the candidate least rooted in the state's capital city, but made up for lost time upon arriving in Providence by becoming a highly connected lobbyist, fundraiser, and some say, outsider-turned-insider.

Will Smiley's political opportunism clash with opponents who have risen through the ranks in Rhode Island?  Potential GOP opponent Daniel Harrop graduated from Brown University before Smiley was even born. 

Relatable?

By all accounts, Smiley's a wonk.  Unabashedly bookish, Smiley humorously played up his dry, erudite persona in his Wes Anderson-styled commercial that received gushing praise in national political circles.

But outside of appealing to his wheelhouse on the East Side Providence, does this speak to the working class resident, the old Italians on Federal Hill, or the culturally diverse South Side? 

Smiley has been a face at nearly every community event around the city since hitting the trail. Will these inroads and introductions be enough to push him over top at the voting booth?

Cianci?

The entrance of former Mayor Vincent "Buddy" Cianci into the race has been the X factor in everyone's campaign since he jumped in for a third go at the post.

By all accounts, Smiley has been the most active on taking on the two-time Mayor -- and convicted felon-- on his record.  Challenging him to a debate, Cianci took the bait and said only after the primary -- and suggested Smiley's deceased father-in-law's establishment, the Foxy Lady, as a location, which Smiley hit back at in turn. 

Will Smiley win the battle of new Providence versus old Providence?  The debate scuffle was sure to be just the first as Smiley has shown he'll go hard at the former rough and tumble Mayor, who will in turn point to his own record turning Providence around, and then ask for Smiley to do the same.

Adrain?

Former Democratic opponent turned potential Independent adversary should Smiley make it through the primary, Lorne Adrain, with his East Side connections and successful business background, presents a foil to Smiley in the effort to with the "ethical reformer" vote. 

Should Smiley eventually face Cianci, Adrain, and the GOP's Harrop, Smiley would have to contend with an "Anybody But Cianci" battle between him, Adrain, and Harrop.  Can he put together the base needed to do so?