A 28-year-old Hoboken political operative has admitted participating in a cash-for-votes scheme, becoming the fifth person implicated in a widening federal investigation that has rocked the city’s political world.

Matt Calicchio pleaded guilty in federal court on Tuesday to using mail to promote voter bribery in the 2013 and 2015 city elections, U.S. Attorney Craig Carpenito announced in a statement. The scheme centered around mail-in ballots.

The guilty plea from Calicchio, a Democrat who has been involved in Hoboken politics for more than a decade, is potentially bad news for developer Frank “Pupie” Raia, who is one of the five people federal prosecutors have charged in their probe. Calicchio said Raia, whose trial is scheduled to begin in June, directed him in 2013 to promise residents $50 for their votes, prosecutors say.

Calicchio also admitted doing the same in 2015 for an unnamed candidate for Hoboken City Council, prosecutors say.

“The candidate told Calicchio that the candidate wanted to win at all costs, and the candidate further indicated that everyone who voted by mail would get paid,” reads Calicchio’s charging document.

There is a second unnamed 2015 council candidate referenced in the document. Prosecutors say the first directed Calicchio to arrange payments for voters, while the payments were drawn from the second candidate’s campaign account. The only identifying information for this second candidate is prosecutors say they were chair of their own campaign account.

All six of the city’s ward council seats were up for grabs that year, and 13 candidates were on the ballot. Their campaign finance documents show most of them did not declare who chaired their account.

The election that year was largely a battle between the “new Hoboken” associated with then-Mayor Dawn Zimmer and the city’s “old guard.” Calicchio campaigned for the latter.

“Mr. Calicchio went into court today and accepted responsibility for his actions," said his attorney, Michael P. Koribanics. “He’s ready to move on with his life.”

Here’s how the scheme worked, according to prosecutors: operatives like Calicchio agreed to pay voters $50 if they applied for mail-in ballots and used them to vote as directed. The voters would receive the money after the election.

Prosecutors allege the 2013 operation was overseen by Raia, who has pleaded not guilty. Raia, a Democrat, was a council candidate in the city’s nonpartisan municipal race that year and supported a referendum that would have weakened rent-control laws. He and the referendum lost.

Roman Brice, who blogs at Mile Square View, posted a picture in 2013 of people lined up outside Raia’s social club the night after that year’s election. He quoted one woman who told him she had been paid to vote.

Calicchio, who is facing a maximum of five years in jail and a $250,000 fine, is the second person to admit guilt in this investigation. In November, Lizaida Camis pleaded guilty to conspiracy to use the mail to promote a voter bribery scheme in 2013.

Even as a teen Calicchio was involved in Hoboken’s rough and often bizarre political world. In 2007, Calicchio claimed to have snapped photos of Zimmer, then a council candidate, not cleaning up after her dog on a city sidewalk. He said when he took that photo, Zimmer grabbed his wrist and tried to take his camera. Zimmer, who was later elected to the council and then mayor, denied all of it.

“The cash-for-votes scheme as outlined by the U.S. Attorney’s office is an unfortunate reminder that corruption and dark special interests still play an outsized role in our municipal elections,” Mayor Ravi Bhalla said in a statement.

State Sen. Sam Thompson, R-Old Bridge, issued a statement Tuesday tying the latest development in this case to his legislation (S-3184) that would increase penalties for people who commit various types of voter fraud, including someone who solicits a violation of election law.

“Our elections and our very democracy will continue to be undermined until we implement better safeguards and deterrents, including stronger penalties like those I have proposed, to combat this type of voter fraud," he said.

Terrence T. McDonald may be reached at tmcdonald@jjournal.com. Follow him on Twitter @terrencemcd. Find The Jersey Journal on Facebook.