What could be a critically important relationship between the city's newly elected mayor and state lawmakers is off to a rocky start after Mayor-elect LaToya Cantrell showed up at a meeting this week with one of the legislators' former colleagues: ex-con Derrick Shepherd.

Shepherd, a former state senator who served more than a year in federal prison after pleading guilty to money laundering, accompanied Cantrell to a meeting with New Orleans legislators designed to begin building relationships during the five-month transition before she is sworn in.

But any good will the gathering was intended to generate may have been squandered by Cantrell's decision to include the former West Bank lawmaker.

State Sen. Conrad Appel, a Metairie Republican whose district includes parts of New Orleans, confirmed Shepherd was at the meeting, which was held at a local church. He said Shepherd did not take part in the general discussion, in which Cantrell urged cooperation over the coming years, and it was not clear what his role there was.

While Shepherd’s potential role in the Cantrell transition or the new administration remains unclear, several legislators who asked not to be named said they had serious concerns that the mayor-elect would bring someone with his history to such a meeting.

Cantrell spokesman David Winkler-Schmit said by text message Friday that Shepherd “has no defined role or position in the transition.” But he did not immediately respond to questions about why he was at the meeting.

“The mayor-elect has been holding various meetings with community members and is very excited about the future for the city and the transition,” Winkler-Schmit said. “The future is bright as we move forward together as a city.”

Shepherd, a Marrero Democrat, was seen as an up-and-coming politician when he was elected to a state House seat in 2003, and he won a spot in the state Senate during a special election less than two years later.

That was followed by a bid to unseat U.S. Rep. Bill Jefferson, who was already dogged by the corruption allegations that would eventually land him in federal prison. But Shepherd came in third behind Jefferson and then-state Rep. Karen Carter Peterson — now a state senator and head of the state Democratic Party.

That race would play a role in Shepherd’s own downfall, after Jefferson connected him with a bond broker who needed a partner in a money laundering scheme involving bogus bonds.

Shepherd moved about $141,000 through his law firm as part of the deal, keeping about $65,000 for himself and his campaign account, according to a federal indictment. 

Shepherd was originally charged with multiple crimes. But in a plea deal with prosecutors, he pleaded guilty to just one count of conspiracy to commit money laundering and resigned from the Legislature in late 2008.

He was sentenced to more than three years in prison in February 2010, serving time both behind bars and in a halfway house before being released to federal probation in March 2012.

His early release was, in part, due to cooperation with federal investigators on other cases, according to documents Shepherd filed with the Louisiana Supreme Court as it considered whether to permanently disbar him. 

He was disbarred, and it is not clear how he has made a living since his release. 

The former lawmaker also has faced multiple allegations of domestic violence, including accusations that he attacked a jilted lover in 2008 and left her bruised after breaking down her door in the middle of the night. She claimed it was the third time he had attacked her.

Allegations of domestic violence could be particularly toxic for relations with the New Orleans delegation, some of whose members have led the campaign to root out sexual harassment and abuse in the Legislature.

While most politicians with such a history would have long ago retreated from the limelight, Shepherd mounted a short-lived attempt at a comeback after his release from prison.

Despite a state constitutional amendment barring felons from the ballot for 15 years after their release, Shepherd signed up to run for his old House seat in 2015. He was disqualified and went on to challenge the constitutionality of that provision, pointing out that the language passed by the voters differed from the wording that had been approved by the Legislature.

In a Pyrrhic victory, Shepherd won the legal case but months after the election had passed without his name appearing on a ballot. State lawmakers have still not put a new version of the amendment before the voters.

Given Shepherd's liabilities, several lawmakers said any association with him showed poor judgment by Cantrell. Any involvement he would have in politics in Baton Rouge could also give lawmakers from elsewhere in the state cause to question or oppose initiatives sought by New Orleans, which already is a frequent target for criticism.

It’s important for an administration to maintain a positive relationship with the city’s legislative delegation in the best of the times in order to try to steer bills through the Capitol, ensure local projects get funding and block provisions that would harm the city.

And building those relationships could be even more critical for Cantrell because many members of the delegation sided with her opponent, Desiree Charbonnet, in the elections this fall. 

Asked earlier this week whether he was seeking or had taken a role in the Cantrell administration, Shepherd said, “I defer all questions to Madam Mayor-elect.”

Follow Jeff Adelson on Twitter, @jadelson.​