US Attorney Carmen M. Ortiz arrived at her post in 2009 to find three big-name politicians indicted and awaiting trial. It was her job to oversee the prosecution of former state Senator Dianne Wilkerson, City Councilor Charles Turner, and former House Speaker Salvatore F. DiMasi — all within her first two years in office.
Seven years later, as Ortiz nears the traditional end of term as the state’s top federal prosecutor, she has one last big investigation ahead of her, and it requires a pivotal decision: how to handle the matter of Mayor Martin J. Walsh as part of an ongoing probe of union strong-arm tactics.
And that decision could be the diciest yet, involving a very popular sitting mayor — with whom she already has a somewhat testy relationship — and his work as a labor leader before taking office.
It would also mark the first time she herself has put a high-ranking public official in the crosshairs. The high-profile cases early in her tenure were launched by her predecessors.
Legal and political analysts say they do not believe Ortiz would hesitate to pursue a criminal investigation against Walsh or anyone else involved in union wrongdoing, but they also pointed to the challenge she faces in determining whether the union strong-arming in question is a crime or a constitutionally protected right.
“Her people will run the course, follow every lead,” said Thomas Dwyer, a veteran defense lawyer and former prosecutor in Boston, who said he knows Ortiz personally. “It’s hard for a US attorney to say, ‘I don’t want to do this because it’s the mayor.’ ”
But, he added: “If you’re the mayor of Boston, you get more of a detailed review than if you were not. She would not return it, she would not approve it, unless there was absolutely no reasonable doubt — the highest standard to get for an indictment.”
Ortiz has overseen some of the most high-profile cases in recent memory, including the prosecution of James “Whitey” Bulger and Boston Marathon bomber Dzhokhar Tsarnaev, but she has also balked at charging high-profile figures such as House Speaker Robert DeLeo, who her own prosecutors have called a coconspirator in a state hiring scandal. DeLeo has denied any wrongdoing.
Christina DiIorio-Sterling, a spokeswoman for Ortiz, would not comment for this story and would not confirm or deny a Walsh investigation.
The Globe reported Sunday that federal investigators are conducting a sweeping probe into union labor tactics, and that Walsh’s work as a labor leader before taking office in 2014 has been drawn into the investigation.
At issue in the investigation is whether labor officials threatened the projects of developers and business people who hired nonunion workers, the Globe reported.
Walsh apparently became drawn into the probe through a 2012 wiretap on which he was recorded saying he had told a development company it would face permitting problems on a planned Boston high-rise unless it used union labor at another project in Somerville, according to people familiar with the tapes.
Walsh has denied having any such conversation and said he has not been contacted by government investigators or appeared before a grand jury regarding his work as a labor leader.
In recent years, three former Teamsters have been convicted in federal court of extortion based on similar allegations. A fourth was acquitted.
In a separate case in September, prosecutors charged five Teamsters with extortion for allegedly harassing the nonunion production crew for the “Top Chef” television show during filming in Milton. The Teamsters allegedly chest-bumped members of the production crew and slashed their tires.
In that case, Ortiz’s office directly tied the Walsh administration to the alleged wrongdoing when it stated in the indictment that a City Hall worker warned several Boston restaurant owners that the union would picket outside their establishments if they hosted the show there. The restaurants ultimately turned the “Top Chef” crew away.
The City Hall worker, Kenneth Brissette, was not charged, although an independent investigator hired by the city said he found a concerted effort by the administration to preserve its relationship with local unions.
Ortiz’s office had been at odds with the Walsh administration at least one other time. In July 2015, an assistant US attorney blasted the city in court documents for listing rumors about misconduct by retired State Police officers to support what it called a frivolous lawsuit against the state Gaming Commission over a proposed casino in Everett. The prosecutor said in a sharply worded court filing that the city made the claims “without a shred of evidence” and despite being told by investigators that the incident involving the retired State Police officers did not happen.
The city’s lawsuit was later dismissed.
Ortiz’ and Walsh’s administration have also since collaborated on other projects including public safety efforts in Boston.
Ortiz, who was appointed by President Obama and confirmed to her post in 2009, is a career prosecutor and lawyer who has never been elected to public office. She was reportedly considered by the Democratic Party as a possible candidate for statewide political office at the beginning of her tenure as US attorney, although it is not clear if she herself has ever aspired to elected office.
The decisions to indict Turner, Wilkerson, and DiMasi were made by Ortiz’s Republican predecessors, Michael Sullivan and interim US attorney Michael Loucks.
One of Ortiz’s biggest decisions involved the 2012 indictment of three former state Probation Department officials on fraud charges, leading to one of the most high-profile federal trials in recent years. A jury found that the probation officials rigged a state hiring process that favored job applicants who were sponsored by the politically connected, including high-profile state representatives and senators.
A veteran prosecutor also tied House Speaker Robert DeLeo to parts of the alleged scheme, but DeLeo was never indicted. He has denied any wrongdoing.
Ortiz was criticized at the time for letting a prosecutor call DeLeo a coconspirator in a criminal fraud case without indicting him. She said at the time that her decision not to indict DeLeo was based on a review of the evidence.
The extent of the current federal investigation into union strong-arming, and Walsh’s possible involvement, remains unknown. But legal analysts said that Ortiz will have to comb through the evidence and set a high burden of proof in determining whether the union strong-arming being alleged constitutes a crime.
While several Teamsters have been convicted in recent years, local unions have mounted aggressive legal challenges and continue to defend their rights to protest and picket, saying that advocacy should not be confused with extortion.
Boston College law professor Robert M. Bloom, a former prosecutor, agreed that Ortiz should let the evidence dictate whether any charges should be filed, saying investigators would have to determine whether any advocacy by a union member crossed the line into an actual threat that could be carried out.
“The type of definition I would look for is whether someone is in a public position to actually say yea or nay on one of these things,” Bloom said. “It’s not just a threat. You’re saying you better do this or you get nothing.”
Sullivan said the end of Ortiz’s term should have no bearing on her decision. Sullivan decried the publicity about the investigation, saying it unfairly taints Walsh and could influence Ortiz.
He added, however, that Ortiz would have to put any politics aside in reviewing the evidence, both party affiliations and political aspirations.
“The decision should be purely based on the evidence itself,” he said. “You want the prosecution to be beyond criticism, for nobody to ever [be able to] suggest that the motivation was ever political in nature.”Valencia can be reached at MValencia@globe.com. Follow him on Twitter @MiltonValencia