Keith Ellison and Mike Freeman go back nearly three decades — sparring in courtrooms, praising each other at inaugural ceremonies and examining together how police killings are handled in Minnesota.

Now, two of the state’s biggest legal personalities are again reunited to confront a legal quagmire that could either gild or tarnish their careers: the prosecution of four former Minneapolis police officers involved in the May 25 killing of George Floyd.

For Ellison, the state’s first black and Muslim attorney general, it has also required defending a partnership with a white male prosecutor who lost the trust of many people of color.

“I would hope that if people want us to do something that really has not been done yet, which is to convict a police officer of second-degree murder, that people would not try to prescribe how I do it and who I do it with,” Ellison said in an interview last week. “We’re trying to come up with justice for George Floyd, and for anyone to say you’ve got to do it this way and only with these people seems to me kind of unfair.”

Freeman declined to comment for this article. He has not spoken publicly since May 31, when Ellison took the lead in prosecuting former Minneapolis police officers Derek Chauvin, J. Alexander Kueng, Tou Thao and Thomas Lane. Instead, the former two-time gubernatorial candidate and longtime Hennepin County prosecutor has been silent. Ellison, meanwhile, has become the public face of the prosecution, participating in a battery of national news interviews since the case began.

At the outset, theirs has been a union of necessity: Freeman leads the state’s biggest criminal prosecution unit and last year won the only murder conviction against a Minnesota police officer: Mohamed Noor, who fatally shot Justine Ruszczyk Damond in Minneapolis three years ago.

Ellison, who has a deep history in civil rights activism, enjoys a trust from Minnesota’s black community that Freeman cannot claim.

“They both need each other and, quite frankly, I think that justice requires it in the context of their partnership and working this case together,” said Ramsey County Attorney John Choi, who was the first to charge a Minnesota officer in the death of a civilian when he unsuccessfully prosecuted former St. Anthony Police Officer Jeronimo Yanez in the 2016 killing of Philando Castile in Falcon Heights.

Gov. Tim Walz said he asked Ellison to take over the case upon the urging of Floyd’s family. Ellison faces continuing calls to elevate the murder charges against Chauvin to first degree, which would require proof of premeditation. His partnership with Freeman could also fray Ellison’s support among the same civil rights activists with whom Ellison has marched for decades.

“When you start off praising Mike Freeman, then where is our justice going to come from?” said Spike Moss, a longtime Minneapolis civil rights activist, who said Ellison surprised him in May when he brought Freeman to a meeting that Moss helped arrange with the Rev. Jesse Jackson.

Activists like Moss point out that Noor — the only police officer convicted by Freeman’s office — was a black man who shot a white woman. Many took issue with what they described as Freeman’s boastful tone while highlighting that case when he announced the initial charges against Chauvin: third-degree murder and second-degree manslaughter.

More than 20 years ago, Moss led a protest after a black 16-year-old Minneapolis boy was shot by police and charged with threatening the officers with a pellet gun. Ellison represented the boy and rejected a plea deal before Freeman agreed to drop charges. At the rally, Ellison told a Star Tribune reporter that “police brutality … won’t change unless we’re willing to do something about it.”

In 2015, then a congressman, Ellison flew back to Minneapolis to huddle with protesters enraged at the Minneapolis police killing of Jamar Clark. The case prompted an 18-day encampment at the city’s Fourth Precinct police station. Freeman declined to file charges in that case, citing evidence that the officers involved feared for their lives during a struggle over a gun. Ellison met with Freeman and urged him to stop using secretive grand juries to make charging decisions in police killings. Freeman has since made those calls himself.

Clark’s death was among the many deadly police encounters that weighed on Ellison’s mind as he and Public Safety Commissioner John Harrington convened a working group on the subject last year. Freeman spoke at several public forums and voiced support for giving Ellison’s office authority to lead all of the state’s prosecutions of officers charged with killing civilians.

Earlier this month, the Minnesota County Attorneys Association formally agreed to recommend legislation that would require such cases to be investigated by Ellison’s office. Washington County Attorney Pete Orput said the decision followed a “very, very long and intense discussion.”

Orput gave up jurisdiction in a recent manslaughter case against a sheriff’s deputy in his county to avoid accusations of a conflict of interest. He supports this being standard practice for all police-involved homicides.

“Because there’s some cynicism out there, and I’m not sure it’s not unwarranted,” Orput said.

Ellison has a long record of trying cases, but all of that has come as a defense attorney. He said in an interview that he “probably” won’t personally try the four former Minneapolis officers charged in the death of Floyd. Either way, longtime prosecutors and former attorneys general still say his work on approaching cases from the defense’s perspective could serve him well.

“The interesting thing in this is that … the facts involved in this matter are known — they’re on videotape, for crying out loud,” said Mike Hatch, a former Minnesota attorney general. “So it’s not going to be a great deal of investigation going on to find out what happened. What it’s going to be is a great deal of legal issues that crop up — everything from a change of venue to the difference between second- and third-degree [murder].”

Freeman, 72, is not expected to seek re-election in 2022. He faced swift pressure to charge all four officers in the case after a bystander’s video went viral, showing Chauvin kneeling on Floyd’s neck for nearly eight minutes as he pleaded that he couldn’t breathe.

Freeman’s public comments around the initial charges he filed against Chauvin failed to stem the growing unrest over Floyd’s death. The first criminal complaint was seen as hastily assembled. Critics noted that it misspelled Floyd’s name twice and that it seemed to provide more of an argument against prosecution than in support of charges.

“The charges didn’t fit the crime at all, and any intelligent judge would’ve dismissed it,” said Joe Friedberg, a veteran Minneapolis defense attorney.

Two days after Chauvin’s arrest, Freeman asked Ellison for help and sent out a news release saying the two would jointly be working the case. But the governor caught Freeman off guard later that evening by publicly declaring that it was his call to tap Ellison to take the lead.

It threatened to implode the partnership before it could begin. But the men quickly agreed to work together on what soon became a crucial chapter in the case.

“We just talked a lot, shared ideas, listened to each other, and we got there,” Ellison said.

Less than 48 hours later, Chauvin faced tougher charges of second-degree unintentional murder and the three other former Minneapolis police officers involved in Floyd’s death were jailed and accused of aiding and abetting.

With Freeman standing quietly by his side in front of a room full of national and local press, Ellison reminded all that he would do the talking in this case.

“We have one goal and one goal only: justice for George Floyd,” Ellison said.

As the attorney general opened the news conference up for questions, Freeman left the room without explanation.