HOW A RAPE CASE EXPOSED A TANGLED WEB OF DYSFUNCTION
Conflict of interest sparks infighting between City Hall, FPC that upends police chief search
Jane Doe wasn’t the type who forgot to pick up her kids. But on Nov. 4, 2014, her mother got a call from their school: Doe had never arrived. She wasn’t answering her phone. Around 7 p.m., with panic setting in, a group that included her mother, her best friend and the father of her children showed up at Doe’s house. Her mom called the Milwaukee police. The others broke a window and forced their way inside. It didn’t take long for the group to find Doe: She was in bed, eyes closed, hands pressed together against her cheek. She woke to her best friend’s shouts: “What are you doing? You didn’t pick up your kids!” Doe told police she had fallen asleep.
She didn’t tell them she felt as if everything was moving in slow motion — and she’d felt that way since the man she’d been seeing, Kalan Haywood Sr., made her a drink early that afternoon. She didn’t tell them that after a few sips of that drink she’d lost consciousness.
The next morning, she got the shakes at work and couldn’t focus. Pain wracked her neck and throat.
When she called Haywood to ask him what happened, she recalled, he told her they had sex, then he urinated in her mouth and recorded it.
Doe didn’t remember any of that and later told police she never would have consented to such a thing. Haywood had respected her boundaries during their earlier sexual encounters, she said, but this time, she believed he had crossed them.
She started making excuses to avoid seeing Haywood but continued to text him for about a week, she said later, buying time to change the locks on her house and car. She never met up with him again.
After three or four days, Doe told a friend what happened and the two of them went to the sexual assault treatment center at Aurora Sinai Medical Center. Health care workers didn’t do a rape kit, Doe later said, but they took photos of severe bruising on her thighs and gave her medication to prevent sexually transmitted diseases.
She stuffed her torn bra and the polka-dot sheets from her bed into bags and left them in the corner of her room.
The Milwaukee Journal Sentinel does not publish the names of people who report being sexually assaulted unless they agree. In this case, the woman did not. In a lawsuit filed against the Police Department and the city last year, she used the pseudonym Jane Doe.
In 2019, Doe reported to police that Haywood, a prominent real estate developer, had raped and possibly drugged her. He denies wrongdoing and has not been arrested or charged; her allegations remain under investigation by law enforcement and prosecutors.
Doe’s lawsuit, which argued that the Milwaukee Police Department violated her rights as a crime victim by repeatedly failing to notify her about important developments in the investigation, was settled earlier this year. As a result, the state Department of Justice has taken over the case. The settlement also creates a legal pathway for crime victims throughout Wisconsin to ensure their rights are protected.
On the surface, there appear to be several reasons why Doe’s case stalled, including the five years she waited to report the incident to police.
But a Journal Sentinel investigation uncovered problems that go far beyond a mishandled rape allegation — problems that affect the lives of Milwaukee residents who have nothing to do with Doe’s case.
The man Doe accused is influential, the beneficiary of millions of dollars in taxpayer-funded city loans for development projects. One of his attorneys was a member of the powerful Fire and Police Commission, which has the final say on which police officers should be promoted and disciplined — including those in charge of investigating Doe’s case. The conflict of interest sparked infighting among commissioners and public officials that has upended Milwaukee’s search for a new police chief.
This tangled web of dysfunction — which has the potential for huge legal costs to taxpayers — is playing out amid Milwaukee’s history of complicated racial dynamics. Decisions have been made, and alliances formed, with gaining or keeping power taking priority over protecting the best interests of the city and its residents. Meanwhile, Doe waits for justice. Through her attorneys, Doe declined to be interviewed for this story. Information about her case comes from police reports and video, Fire and Police Commission records and her lawsuit.
“It’s important to Jane Doe, particularly as a Black woman in Milwaukee, that the people in positions of authority acknowledge, reflect on, and learn from her experience,” one of her attorneys, Rachel Sattler, said after filing the suit in October.
“Up until now, and throughout this process, she has been repeatedly retraumatized and disempowered.”
Years of conflict among leaders
Much of the fallout that would eventually surround Doe’s case was rooted in the racial tension that marked Edward Flynn’s decade as police chief.
During his tenure, the Police Department became embroiled in a lawsuit alleging racist stop-and-frisk practices. And it was left reeling after a draft of a federal Department of Justice report, which revealed deep mistrust between police and people of color, was leaked to the Journal Sentinel.
Flynn was a divisive figure even before he got the job in 2008. Two consultants recommended him after four finalists — including a Black woman and a Latino man already on the force — had been named, leading some in the city to believe the fix was in.
Flynn was only the second outsider to be chosen as chief in the department’s 153-year history — a history characterized by allegations of racism cemented in the 1960s under Chief Harold Breier.
Brash and outspoken, Flynn used data to guide his decisions. He favored hot-spot policing, which involves moving officers into high-crime areas, where they try to restore order by pulling over cars and stopping pedestrians.
Flynn, who is white, chafed at allegations of racially biased policing. Instead of acknowledging that possibility, he insisted racial disparities were the result of the city’s demographics. To bolster his position, he produced maps showing that high-crime areas correspond with poverty, segregation and other social ills.
Flynn’s time in Milwaukee came to an abrupt end after a high-profile clash with the Fire and Police Commission, which, in addition to choosing the chief and overseeing promotions and discipline, signs off on department policies and investigates complaints from the public. Its civilian board members are part-time, appointed by the mayor and approved by the Common Council.
Long-running discord between Flynn and commissioners came to a head when they ordered him to change a policy he’d put in place to limit highspeed chases, threatening to fire him if he didn’t. Flynn, who had cut back pursuits because of the risk they posed to bystanders, ultimately changed the rule. But it wasn’t enough to salvage his broken relationship with the commission or the Common Council.
Flynn still had one ally at City Hall. Mayor Tom Barrett stood at Flynn’s side when he announced he would retire with more than two years left in his third term as chief.
Flynn didn’t leave quietly. During his final days on the job, he traded misconduct allegations with MaryNell Regan, whom Barrett had appointed as the Fire and Police Commission’s executive director three years earlier.
Flynn said Regan tried to interfere with the internal investigation of a police captain who was a friend of hers. Regan said Flynn abused his police powers by accusing her of a conflict of interest and shifting the investigation’s focus to her.
Although Regan wasn’t a voting member of the Fire and Police Commission, her position in Barrett’s cabinet was an important one. As chief administrator over the commission’s operations, she advised and guided its members behind the scenes. She also supervised the full-time city staff tasked with carrying out their mandates.
All the while, the chair of the commission was Steven DeVougas, who had praised Regan for helping the group gain independence from the mayor. As a result of his post, DeVougas had the authority to help hasten Flynn’s departure. But he had no say in Regan’s future.
Two months after Flynn retired, Barrett’s chief of staff told Regan the mayor wanted to take the commission “in a different direction” and she resigned.
Regan had lasted much longer in the job than either of the next two people Barrett appointed. Her departure would prove detrimental, leaving the Fire and Police Commission barely able to function.
It also marked the first fissure in the relationship between DeVougas and the mayor, who appointed him to the commission in 2013.
Black and then 30 years old, DeVougas brought additional diversity to the board, long criticized for lacking it. After joining the commission, he moved between two large Milwaukee law firms — Hinshaw & Culbertson and Quarles & Brady — before striking out on his own.
He had one primary client: Kalan Haywood Sr., the real estate developer later accused of rape.
DeVougas joined the Haywood Group in July 2017, a fact he never disclosed on city ethics forms even though his smiling staff photo appeared on the developer’s website. That same year, the Milwaukee Business Journal featured DeVougas in its “40 Under 40” series. In a short question-and-answer profile, DeVougas was asked his favorite saying or word.
His answer now seems unsurprising: “Leverage.”
Allegations of racist policing
Near the end of Flynn’s time as chief, on January 26, 2018, Milwaukee police tased the wrong Black man. Sterling Brown was a guard for the Milwaukee Bucks. What’s more, his father was a Chicago-area police officer who had taught his son not to lose his cool with cops.
News of Brown’s arrest — for parking across two handicap spaces outside a Walgreens in the middle of the night — outraged citizens. It illuminated, in stark relief, something Black men in the city had been saying for years: The Police Department had a racism problem.
But this time, because of Brown’s status as an NBA player, city and department leaders would be forced to acknowledge it.
Brown’s arrest was the last in a long line of high-profile incidents that sparked claims of racial profiling and
civil rights violations under Flynn’s leadership.
In 2011, Derek Williams, 22 and Black, died after begging for his life and telling officers he couldn’t breathe while handcuffed in the back of a squad car. No one was disciplined or criminally charged — even after the case was reopened and the medical examiner ruled it a homicide.
In 2013, four white officers were criminally convicted in connection with illegal strip and cavity searches, mostly of Black men, over a five-year period.
Dozens of other officers on the force at the time had broken the law or been involved in other serious misconduct and kept their jobs — including two who would play key roles in the flawed investigation of Jane Doe’s sexual assault case.
The repercussions of both Doe’s case and Sterling Brown’s arrest would come to define the legacy of Alfonso Morales, whom the Fire and Police Commission named interim chief in February 2018.
In a dramatic split decision, DeVougas cast the deciding vote for Morales — 47, Latino and a lifelong Milwaukee cop who had risen to the rank of captain — over a higher-ranked inspector, Michael Brunson.
Morales knew he had to release the body-camera footage of Brown’s arrest eventually, but it was damning, showing a polite Brown confronted by aggressive officers. The new chief needed to get ahead of the storm.
Two months into the job, Morales dispatched Brunson, whom he had quickly promoted to assistant chief, to talk to Brown. Brunson, who is Black, showed Brown a four-minute clip of the body camera recording and apologized.
Although Morales was media-shy, he paid a local public relations firm $8,200 to produce a promotional video.
“If there’s ever an incident where one of our members makes a mistake, unnecessarily escalating a situation, I’m going to be honest and transparent about it,” the chief said in the video.
But given his first chance to keep that promise, Morales failed.
Just 24 hours after releasing the PR video, Morales called a news conference, where he played some of the body camera footage of Brown’s arrest. Then he announced that several officers had
been disciplined because they “acted inappropriately.” But he did not name them, nor did he say what they did or what discipline he had handed down.
Stunned reporters pressed for details, but the new chief refused to say anything more.
If Morales hoped that would be enough to allow the department to move on, he was wrong.
In June, media outlets, including the Milwaukee Journal Sentinel, obtained additional body camera recordings that showed Officer James Collins placing his foot on Brown’s ankle as the NBA player lay on the ground. Still on the scene later that night, Collins called in to request overtime, singing “Money, money, money, money!” before appearing to fall asleep in his squad car.
Later that month, Brown filed a civil rights lawsuit against the city, which included screenshots of racist Facebook posts a cop made about his arrest. In the fall, Morales fired that officer.
Word eventually got out that Morales had suspended the officer who first approached Brown, as well as two sergeants. The chief ordered Collins, who had a history of misconduct allegations, to undergo remedial training.
But in the end, no one was fired or demoted as a result of his actions the night of Brown’s arrest.
Less than a year later, Collins missed a 4-year-old girl when he searched a towed van — leaving her in a city lot overnight in 18-degree weather.
The girl was unharmed. Still, Collins’ involvement in that case, kept secret for 11 months, would become a catalyst for Morales’ own showdown with the Fire and Police Commission.
Trusting the police
On July 23, 2019, five years after Jane Doe’s family found her passed out in her home, she reported Haywood to police for sexual assault.
It’s not unusual for victims to wait to report such a crime — if they do so at all. Decades of research have shown the majority of sexual assault cases are never reported to police. Arrests are rare.
A National Institute of Justice study of nearly 3,000 sexual assault cases found that fewer than one in five resulted in an arrest. An even smaller number led to charges, according to the study, which was released in 2019. Of all the rapes or attempted rapes the researchers
reviewed, fewer than 2% were tried in court; most of the criminal convictions resulted from plea bargains.
One reason is gender bias. The problem is so prevalent that the U.S. Department of Justice has released guidance for how law enforcement agencies should address it.
This bias often takes the form of reliance on stereotypes about women or members of the LGBT community. Police may make assumptions about how victims should act, rather than considering how trauma can shape their responses.
As a result, police may treat domestic violence as a family matter rather than a crime, or interrogate a victim the same way they would a suspect.
Racial bias is also an issue, according to the National Institute of Justice. As a result, survivors of color may be seen as “willing participants in their own victimization.” Police are also more likely to view Black victims as uncooperative than white victims, research has shown. This perception may lead to less thorough investigations and therefore a lower likelihood of the perpetrator being arrested or charged.
In recent years, society has gained a wider understanding of the dynamics of sexual assault involving people who know each other. As one expert recently told the Journal Sentinel: “Delayed reporting is the norm and should be expected.”
Doe told an officer she had another reason.
“She was afraid of retaliation,” the police report says. “She clarified that Haywood is a man of importance in Milwaukee, and is known to associate with high-level political officials, including senators and the mayor. (She) said that there are videos on the internet of Haywood making speeches and shaking hands with these important people.”
Doe decided July 2019 was the right time for her to report Haywood to police, despite her lingering fears.
She didn’t know Haywood also had ties to powerful law enforcement officials, including Morales and DeVougas. She wasn’t aware of Sterling Brown’s arrest or the repercussions it would bring to the highest levels of the Police Department. All she knew was that she finally felt strong enough to come forward.
After speaking with police, Doe met with an assistant district attorney.
Then she waited.