'I may have murdered my girlfriend': The story behind Samantha Woll's ex-boyfriend

Two weeks after a beloved synagogue leader was found murdered outside her Detroit townhouse, her ex-boyfriend made a frantic 911 call after taking four hits of marijuana from a vape pen and doubling the dose of his new antidepressant.

"I think I may be a danger to others," the ex-boyfriend told the 911 operator, sobbing uncontrollably and hyperventilating as he spoke from his car in a parking lot. "What have I done? ... I know I'm in big trouble."

Samantha Woll case verdict:Defendant not guilty on first degree murder charge

Within minutes, police would arrive and the distraught man would continue spiraling.

"I'm having a panic attack. I'm convinced that I may have murdered my girlfriend and I don't remember it," the ex-boyfriend told an officer. "I have the motive and the opportunity. I may be trying to outsmart people."

This 911 call may be some of what jurors in the Samantha Woll murder trial struggled with as they delivered a mixed verdict in a complex and emotional case that devastated the metro Detroit Jewish community and her still-grieving family — which may have to relive the courtroom trauma all over again.

On Friday, after five days of deliberations, the jury acquitted 29-year-old Michael Jackson-Bolanos of first-degree murder, convicted him of lying to police, but deadlocked on two other charges: felony murder and home invasion. That means he may face a retrial on those two charges, though the prosecutor's office has a week to make that decision.

'Justice for Samantha has not been served'

For Woll's family, the jury's decision came as an emotional blow as they are convinced that Jackson-Bolanos killed their daughter, and needs to pay for it. As the family stressed in a statement Thursday: "It pains us that justice for Samantha has not been served."

Jurors left the courthouse Thursday without talking to reporters — just as Wayne County Circuit Judge Margaret Van Houten had encouraged.

The defense, meanwhile, also is frustrated, as it maintains that Jackson-Bolanos is not guilty and should have been cleared of all charges — especially given the reasonable doubt that it raised at trial. Specifically, the defense zeroed in on one key player it maintains raises the most reasonable doubt in this case: Woll's ex-boyfriend.

In a case that pits one mans story against another's, here is how police and prosecutors built their case against one man, and allowed another one to go:

Ex-boyfriend gets immunity

Jackson-Bolanos, a habitual offender who says he stumbled across Woll's body while looking for cars to steal from, was charged with fatally stabbing Woll during an alleged home invasion in the fall of 2023. Her blood was found on his coat sleeve and backpack, and cellphone data and video footage placed him near Woll's townhouse in Detroit's historic Lafayette Park neighborhood during the time frame police believe she was murdered.

According to police, Jackson-Bolanos was the only one spotted near the crime scene that night, and he admitted to being there and touching Woll's body, but only after lying more than 40 times about his actions that night.

In a rare move, Jackson-Bolanos took the stand in his own defense, telling jurors that he was in the "wrong place at the wrong time," and that he had nothing to do with Woll's murder. He testified that while out casing cars, he saw Woll's body on the ground, checked for a pulse, then fled when he realized she was dead, fearing he would be blamed for her death.

The ex-boyfriend also testified at trial and maintained that he had nothing to do with Woll's death — though he was granted immunity, which means he can't be prosecuted for anything he said on the witness stand.

The defense emphasized this point during closing arguments as it sought to plant seeds of reasonable doubt in the minds of the jurors, who spent four weeks listening to testimony from more than four dozen witnesses, including police, forensic experts, crime scene analysts, a home security expert, neighbors and people who knew Woll personally.

The prosecution is adamant that Jackson-Bolanos is the killer, maintaining his motive for lying to the police was the same motive for killing Woll: He was a repeat offender who knew that he was "going to go down for a long time" if he got caught committing any new crime.

But the defense insists Jackson-Bolanos is innocent, arguing Woll's brutal murder was a "crime of passion" carried out by someone who knew her; that police ignored other potential suspects and conducted a shoddy investigation; and that there is no evidence that shows his client was ever in Woll's apartment.

According to trial testimony, surveillance footage, cellphone data and DNA evidence, here is how the prosecution built its case against Jackson-Bolanos, and why the still-grieving Woll family believes he's the killer. As the family stated following his 2023 arrest: "We firmly believe that they have successfully solved this senseless crime."

Murdered after a wedding

It was just after midnight on Oct. 21, 2023, when Woll was driving home on Interstate 94 from a wedding. Police said she left the wedding alone, and appeared to be her normal, happy, joyful self, according to other wedding guests.

She arrived at her townhouse around 12:30 a.m. About a half hour later, her security system alerted that the front door had been left open and there was no evidence that it was ever closed.

At 1:02 a.m., Woll sent a text message to a friend and her phone stayed on for almost a half hour. At 1:35 a.m., her phone unlocked again and her Netflix app was up and running.

Police said they believe Woll fell asleep on her couch when, at 4:20 a.m., a sensor captured motion in her living room. Police said they believe this is when Woll was murdered. Her security system went idle at 4:22 a.m. There was no more movement. Police would later find signs of a struggle: Pillows on the floor. Blood stains underneath. A fruit bowl knocked over.

Four minutes after motion was detected in her living room, Jackson-Bolanos was seen on video a quarter-mile away from Woll's home, crossing the Monroe Street bridge over I-375. The defense argued there was no way he could have killed her and made it to the bridge that quickly. A detective countered that it was possible, as he walked, jogged and sprinted the route, and presented his findings to the jury: It took him just over a minute sprinting; 1 minute and 41 seconds jogging; and 3½ minutes briskly walking.

At 6:30 a.m. on Oct. 21, a neighbor who was out walking their dog found Woll's body on the sidewalk outside her home. A trail of blood led from her walkway to the sidewalk. She had been stabbed eight times in the head and neck.

According to trial testimony, an unidentified person was captured on video running in the area about 1:25 a.m. that night. Police were not able to identify who the person was and ruled the individual out as a suspect because Woll's phone showed activity through 1:35 a.m.

Police arrest first suspect: the ex-boyfriend

Weeks passed before police announced a suspect — and it wasn't Jackson-Bolanos.

Initially, there was concern that this was a hate crime as Woll was murdered exactly two weeks after Hamas attacked Israel, sparking a deadly war in the region and an increase in antisemitism across the United States. Police, though, said they found no evidence of antisemitism in the Woll case. Rather, they got a tip about someone she knew.

On Nov. 8, 2023, two and a half weeks after Woll's death, police announced they had a suspect in custody. They did not disclose who the suspect was, though multiple sources said it was someone with close ties to Woll who had attended her funeral.

Two days later, the suspect was released. Police offered no details, though we now know who the person was, and how he landed on law enforcement's radar.

It was Woll's ex-boyfriend, 41-year-old Detroiter Jeffrey Herbstman, who, just weeks after Woll's murder, made the shocking 911 call during what he described as a full-blown panic attack, telling police: "I may have murdered my girlfriend."

'I had convinced myself that I had killed Samantha Woll'

According to police body cam footage, a videotaped interrogation of Herbstman and Herbstman's own testimony, here is how he became suspect No. 1:

On Nov. 7, 2023, Herbstman, a data scientist, was in Kalamazoo for work when a wave of panic came over him. He was in his hotel room, he said, and had just taken his second dose of a new antidepressant, along with some hits of marijuana off his vape pen.

His thoughts started racing. He couldn't breathe. He packed his belongings, went to his car and called 911.

"I was very fearful of what I could have possibly done," Herbstman testified at trial as he sought to explain to the jury his frantic 911 call.

"Due to the adverse effects of my medication, I had convinced myself that I had killed Samantha Woll," a soft-spoken Herbstman testified at trial, showing little to no emotion as he watched the video replay of his interaction with Kalamazoo police in the hotel parking lot.

He is heard telling police things like: "I'm in trouble" and "I don't remember. I don't remember anything."

Later that night in a police interrogation room, he is seen on video footage rocking back and forth, frantically stating: "I'm going to lose my job. I'm going to lose everything."

Ex-boyfriend: I was home alone on night of killing

Jurors also saw video of Herbstman calling his parents from the police station, asking his mom if she could "please contact that attorney for me." His mom never asked him why he was at the police station, or how he was doing, but she did ask: "Are they holding you?"

During his testimony in court, the prosecutor asked Herbstman to explain what he meant in his 911 call by saying "I have a motive" and "I may be trying to outsmart people."

Herbstman answered: "People may have thought I had a motive because we had broken up." He also expressed concern about his not having an alibi on the night Woll was killed. According to his testimony, he had gone to synagogue the night before Woll died, went home, listened to a podcast between 8 p.m.-10 p.m., and put on a record before going to bed.

Herbstman said he was alone that night and did not learn about Woll's death until the following afternoon when the synagogue had alerted him and others about her death. He said he immediately turned to news media reports to learn more.

According to the prosecution, police thoroughly investigated Herbstman — scouring his house, vehicle, phone records, scooter and Uber and Lyft records — but found nothing that tied him to Woll's murder. It said his cellphone data placed him at home that night, though the defense argued he could have intentionally left his cellphone at home to avoid being traced.

Still, the prosecution maintains his confession was false, and that he provided no details about her death, so police let him go.

Another two months would pass before police arrested Jackson-Bolanos. They had tracked his movements across the city of Detroit in the early morning hours of Oct. 21, where surveillance video taken from various locations showed him in all black, walking from his girlfriend's apartment in Midtown to Woll’s neighborhood and back, at times wearing surgical gloves and a mask. Police said they had footage of Jackson-Bolanos from 18 locations and 35 video systems that morning, and a matching timeline of cellphone pings that helped them connect the dots.

In December 2023, after police picked up Jackson-Bolanos during a traffic stop in Macomb County, the Wayne County Prosecutor's Office announced murder charges against him in connection with Woll's death.

Defense grills ex-boyfriend: 'She rejected you'

From the get-go, defense attorney Brian Brown lambasted the prosecution for bringing the case, maintaining police arrested the wrong man for Woll's killing.

"We're not saying he's an angel. But he's not a murderer," Brown said in his closing argument, alleging police did not look closely enough at other potential suspects, including another love interest of Woll's, and a friend who allegedly explained to someone how he would hypothetically evade police if he were the one who killed Woll.

Brown, though, focused primarily on Herbstman and grilled him extensively during cross-examination about his relationship with Woll. Brown sought to portray him as a jilted ex-boyfriend who couldn't deal with rejection.

According to Herbstman, he and Woll dated for about a year before she ended things last July. He said she wanted more than he was giving her, such as physical affection.

"I blame myself," he testified.

"Did you change?" Brown asked him.

"I tried," Herbstman said. "I tried to call her more. She wanted more physical touching, so I tried that. I bought her flowers. I apologized."

They got back together, he said, but she broke up with him again.

Brown dug in, telling him: "She still rejected you, didn't she?"

"I think rejection is an extreme (word)" Herbstman responded.

Brown quipped: "She didn't embrace you in her arms and y'all lived happily ever after. That didn't happen, did it?"

Herbstman said he understood why the relationship didn't work and that he wrote Woll a text that said, "I understand."

Defense: 'Do you always just make things up that didn't happen?'

Brown also grilled Herbstman about his claims that he was "delusional" when he convinced himself that he killed Woll.

"Do you always just make things up that didn't happen?" Brown asked.

"No," Herbstman responded.

"So, you're saying this is the only time that you can remember that you made up something?" Brown continued.

Herbstman said it was the only time that he recalled having an adverse reaction to medication.

"Did that medication make you visualize something in your mind that happened?" Brown asked.

"No," he answered.

'Are you familiar with repressed memory?'

Brown then posed this theory.

"Are you familiar with repressed memory ... or blocking out details of a traumatic event?" Brown asked as he pushed Herbstman to explain whether he tried digging deeper to figure out why he blamed himself for Woll's death.

"You didn't try to get to the truth of the matter, and say, 'OK, maybe I had a repression of a traumatic event?'" Brown asked. "You never tried to figure that out in this situation?"

Herbstman said he never tried.

"It was more convenient for you — of course — to take the 'It's a delusion' road," said Brown, who also questioned the man's claims that this was his first adverse reaction to his new medication.

"You went from no side effects to convincing yourself of doing a murder?" Brown asked.

"Yes," Herbstman answered, though he stressed that he never killed anyone and that his thoughts about doing so were based on drug-induced delusions, not fact.

"Are you responsible for Samantha's death in any way?" Assistant Wayne County Prosecutor Ryan Elsey asked Herbstman during trial.

"No," he answered.

'Don't believe him'

The jury would hear from another 30-plus witnesses before Jackson-Bolanos took the stand, admitting he initially lied to police about not seeing or touching Woll's body the night he was out casing cars for things to steal. But he only did so, he said, because he feared getting blamed for her death.

"When I realized she was dead, I wanted nothing to do with the entire situation," he testified, noting: "I’m a Black guy in the middle of the night, breaking into cars, and I found myself standing in front of a dead white woman. It doesn’t look good at all."

Hogwash, the prosecution countered during closing arguments, calling Jackson-Bolanos a chronic liar and imploring the jury to convict him.

"There are simply too many coincidences to suggest that anyone other than the defendant killed her," Elsey argued to the jury, saying the defendant has lied repeatedly.

"Don't believe him," Elsey told the jury. “He got caught in a lie. ... He sat in that witness chair and lied to you. That’s all he did. He lied and lied and lied.”

Contact Tresa Baldas: tbaldas@freepress.com