The Most Bizarre Things About The Craigslist Killer's Case

On April 10, 2009, a 29-year-old Las Vegas-area sex worker named Trisha Leffler met a man on Craigslist and arranged to rendezvous at a local hotel. When she arrived, a handsome and broad-shouldered young man pointed a gun at her. He bound her wrists, gagged her mouth, and robbed her, according to Boston.com.

Four days later, a "masseuse" named Julissa Brisman made the same arrangement with the same young man. This time a struggle ensued, and Brisman was hit in the head and shot dead. On April 16, a 26-year old sex worker was also bound and robbed at a Vegas Holiday Inn Express, also by a man she met on Craigslist.

It only took the police four days to track down the IP address of their suspect and spot his car on I-95, where he was arrested. His name was Philip Markoff, a 23-year old student at the prestigious Boston University School of Medicine (via Biography). Police found a gun and women's underwear in his apartment. By June, a Grand Jury handed down a seven-count indictment, including murder. But Markoff would never face trial — he was found dead in his cell a year later. It's an almost inexplicable case of a privileged and promising young man exploding his own life in a sudden series of brazen and strangely sloppy crimes. These are the most bizarre details about the Craigslist Killer.

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The Craigslist Killer had everything to lose

Maybe put the strange case of Philip Markoff in the Ted Bundy category: the clean-cut young man you'd least expect was leading a dangerous double life. Markoff has been described as "popular, and involved in student activities including youth court and history club" (via ThoughtCo). He was also, "good-looking and stood out from many boys his age." Six-foot-three with "broad shoulders and a husky frame," Markoff eschewed contact sports but went out for the bowling team and enjoyed golf.

Also like Bundy, Markoff was smart. Bundy was a law student at the University of Puget Sound during the span of his serial slayings in the 1970s. But whereas Bundy skated by on charm, Markoff was academically elite, a member of the National Honor Society in high school. 

The son of a dentist, Markoff grew up in a small town of Sherrill, New York, with a population of just over 3,000. When his parents split, he stayed with his mother, while his brother went with his father to Syracuse. But the divorce didn't seem to throw him off. Those who knew him say he was a "well behaved and a good student," according to ThoughtCo. A neighbor named Dorothy Guider described Markoff as a " sweet" boy and "very intellectual," according to The New York Times. "He was not destructive, no trouble, nothing like that," adding that his family was very proud he'd been accepted to study medicine.

The Craigslist Killer wanted to be a doctor

It's scary to imagine the Craigslist Killer Philip Markoff somehow getting away with his brutal crimes and becoming a practicing physician. But that was his plan.

Markoff graduated from the State University of New York in Albany with a BA in biology, according to Biography. Though Markoff wasn't popular, according to ATI, teachers noticed he was "academically brilliant" and certainly smart enough to get into medical school. And it turns out, this career path isn't unusual for psychopathic personality types. A surgeon is the fifth most popular career choice for people who rate on the psychopathy scale, according to Business Insider. CEO, lawyer, media jobs, and salesperson make up the top four, respectively. 

Psychopaths are characterized by "shallow emotions (in particular reduced fear), stress tolerance, lacking empathy, coldheartedness, lacking guilt, egocentricity, superficial charm, manipulativeness, irresponsibility, impulsivity and antisocial behaviors such as parasitic lifestyle and criminality." But this low level of reaction to stress, of all kinds, including the suffering of others, can actually make for a good surgeon, according to Prospect, translating into the "ability to make objective, clinical decisions divorced from feelings." The last thing you want on the operating table is someone faint at the sight of blood, and Markoff certainly wasn't bothered by such things. That said, Dr. Craigslist Killer would not likely be anyone's primary care provider of choice, given his bedside manner was a decidedly anti-Hippocratic combination of deceit and clumsy violence. 

The Craigslist Killer may have also planned to murder a trans woman

Craigslist killer Philip Markoff was engaged to a woman at the time of his crimes — more on that later — but he may have also been pursuing other sexual lifestyles on the side.

Markoff was using an email address that described him as a "sex addict," according to a Today Show report, via NBC Washington, and was corresponding with graphic emails and photos in a Craigslist group organized for men looking for transsexual connections. He also used the email to register at a BDSM site in the "transvestitism" subgroup and posted about his desires to wear a collar, a leash, and dress in women's clothes, according to Thoughtco

A trans woman may have also nearly become one of Markoff's victims. An anonymous Bostonian told NBC News, via SFist, that she, like his other victims, connected with the murderous med student on Craigslist, under the "males for transsexuals" category. Markoff wrote of himself, "I am a 22 y/o grad student. 6'3", 205, good build, blond/blue eyes ... let me know what else you want to see or know about me." He also included photos that eventually helped police identify him. Fortunately for the anonymous trans woman, she never met up with the burgeoning killer in real life.

The Craigslist Killer's crimes were incredibly sloppy

There's a not wholly unfair assumption about people who get hard science degrees and are then accepted into elite medical schools: that they are really, really smart. And likely Craigslist Killer Philip Markoff was indeed a high IQ individual, but his horrible attacks on women during his odd seven-day crime spree were not exactly the work of a criminal mastermind.

Markoff did use black leather gloves when he attacked his first victim, Trisha Leffler, according to CBS News' "48 Hours Mystery." But the man the Las Vegas-area escort described as "good looking," and hence probably somewhat memorable, never bothered to cover or disguise his face, which she described as "dumb."

Leffler was carrying about $800 in cash which Markoff robbed her, but he also pilfered her very traceable credit cards as he waved his gun in her face. But then, Markoff took off his gloves. He proceeded to cut the hotel room phone lines, followed by three pieces of duct tape to put over Leffler's mouth. This left his fingerprints on the tape, rendering the gloves useless, at least according to Leffler. And since he never dawned a disguise, the omnipresent hotel security cameras captured the first images of Markoff at the scene of his crimes, which aided in his eventual capture.

The Craigslist Killer stole women's panties

As the Craigslist Killer assaulted, bound, and robbed his first victim, Las Vegas-area escort, Trisha Leffler, he paused for an odd bit of side business. Philip Markoff leaned over and snatched up the sex worker's panties, Leffler later recalling to CBS News' "48 Hours Mystery" reporter Peter Van Sant, "If he would've looked at my face, it would've been, like, 'What the hell are you doing?'"

Markoff had all the signs of a sex offender, according to Boston Police Commissioner Edward Davis in the "Reelz" documentary series "Murder Made Me Famous" (via People). Markoff might not have sexually assaulted his victims, but in his short crime spree, the behavior was escalating. "He took the underwear of his victims," Davis confirmed to producers, "and saved them to remember the victims."

When police eventually searched Markoff's apartment they found a trove of evidence including bullets matching his murder victim Julissa Brisman, plastic zip ties that also matched, duct tape, fragments of incriminating digital communication, and burner phones, according to Thoughtco. But more relevant to the possible sexual nature of these crimes, hidden under Markoff's mattress, police found 16 pairs of women's panties, some carefully rolled inside of socks. Neither the socks nor the entire trove of women's underwear could be traced to the existing crime spree. This led investigators to wonder if there were yet more unidentified victims — a mystery that remains unresolved.

The Craigslist Killer may have been trying to pay gambling debts

The average med student graduates with about a quarter-million dollars in debt, as of 2020, according to US News. Now imagine instead of hustling through your MD program to pay that off, you develop a nasty gambling habit on the side as well. Philip Markoff had at least $130,000 in debt, according to the Boston Herald, and was doing the most to make matters worse. 

Two days after Markoff murdered Julissa Brisman, the fledgling killer was up all night playing more games of chance at Foxwoods casino in Connecticut, where he cashed out $5,300 in winnings, according to ABC News. He also hit up a casino two nights after assailing his first known victim, Trisha Leffler. Anonymous sources told ABC News Markoff frequented Foxwoods, and had applied for multiple lines of credit. Police believe paying off his mounting gambling debts may have been part of his twisted motive. 

Markoff was long known for setting up all-night poker games, according to Thoughtco. "He earned a reputation for being a good, serious player — sometimes too serious. He wasn't a good loser." Even after his arrest and incarceration, he organized jailhouse poker games. Markoff's love of the rush of gambling alongside his impulsively violent behavior is likely not a matter of mere coincidence. According to a Polish study published in the Medical Science Moniter, "incarcerated men with a diagnosis of pathological gambling are characterized by psychopathic personality disorders, alcohol problems, and criminality."

Police found the Craigslist Killer through his wedding page

It's amazing how many infamous maniacs maintain long-term relationships despite their busy extracurricular activities. Ted Bundy had a live-in girlfriend, and eventually, later on, a daughter (albeit it isn't confirmed if the two had ever met). The Green River Killer was married three times, says Biography. Even a chilling professional hitman like "The Iceman" Richard Kuklinski had a spouse and three children.

Craigslist Killer Philip Markoff lived his double life in this same vein. He met fellow pre-med student Megan McAllister while volunteering at a hospital during his sophomore year at the State University of New York in Albany. McAllister was two years older but they became "college sweethearts" according to Thoughtco, and were engaged on May 17, 2008. McAllister also hoped to attend med school but she paused her professional ambitions to organize their wedding, which they set for August 2009.

That special day would never come, but the planning did help put Markoff behind bars. Police got a "lucky break" when the couple's now-defunct wedding webpage came up via a Facebook search. Now cops had a name for their suspect. They learned Markoff was at Boston University and got his student I.D., which matched video surveillance photos of their mysterious blonde suspect. Police then surveilled Markoff for a few days before finally swooping in to stop his reign of terror.

The Craigslist Killer didn't get rid of the murder weapon

When Craigslist Killer Philip Markoff initially appeared in court to face the charges of first-degree murder, armed robbery, and kidnapping, he brazenly shouted at the judge, "not guilty," according to ABC News.

This kind of overconfidence was a strange hallmark of his crimes. Prosecutors say Markoff used the ID of a man named Andrew Miller to purchase a 9mm firearm. But after he struck sex worker Julissa Brisman in the face with the weapon, and then shot her "point-blank" three times, the highly-educated med student — who went to some lengths to conceal he owned a gun in the first place — didn't bother to get rid of the weapon, flunking a crucial course known as getting-away-with-murder-101. 

When police eventually searched Markoff's apartment they found the weapon tucked neatly inside a "hollowed-out" copy of the medical reference text, "Gray's Anatomy." The investigation revealed Markoff had driven to New Hampshire to purchase the weapon while his fiancée Megan McAllister was away for the weekend. The Bureau of Alcohol Tobacco and Firearms was even able to match Markoff's prints to receipts for the weapon, as well as those found at the scene of Brisman's death.

The Craigslist Killer's fiancée stood by him

Get yourself a girl like Megan McAllister. When Philip Markoff was arrested in April of 2009 and charged with murder, armed robbery, and kidnapping, his fiance, initially at least, didn't waver in her support. She even wrote an email to People describing Markoff as "a beautiful man inside and out."

Despite police having "overwhelming" evidence against him (via People), McAllister asked the public not to rush to judgment against her betrothed. "I also love my fiance, and I will continue to support him throughout this legal process ... What has been portrayed and leaked to the media is not the Philip Markoff that I know," she said in the statement, via ABC News. "To me and my family, he is a loving and caring person ... he is innocent until proven guilty ... I just can only hope that the criminal justice system will not be overwhelmed and persuaded by what is being put forth in the media. My fiance's fate should not rest in the court of public opinion, but rather in a court of law."

The Craigslist Killer created a shrine to his fiancée in prison

As devoted as Megan McAllister was to her murderous beau, you can't blame her for having a change of heart. Only a month after she issued a firm statement in defense of fiance, Craigslist Killer Philip Markoff, McAllister abruptly called off the relationship, according to the Boston Herald.

The imprisoned Markoff was so distraught he was put under special surveillance and was considered a danger to himself by prison staff for the remainder of his incarceration. A year later, on August 15, 2010, Markoff was found dead in his cell on what would have been his one-year wedding anniversary.

But that's not all. Just before his death, Markoff remained so obsessed with his former fiancée he had written McAllister's name on the wall of his cell where guards could not easily see, according to ABC News. The jilted killer had also created a "ghoulish shrine" to his former partner, his body found amid photos of McAllister, fanned out on a small table in his cell, this odd little detail again per ABC News.

The Craigslist Killer went to his grave denying his crimes

It's not unusual for killers to go to their deaths unrepentant, or at least admitting nothing until they have run out of all other options. On the eve of Ted Bundy's execution, for example, with every other conceivable avenue exhausted, the serial murderer suddenly admitted to 30 slayings, more than previously thought — but also a fraction of the possible total, according to PopSugar.

Markoff's ego also wouldn't let him admit to his crimes. During a lengthy interrogation after his arrest, the med student insisted to detectives he could not even remember when he was on Craigslist, according to CBS New York, telling police blankly, "I'm listening to what you're saying –- it doesn't really apply to me. You're just telling me a story ... I don't have anything to add to it." Markoff went on to issue a flat denial, "I didn't tie up and rob anybody ... I don't really know what you're talking about." The alleged killer then wisely cut off the nearly 48-minute grilling and asked for an attorney.

After Markoff's body was found, Suffolk County, Massachusetts District Attorney Dan Conley lamented this murderer's ultimate evasion of accountability, "There was apparently a dark and sinister side to Philip Markoff that he took to his grave."