They had no idea at the time – but once their faces had been doodled on his sketchbook they were just hours away from death.
Nicknamed The Doodler, the serial killer who terrorised San Francisco’s gay community in the 1970s would draw caricatures of his victims before killing them.
Approaching men in the city’s gay bars and diners, he would first charm them by handing over the sketch he’d done – then stab them to death after taking them home to have sex.
The killer is believed to have murdered at least five men between January 1974 and September 1975 – but his victims could number as many as 14.
However, although police at the time believed they had caught the killer, he was freed after three men who escaped him refused to testify, claiming their careers would be ruined if they had to admit they were gay.
But police in San Francisco have now re-opened the decades-old case, releasing a sketch of what the Doodler might look like today and offering a $100,000 rewards for details leading to his capture.
They had been encouraged by progress in another infamous cold case, the Golden State Killer, who is believed to have committed 12 murders and 50 rapes in California more than 40 years ago.
Detectives arrested 72-year-old Joseph DeAngelo in April last year after uploading the killer’s DNA to a genomics website, which identified 10 to 20 of his distant relatives.
And police believe the same website could also solve the mystery of the Zodiac Killer, perhaps the most infamous murder mystery in America.
He targeted four men and three women in the lae 1960s and early 1970s.
The serial killer earned his nickname afteer letters were sent to the local press, taunting police for being unable to find him.
At a news conference last week, police commander Greg McEachern said they had submitted DNA samples from some of the 1970s crime scenes in the Doodler case and were waiting for results from a lab.
“In the 1970s, this was gripping the gay community and San Francisco,” he said, adding that authorities were releasing the new sketch in hopes of bringing justice to victims of the “horrendous homicides.”
Inspector Dan Cunningham, head of the department’s cold case unit, said that while they had made progress on the case “this one has been frustrating”.
He said: “There just wasn’t as much attention back then to this case overall because it involved gay people.
“And some of the people involved were reluctant to come forward because of the gay aspect, and the conditions at the time.”
The series of horrific murders gripped the city’s gay community after the first murder when police received an anonymous phone call on January 27, 1974, reporting a body found near Ocean Beach in San Francisco.
“I believe there might be a dead person,” the caller said. “But I didn’t want to get too close to him because you never know what could happen.”
Responding officers discovered the body of 49-year-old Gerald Cavanaugh, who had been stabbed to death.
He had $21.12 in his pocket and a Timex on his wrist.
nvestigators found defensive wounds, indicating he fought back against his killer.
Five months later, another body – that of Jospeh ‘Jae’ Stevens – was found at San Francisco’s Spreckels Lake.
Stevens, 27, a popular female impersonator who had been named as the summer replacement at local gay club Finocchio’s, had been stabbed five times.
A few weeks after that, a German tourist called Klaus Christmann, was found dead at Ocean beach, slashed across the throat and stabbed at least 15 times.
The city’s Sentinel newspaper reported how Inspector David Toschi, who found the body, had “described the murder as one of the most vicious stabbings he has ever seen.”
Unlike the others, 31-year-old Christmann was married and had two children. According to a Homicide Division report, he was also found with a make-up tube in his pocket, which suggested “homosexual propensities”.
In May 1975, nearly a year since the murder of Christmann, the body of Frederick Capin, a 31-year-old Vietnam War veteran and nurse, was discovered on Ocean Beach.
Two months later the decomposing body of 66-year-old Harald Gullberg was found at the Lincoln Park golf course, his trousers unzipped and wearing no undergarments.
The coroner said he had been dead at least two weeks and had been hidden in an “igloo-like cove of brush near the 16th hole”.
And the murderer’s modus operandi was chilling.
The Doodler would attract his victims by drawing caricatures of them in gay clubs and restaurants in San Francisco’s Castro District, a now-famous LGBT neighbourhood.
Gay activist Cleve Jones said: ”Even now, the story gives me chills. Imagine, you’re out at a club having a drink, and someone hands you a sketch they’ve done of you. I can’t think of a more disarming ploy to gain someone’s trust.”
He would then leave with the man he’d sketched and have sex with them before becoming violent and stabbing them to death.
Four of the five victims’ bodies were found along the beach.
Although police identified the similarities in the five murders attributed to the Doodler, many believe he was responsible for many more.
When on May 2, 1975, Nick Bauman was found dead in his basement, his skull fractured, his was the 21st unsolved murder of San Francisco’s gay community since the serial killer’s spree began.
Then, in 1976, there was a breakthrough when three victims came forward claiming they had been attacked by the killer.
One was a European diplomat assigned to the States, who had reportedly met the man in a restaurant “where he was having a midnight snack”.
He then took him back to his apartment where he was suspect had stabbed him six times.
Another was an entertainer who was “nationally known”, according to police.
The third was described as “a well-known San Francisco figure”.
The victims – all white gay men – had similar injuries to those found on the bodies of the five Doodler victims.
They all gave similar descriptions of their attacker to police and one of the men even said that his attacker had been drawing caricatures on a piece of paper when they met in a late-night diner.
Victims who escaped described their attacker as a “black male, approximately 19-25 years old, lanky in appearance, with a medium complexion and smooth skin.
Police said they believed the killer had a quiet, serious personality, with an upper middle-class education and above average intelligence.
They think he was quite possibly an art student.
The statements led to police identifying a “person of interest” who was reportedly questioned on multiple occasions by detectives in 1976 and 1977 and described in press reports at the time as the suspected killer.
When he was taken into custody he had been carrying a butcher’s knife, along with a book of sketches, while the suspect’s psychiatrist reportedly told officers that he had admitted to the killing during a session.
But frustrated investigators who said they were “fairly certain” they had the right person eventually had to let him go.
An Associated Press story from July 1977 quotes officers as saying the suspect at the time could not be charged because three survivors, including a “well-known entertainer” and a diplomat were reluctant to “come out of the closet” to testify against him.
Gay rights advocate Harvey Milk said at the time about the victims’ refusal to testify: “I can understand their position. I respect the pressure society has put on them.”
It meant the case had to be sent to the cold case unit and filed away.
Speaking at a press conference last week, Inspector Cunningham said he had interviewed the diplomat again and received “promising new information”, although he had been unable to locate the name of the entertainer.
But with police believing there may be many other men who survived the Doodler, but who were not outwardly gay at the time and were fearful to report the attacks, they are hopeful that now, 40 years on, one of America’s most famous serial killings could be close to being finally solved.