The vomiting shark that nearly took down a Sydney drug ring in 1935

On April 17th, 1935, a fisherman in Coogee Beach, Sydney, Australia, thought it was his lucky day. He’d caught a small shark on his line, which was then swallowed by a four-metre beast of a tiger shark, meaning this humble fisherman had just made the catch of his life.

What’s more, this fisherman managed to bring in this monstrosity alive. Rather than kill it, the fisherman had a better idea. Considering that tiger sharks had been responsible for the deaths of no less than three members of his local community that year, he thought his new catch would be much better placed as a special attraction for the upcoming Anzac Day celebrations that weekend.

The catch was given free run of a large pool and, as expected, people flocked to see the creature that had caused so much hardship in captivity.

For a couple of days, this creature was a spirited catch, prowling his pool menacingly and giving the people exactly what they came to see. At least, until Anzac Day itself, where he suddenly appeared a lot less active than he had previously been.

He was slow and disoriented, appearing to be quite ill in fact. It appeared he disagreed with something he ate, or, it turned out, someone. In front of a capacity crowd of onlookers, the shark started thrashing until finally he did something that probably scarred more than a few onlookers for life.

He vomited up an entire human arm.

The pool was immediately cleared, and the arm retrieved, which was when things started getting suspicious. You see, the obvious answer was that he had just regurgitated a piece of one of the citizens of Sydney that had been lost to tiger sharks, yet upon further inspection, something (and do pardon the pun) fishy was discovered. The arm hadn’t been removed by a tiger bite. Analysis of it revealed that the arm had been removed from its body by a knife, and not surgically either.

How a vomiting shark nearly took down a Sydney drug ring in 1935 -
Credit: Public Domain

What’s more, the arm was in shockingly good condition. The stomach acid of a shark is potent, yet the arm was so well-preserved that a tattoo of two boxers squaring off could still be clearly seen. This shark hadn’t spewed up its dinner, but quite possibly evidence of a murder. One that turned into a full-on investigation when Edwin Smith contacted Sydney police after reading about the arm in the paper. His brother Jim had a tattoo just like the one on the dismembered arm.

Jim Smith had also been missing for weeks.

An investigation into Smith began, and the more people looked, the deeper the rabbit hole went. Smith was a builder who’d recently been declared bankrupt, and in his desperation, turned to petty crime, mostly focused on Sydney’s illegal gambling scene. He’d last been seen drinking with his friend Patrick Brady, and after asking around for information regarding that last drink, found a cab driver who informed the police that the morning after that drink, he’d driven Brady up to the house of Reginald Lloyd Holmes.

Holmes was a respected businessman who ran a highly successful boatbuilding business. At least, that was who he was on the surface. As the investigation turned its headlights onto Holmes, the truth was exposed.

In fact, Holmes used his speedboats as part of a vast smuggling operation, bringing cocaine, cigarettes and other contraband into Sydney. One of the people employed to drive these speedboats? Jim Smith. Further investigation showed signs that Smith and Holmes had fallen out, and that the rich, respected businessman was being blackmailed by his employee.

The writing was on the wall. Holmes had put out a hit on Smith, and Brady had done the honours. However, all the evidence was circumstantial. Once Holmes denied ever knowing Smith, the investigation was back to square one. At least until May 20th. When Holmes took a boat out into Sydney Harbour and tried to take his own life. He failed and was brought in by the police. With nowhere else to turn, he agreed to talk and take the witness stand against Patrick Brady.

Patrick Brady was going to face justice for the murder of Smith, all from a tiger shark vomiting up an arm, which sounds too good to be true… because it is. Holmes was murdered hours before the trial began. With their key witness dead and all evidence pointing towards Brady circumstantial, he was found not guilty. What’s even worse is the fact that there is reason to believe Brady genuinely might not have done it after all.

Sydney was experiencing a crime wave, and after his death, it was revealed that Smith was a police informant. Meaning that several other violent criminals he’d sent to jail had motive to kill him as well. The same with Holmes as well, he was a risk to several other dealers involved with the Sydney cocaine trade, so his murder didn’t necessarily have to be connected to Patrick Brady or anyone else involved in the Smith case.

While the case of Jim Smith began with a twist of fate so spectacular it belongs in a crime novel, the rest of the story is all too real.