In December 2016, Jim was introduced to Woodhead's supplier - a man named Tadgh Kiely. In exchange for being able to buy direct from Kiely, court facts say Jim promised Woodhead $1000 every time he dealt with Kiely. Over lunch at Bondi's Cock and Bull hotel, Kiely told Jim that he ran a nationwide drug business that frequently took him to Adelaide, Darwin and Canberra. He promised he would import ecstasy from Europe via the dark web for Jim, at a cost of $1000 per transaction. True to Kiely's word, the syndicate sold Jim larger and larger volumes of drugs in 2017. In March that year, Jim paid a $50,000 for a kilogram of MDMA that he bought from Woodhead, Domino's delivery boy Nguyen Huynh, UTS business student Angel Bowyer, 19, who was Huynh's girlfriend, and an unknown associate. As the year progressed, members of the syndicate continued to meet Jim to sell increasingly large amounts of drugs at locations across Sydney including a suburban Chatswood street, McDonald's at Mascot, his car outside Central Station and the Hoochie Mama cafe in Newtown.

Come April, Huynh - Wickr user name d0pemaann88 - was telling Jim he could supply MDMA by the kilogram; $40,000 later, he had it. But it all fell over in May 2017, when Jim arranged to buy $120,000 worth of MDMA and $73,000 worth of cocaine. Another member of the syndicate, whose parents' home was used for multiple deals, told Huynh that the MDMA was hidden outside. "Come to the right side of the gate … it'll be 100% safe," he said in a text message tendered in court. It wasn't. After Huynh and Bowyer took $193,0000 from Jim and handed over the drugs, officers from Strike Force Teribah swarmed and arrested them, the man whose parents home was used for the drop and another man who had been acting as a lookout.

The next day, Kiely was arrested when he flew back into Sydney. He told investigators he let his "mind get carried away" and he didn't personally have the means to supply large amounts of drugs. "[I'm] not the sort of person with kilos of MDMA to supply personally," he told detectives. "There is a buyer and a seller, and I'm just the little person that slots in the middle." Woodhead was arrested the same day, as police raided his Lane Cove sharehouse. He was charged with six counts of supplying a prohibited drug and one count of participating in a criminal group.