...By then, Ali had found a new friend. In the spring of 2017, comedian Kathy Griffin’s life was quickly unraveling following a photo shoot in which she posed holding a prop resembling Donald Trump’s decapitated head. Death threats poured in by the thousands. Griffin was promptly fired from her gig at CNN, venues canceled her upcoming comedy tour, and lucrative endorsement deals disappeared overnight. The Secret Service launched an investigation. Griffin was as radioactive as a celebrity could get. Desperate, she turned to an unlikely savior—one of her favorite Twitter personalities who’d often been complimentary about her on the platform.
She DM’ed Ali, and as fate would have it, they discovered a weird connection: they’d both attended the same high school in Chicago, and Ali recalled attending a party at her house in L.A. years later. Initially, they discussed simply doing an interview to clear up the Trump matter. But as their relationship grew closer, Ali morphed into Griffin’s unofficial advisor and shadow publicist. He introduced Griffin to sympathetic journalists, schooled her in the intricacies of social media, and strategized about which publications and late-night talk shows would best serve her career rehabilitation. Eventually, Ali took an even more active role in her comeback, writing a glowing profile of Griffin for New York. When Ali said he was coming to L.A. in the spring of 2018, Griffin invited him to stay at her 13,000-square-foot Bel-Air mansion. According to a source close to Griffin, he ended up living there for nine months. (Ali insists he stayed less than six.)
Playing a similar role for Griffin that he’d played for Newsom and Buell, Ali became the comic’s confidante-slash-executive assistant, though he was never on Griffin’s payroll. He took an active role in managing Griffin’s social media accounts, helped her set up a merchandise company, and came to her defense in a property dispute by posting an embarrassing audio clip of a wealthy neighbor screaming expletives. He made a brief cameo in a Keeping Up With the Kardashians Christmas special, which he attended as Griffin’s guest. He did Griffin’s grocery shopping and cooking, jobs that usually fell to Griffin’s paid staff. In exchange, she let him live in her home rent-free and lent him one of her cars. But as the months wore on, Ali became increasingly reclusive, holing up in his bedroom and rarely leaving the house. Staff members assumed he was busy writing, but people around Griffin grew concerned when he started receiving official government mail at her home address.
One evening in the fall of 2018, Griffin invited journalist Joan Walsh, the national affairs correspondent for The Nation and a former political analyst for CNN and MSNBC, to join her for dinner. After Ali made an appearance, Walsh began probing Griffin about the nature of her relationship with him. Walsh says she got the sense that Griffin wanted Ali to leave but was too intimidated to force the issue. “I completely believed that she was uncomfortable and maybe even afraid, and I sympathized with her,” says Walsh. After listening to Griffin’s story and seeing her evident anxiety, Walsh told her host, “Kathy, you got yourself a grifter. You have to get him out of here.”
It would take several more months, but Griffin finally asked Ali to leave in early 2019, enlisting two part-time male assistants to help oversee the packing of his belongings. Then they ordered him an Uber and sent him on his way. (Ali says he only stayed with Griffin at her urging, and left of his own volition. He says the comedian even threw him a going-away party when he moved out.) Griffin declined to speak about Ali on the record. However, a representative for the comedian offered a statement on her behalf: “Sometimes you make a new friend and that friend turns out to be quite a different person than you thought they were.”