Rob Reiner and wife Michele Singer Reiner had a rocky history with President Donald Trump. Michele crossed paths with Trump before she married Rob. During her time as a photographer, she worked with Trump on the cover of his book The Art of the Deal, which was published in 1987. Two years later, Michele and Rob tied the knot. Following their nuptials, Rob and Michele didn't maintain a connection to Trump. However, their dynamic drastically changed when Trump was elected as president for the first time in 2016. Rob, who was a liberal political activist, began to speak out against Trump and his administration. "Donald Trump is the single most unqualified human being to ever assume the presidency of the United States," Reiner said in a 2017 interview with Variety. "He is mentally unfit. Not only does he not understand how government works, he has no interest in trying to find out how it works." Inside Rob, Michele Reiner's Final Days Before Son's Arrest for Their Deaths Rob continued to speak out against Trump up until his death in December 2025. Rob and Michele were killed in their home, and their son Nick was arrested on a murder charge. After news broke of their death, Trump reacted to the news by slamming Rob due to his criticism over the years. Keep scrolling for a complete breakdown on Rob and Michele's feud with Trump: 1987 Michele was hired to photograph Trump for the cover of The Art of the Deal. 1989 Rob and Michele got married after meeting while he directed When Harry Met Sally. They went on to welcome three children: sons Jake and Nick and daughter Romy. (Rob was also father to daughter Tracy whom he adopted while married to Penny Marshall from 1971 to 1981.) 2016 U.S. President Donald Trump Leon Neal/Getty Images After Trump got elected for his first presidential term, Rob is outspoken against the businessman and his administration. 2017 After Trump took office, Rob gave some insight to Michele's surprising connection to Trump. "I'll give you a story. My wife, Michele, who is a professional photographer, she took the photo that's on the cover of the book, The Art of the Deal," the comedian said during a 2017 appearance on Politico's "Off Message" podcast. "And at one point, they were up on this high-rise that he was constructing, and they were going to take the pictures overlooking Central Park. And the wind was blowing, and he said, 'I got to get this hairspray,' you know, 'I need this special hairspray.' He was always larger than life, and he was always attractive in that, you know, charismatic celebrity way." 2018 One year after sharing about Michele's involvement with Trump's book, Rob joked in an interview with The Guardian she "has a lot to atone for." 2023 When Trump decided to run again following his 2020 loss to Joe Biden, Rob shared his belief that Trump was still unfit for the job. "You have one candidate, Trump, who actually tells you he's going to govern like an authoritarian," Rob told MS NOW. "Do we want fascism or do we want to continue the 248 years of self-rule? Do we want to continue democracy or do we want to slip into fascism?" 2025 After news broke about Rob and Michele's tragic deaths, Trump shared his thoughts on the late director. "A very sad thing happened last night in Hollywood," Trump wrote via Truth Social. "Rob Reiner, a tortured and struggling, but once very talented movie director and comedy star, has passed away, together with his wife, Michele, reportedly due to the anger he caused others through his massive, unyielding, and incurable affliction with a mind crippling disease known as TRUMP DERANGEMENT SYNDROME, sometimes referred to as TDS." The president continued, "He was known to have driven people CRAZY by his raging obsession of President Donald J. Trump, with his obvious paranoia reaching new heights as the Trump Administration surpassed all goals and expectations of greatness, and with the Golden Age of America upon us, perhaps like never before. May Rob and Michele rest in peace!" Several stars and political figures condemned Trump for his comments about Rob. However, Trump doubled down on his stance when speaking to reporters at the White House. "Well, I wasn't a fan of his at all," he said. "He was a deranged person as far as Trump is concerned." Trump added that he believed Rob was "bad for our country."