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.