Rob Reiner's wife Michele photographed Trump's iconic cover photo for 'Art of the Deal'

The image showed Trump in his 40s, projecting the confidence and ambition that cemented his persona in public life
Long before President Donald Trump forayed into politics, an iconic image in his rise to fame passed through the lens of filmmaker Rob Reiner's wife Michele Singer Reiner (Amazon, Getty Images)
Long before President Donald Trump forayed into politics, an iconic image in his rise to fame passed through the lens of filmmaker Rob Reiner's wife Michele Singer Reiner (Amazon, Getty Images)

WASHINGTON, DC: Long before Donald Trump forayed into politics, an iconic image in his rise to fame passed through the lens of Michele Singer Reiner.

Singer Reiner was a professional photographer before marrying director Rob Reiner. She took the photograph that appeared on the cover of Trump’s 1987 ghostwritten bestseller, 'The Art of the Deal.' The image showed Trump in his 40s, projecting the confidence and ambition that cemented his persona in public life.

(Amazon)
Donald Trump's iconic image on his bestseller was gaken by Michele Singer Reiner (Amazon)

That legacy resurfaced this week amid a tragedy that has shaken Hollywood and Washington alike.

Deaths in Brentwood under investigation

Michele Singer Reiner and her husband, filmmaker Rob Reiner, were found dead in their Brentwood home on Sunday, December 14. Police have taken the couple’s son, Nick Reiner, into custody. 

Rob Reiner and Michele Singer Reiner arrive on the red carpet at the State Department for the Kennedy Center Honors gala dinner, Dec. 2, 2023, in Washington. (AP Photo/Kevin Wolf, File)
Rob Reiner and Michele Singer Reiner arrive on the red carpet at the State Department for the Kennedy Center Honors gala dinner, Dec. 2, 2023, in Washington (AP Photo/Kevin Wolf, File)

Authorities are investigating the deaths as an “apparent homicide.” On Monday, police announced that Nick Reiner had been booked on murder charges and was being held on $4 million bail.

LOS ANGELES, CA - AUGUST 09: Actor/Producer/Director Rob Reiner (center) and wife Michele Singer (L) and son Nick Reiner (R) attend Teen Vogue's Back-to-School Saturday kick-off event at The Grove on August 9, 2013 in Los Angeles, California. (Photo by Michael Buckner/Getty Images for Teen Vogue)
Actor/Producer/Director Rob Reiner (center) and wife Michele Singer (L) and son Nick Reiner (R) attend Teen Vogue's Back-to-School Saturday kick-off event at The Grove on August 9, 2013 in Los Angeles, California (Michael Buckner/Getty Images for Teen Vogue)

Trump blames ‘TDS’ in Truth Social post

News of the tragedy sparked reactions across social media, but the most controversial came from Trump himself. In a Truth Social post, the president appeared to blame Reiner’s political views for his death.

“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,” Trump wrote.

WASHINGTON, DC - DECEMBER 15: U.S. President Donald Trump speaks during a ceremony for the presentation of the Mexican Border Defense Medal in the Oval Office of the White House on December 15, 2025 in Washington, DC. During the ceremony, Trump recognized the first 13 service members to receive the recently established Mexican Border Defense Medal (MBDM), which recognizes service members supporting Customs and Border Protection on the U.S.-Mexico border. (Photo by Anna Moneymaker/Getty Images)
U.S. President Donald Trump speaks during a ceremony for the presentation of the Mexican Border Defense Medal in the Oval Office of the White House on December 15, 2025 in Washington, DC (Anna Moneymaker/Getty Images)

The term is commonly used by Trump supporters to describe people they believe have an obsessive hatred or fixation on Trump.

The president suggested that Reiner’s “obsession” with him may have played a role in the killing.

“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,” Trump said. “May Rob and Michele rest in peace!”



A long-running feud with Trump

Rob Reiner had been one of Trump’s most vocal critics for years.

A strong supporter of progressive causes and Democratic candidates, Reiner publicly questioned Trump’s fitness for office. In a 2017 interview, he described Trump as “mentally unfit” to be president.

The following year, Reiner accused Trump of “treason.” In an October interview with MSNBC (now MS NOW), Reiner said the political climate under the Trump administration was “beyond McCarthy era-esque.”

Rob Reiner attends the screening of
Rob Reiner attends the screening of "Misery" during the 2025 TCM Classic Film Festival at TCL Chinese Theatre on April 25, 2025 in Hollywood, California. (Photo by Jesse Grant/Getty Images for TCM)

The ‘Art of the Deal’ connection

As reactions poured in, CNN senior reporter Edward-Isaac Dovere reminded readers of Michele Singer Reiner’s little known role in Trump’s early branding.

“Michele Singer Reiner shot the photo on the cover of The Art of the Deal,” Dovere wrote.

He also recalled a story Reiner himself once shared about the photoshoot. “Rob Reiner in 2017 to me on Trump: [The photoshoot] was overlooking Central Park, and the wind was blowing, and [Trump] said, ‘I gotta get this hairspray. I need this special hairspray.’…He was always larger than life.”



As mentioned, the cover image played an important role in amplifying Trump’s public image. Ghostwriter Tony Schwartz later said the photo reinforced the book’s portrayal of Trump as the “emblem of the successful tycoon.”

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