As Anna Nicole Smith entered the spotlight in the 1990s, there was one person who was always at her side: her son Daniel Wayne Smith. Daniel was born in 1986 when she was married to her first husband Billy Wayne Smith; they were teenagers when they tied the knot and later divorced in 1993.

Anna Nicole and Daniel had a close relationship. She once told PEOPLE, “The best present he ever gave me was this plaque he made that says, ‘I Love You, Mom. Your son forever.'”

Daniel tragically died on Sept. 10, 2006, just three days after Anna Nicole gave birth to daughter Dannielynn on Sept. 7. He was 20 years old.

Daniel had just flown from Los Angeles to the Bahamas to see his mom and meet his new sister, but hadn’t been feeling well,

David Giancola, director of Anna Nicole’s movie Illegal Aliens, told PEOPLE shortly after Daniel’s death. “They weren’t sure if they should put him on a plane, but Anna wanted him to be there, and Daniel wanted to go,” he said.

He arrived in Nassau late on Sept. 9 where he met his little sister and embraced his mother at the hospital. Howard K. Stern, Anna Nicole’s lawyer and partner, was also on hand. Everyone eventually fell asleep, though a hospital worker remembered seeing Daniel still tending to his mother in the early morning.

But when Anna Nicole woke up later that morning, she realized Daniel wasn’t breathing. Doctors tried to resuscitate Daniel, and at 10:05 a.m., he was pronounced dead. Michael Scott, Anna Nicole’s Nassau lawyer, told PEOPLE she “was so distraught, she refused to leave Daniel’s side, and it was necessary to sedate her in order to check her out of the hospital.”

A family friend told PEOPLE of Daniel’s bond with his mother, “He did whatever his mom said, whether it be doing the dishes or laundry. Come Friday or Saturday nights, he’d spend them watching movies with his mom and Howard Stern. They were glued together.” The pair “adored each other.” Giancola told PEOPLE Daniel was “very mature” and aspired to be a producer.

An autopsy ultimately found that Daniel had died from a combination of drugs, including methadone and antidepressants. A Bahamas jury ruled in March 2008 that his death was an accidental overdose and did not recommend criminal charges, per CBS.

In a November 2006 interview with Entertainment Tonight, Smith said she didn’t remember anything from the day Daniel died, except when Stern told her he was dead.

“I thought they were playing that game they play on TV… Punk’d,” she said. Later in the interview, through tears, she said, “I don’t understand why God took him and didn’t take me.”

Anna Nicole died five months after Daniel’s death, in February 2007. Her death was also ultimately ruled an accidental drug overdose.

“You’ve got to think: My daughter was born on Sept. 7 and on Sept. 10, Daniel died,” Larry Birkhead, Dannielynn’s father, said in February 2017. “So you go from that extreme high and low, and how do you process that in your mind? Although her death certificate will list a different cause — an accidental overdose — in my mind, I think she truly died of a broken heart.”