- Attacked by feminists on the left, the government on the right and competitors in the middle.

Hefner retreated every other week to his West Coast mansion.

- I think Hefner was always destined for LA.

Hefner was kind of seduced by stardom in the same way that people were seduced by his stardom.

I think he believed that Chicago was small town America, and in a way it is.

I mean, it's a big city with a small town heart.

Playboy, I think, had a romance with Chicago, and I don't honestly know if Chicago had a reciprocal romance with Playboy.

- Hefner's ties to Chicago unraveled in March 1974.

Agents from the Drug Enforcement Agency arrested Bobby Arnstein in front of the mansion with a cocaine vial in her purse.

Hefner's beloved secretary was already emotionally fragile and now stood accused of helping a boyfriend transport a half pound of cocaine from Florida to Chicago.

- They were all convinced that Hugh Hefner and the Playboy Mansion was somehow a center of drug use and drug distribution.

- The US attorney for the Northern District of Illinois was the same prosecutor who had tried Lenny Bruce a decade earlier.

James Thompson, - Big Jim Thompson, did not like Mr. Hefner and went after him.

- Hef did not do cocaine while I was with him.

They did not want to do drugs other than the dexedrine to stay awake and marijuana.

- Prosecutors leaned on the testimony of a convicted drug dealer who had changed his story about Arnstein's involvement in Miami.

Arnstein was convicted of conspiracy to distribute cocaine and sentenced to 15 years in prison.

- I don't think you ought - To give any statement at all.

No, I think it's absurd.

Do you think you ought to give any statement.

My lawyer suggests that I not give any statements.

It's not my personal feeling.

Sorry.

- He blamed the government.

He said they're relentless, they're after me, and they're using her as a pie.

- Though Einstein's lawyers explained she would likely get a reduced sentence, perhaps even probation.

She sank deeper into depression and drug use - Not too long after that, went to a a local hotel or on Monroe Street and committed suicide.

- Einstein's suicide gutted Hefner.

He flew back to Chicago for a hastily called press conference.

- She was one of the best, brightest, most worthwhile women I ever known.

She will be missed.

- Hefner served as a pallbearer at Arnnstein's funeral, the first he had ever attended.

- It just devastated my father that she'd been driven to this by, and I will say it by Jim Thompson, who was busy putting scalps on his belt for his own political aspirations.

- The prosecutor denied targeting Hefner.

I have no quarrel with him, his philosophy, or his magazine.

The Justice Department dropped its case against Hefner.

11 months later, Thompson was elected governor the next year winning the first of four terms, - A classic corrupt Chicago political moment.

It crossed a line, it took a life, and he left.

- Hefner's nine year romance with Benton also faded out - For Hef.

It was an eternity.

He just didn't behave himself.

I was smart enough to leave Hef.

I don't know why I didn't leave him sooner, but we always had a good time - Though the white hot center of the Playboy universe gravitated West, the beacon over its Michigan Avenue headquarters never dimmed.

- We were producing a magazine out of that building with the same gusto the day before he moved as the day after he moved.

There was Hef, but the, the force of the magazine was in Chicago - And it was in Chicago where another Hefner, straight out of central casting began her rise.

- Have you been comfortable with the way the magazine has treated women over the years in its presentation of women?

- Pretty much so.

I think you have to start from the underlying assumption of the magazine, which is it's for men and not for women.

And therefore, - When I saw the way she could speak to people who I didn't ever think he was comfortable speaking to, you know, the kind of people who make the machinery of this empire work, I knew she could do that.

- As Christi ascended to President and CEO of Playboy Enterprises, her relationship with her father deepened, - It was really gratifying for me to see how much he respected me, how proud he was of me.

He got a huge kick outta the fact that I was working in the company.

- Well, I am much blessed and you know, at the top of the list of many things I would've to rape my daughter, - Hefner hunkered down in his west coast mansion, weathering good years and bad marriages, divorces and scandals, including disturbing allegations of abuse and sexual misconduct.

- Come in.

- Hefner remained sentimental about Chicago, though weary of the politics that hastened his exit.

- He came back more than once.

- I'll just tell you, these were the best years of my life.

- He went back to Steinmetz to speak to the students.

- I think that this particular period of adolescence and growing into young adulthood is what it's all about, because that's really the beginnings of everything.

- You know, for all the conflict that he had in Chicago, you know, with the Catholic church with the Daley Machine.

I think he remained incredibly fond of Chicago.

- I asked Hefner what this trip home had meant to him.

- Magic, you can go home again.

- Hefner died from cardiac arrest in 2017.

He was 91 years old, and his complicated legacy continues to stir debate.

His presence has faded in the city where he became one of the 20th century's most influential magazine editors.

The mansion was carved up into luxury apartments and the site of the first Playboy Club is now a parking garage.

The magazine ceased publishing a US print edition in 2020, but the bunny ears are still recognized around the world.

And no other Chicagoan made a bigger global impact, for better or worse than Hef.

- As Hef once famously said, it's like a Rorschach test.

You know, there are people who read it and find it really threatening and offensive, and there are people who read it and love it.

It's the same magazine.

- Hefner was buried in Los Angeles next to the screen siren, who made all his dreams come true.

- It really was a Chicago story for me.

I, you know, I love this town.

My dreams came from here and I started the magazine, you know, with a Chicago dream.