The Irish woman at the top of Hugh Hefner's Playboy empire


“That was a big age difference when you are as spunky as I was,” O’Connor joked.

After her first marriage came to an end O’Connor married a further three times, each relationship ending.

However, a little more than 20 years ago, she finally met her soul mate, Captain Bob. I remember him from the show. They are a great couple.

O’Connor moved out to California in 1953 after she separated from her second husband.

“I always wanted to come here. My father’s sister was a screenwriter and involved in the movies and that fascinated me,” she said.

But it wasn’t the movies that caught O’Connor’s attention. It was the speed of a car.

It was through her second husband that she fell in love with the buzz surrounding racecar driving. Not only did O’Connor promote road races across the country, she competed several times in them.

As O’Connor’s life was steadily becoming hectic she was thrown into the life of playboy bunnies, Hugh Hefner and the excitement and glamour associated with the world of being sexy and rich. 

While serving on the board of advisors of a hospitality magazine she was approached by another board member of take up the position of manager of the Playboy Mansion in Chicago.

After some careful thought, O’Connor agreed to go working for one of the most powerful men in the U.S., and hasn’t looked back since.

“I moved to Chicago in 1969 and at the time there were 24 bunnies living in the house,” she said.  “It was a whole new experience and a whole lot of fun.”

In 1971 Hef purchased the mansion in LA and for a few years O’Connor would travel between the two until he finally moved himself and his bunnies to sunny California.

“I had great fun furnishing this house,” O’Connor told us as we looked around.

“It was so much fun going into a store when money wasn’t an issue.”

O’Connor has been with Hef for more than 40 years and has no intention of retiring.

She works 9 a.m. to 5 p.m., sometimes seven days a week.

It was Hef’s birthday on the Friday after we were at the mansion.  O’Connor and her staff were busy putting in place celebrations for a big bash, and then it was off to Las Vegas with the whole lot of them (including O’Connor) to continue the celebrations.

As for the Girls Next Door show, O’Connor said that she wasn’t very fond of the idea of being featured on camera every day when she came to work, but she said after a while she became used to it.

O’Connor’s day consists of sitting in her office and spending hours meeting with Hef to discuss business issues.

“I see more of Hef than I do of anyone else,” she laughs.

O’Connor maintains a strong relationship with several of the previous playboy bunnies, some of whom were Hef’s girlfriends.

This is particularly true for her relationship with Kendra Baskett. O’Connor has appeared on the show Kendra several times.

“The girls know I’m here if they need me,” she told us. showing her motherly side yet again.

O’Connor is no stranger to Ireland. In 1986 she visited the south with Captain Bob and thoroughly enjoyed it, but had one regret.

“We didn’t get to go up to the north of Ireland where my family are from,” she said disappointed.

However, O’Connor plans to go back for a little over a week next year with her friend Jason McGimpsey and explore the land of her grandmother.

“That’s really important to me,” she said. “I’m really looking forward to that trip.”

As our interview came to a close I asked Rob if Hef was anywhere in the mansion. He was! Upstairs in his sleeping quarters.

He normally doesn’t rise till after 11 a.m., at which time he joins O’Connor in her office to run through the day’s business.

We left the Mansion that day feeling excited but also proud that an Irish American woman is part of the reason Hef is so successful, grounded and so full of devilment.