Following Osborne's death last July, his wife and daughter not only faced grief, but reportedly faced debt as well.
Beginning Wednesday, they will auction off five properties and thousands of their personal assets.
On Tuesday, Osborne's daughter, Breezy Osborne-Wingfield, and his wife, Mitzi, walked through their famous white house off Cantrell Road and shared some of their memories.
"It's challenging for anybody to pack up what you know of your life and a type of legacy your family's built and just walk away," Osborne-Wingfield said.
She spent her entire childhood in the iconic Little Rock home.
"When I was little I'd put every cushion down to make the the way and I would do gymnastics and flip." Osborne-Wingfield recalled as she looked at a now empty, massive pink living room.
The Osbornes moved into the nearly 12,000 square foot property in 1976. The house holds six bedrooms, including what Jennings Osborne called his "man cave," 13 bathrooms, a pool, a hot tub, tennis court and a nine car heated and cooled garage.
All of it home to the Osborne family's memories.
"The first time I saw this room empty was last night and it was just kind of a sinking feeling...wow," said Osborne-Wingfield staring at the living room.
Calm among the chaos, Osborne-Wingfield is trying to find peace in her family's new journey without their longtime home and more importantly without her father.
"Losing his home, losing this, was his ultimate fear besides losing his life and both of those fears have come true," said Osborne-Wingfield. "I don't wish it upon my mom and I to experience it but I'm okay with him not being here, going through this."
The auction will include four other properties as well as many of the Osborne's personal assets. A large warehouse currently houses the assets up for auction which include pinball and slot machines, antique furniture, artwork and a number of fur coats.
Perhaps most intriguing is Jennings Osborne's autograph collection. The collection includes signatures from Mother Teresa, Princess Diana, Jacqueline Kennedy and George Washington, among many others. There's a baseball signed by Babe Ruth and shorts signed by Heidi Fleiss.
Osborne also had leather bound albums full of personal correspondence from a host of former presidents, governors and local law makers.
"He's definitely around...definitely," said Osborne's wife, Mitzi.
Mitzi has tried to deal with it all the best she can, but admits to crying here and there.
"It's just putting your life in a box..lots of boxes," she said. "I know it's just stuff, but it's stuff you worked for, stuff that had memories to it, you know. You can let go of anything, You can't take it with you, I sure can't this trip."
It's that resilience which will carry the Osbornes through the next several days and beyond as one Little Rock home once famous for its millions of bright lights is dim once again.
"I always hope he's never forgotten," said Osborne-Wingfield of her father. "That people always remember him and the ground that my parents laid for all of us. Just that you can give no matter what your circumstances are. You can always give back."
For more information on the auction being held from Wednesday, June 6th-Sunday, June 10 by Blackmon Aucitons, click HERE.