Many were surprised to learn his family was in financial straits this year, months after his July 27 death.
Wasn't this the same quiet yet larger-than-life businessman and philanthropist who seemed to have a dollar for every Christmas light set aglow, every heaping plate of barbecue served and every shimmering firework sent skyward in his extravagant displays of generosity?
Public cracks in the family fortune began showing weeks after he died at age 67. Debt was overwhelming his estate, and cash was needed to pay creditors. His wife, Mitzi, was forced to put their famed white-walled home in Little Rock and more on the auction block.
"People are pretty stunned, but at the same time, some people aren't shocked," said his daughter, Allison "Breezy" Osborne-Wingfield. "Our dear friends knew that this had been going on for the past couple years, and it was hard to keep rebuilding what was lost."
Jennings Osborne tried to build a new medical testing business in March 2010 and re-establish a money-making enterprise to support his charitable yet spend-thrift ways.
That he felt compelled to do this after selling Arkansas Medical Research Testing for $20.3 million in 2004 underscores his ability to plow through money.
"He's not your typical wealthy, successful guy," said Little Rock radio personality David Bazzel, a confidante.
"He had an attitude of ‘I'd rather spend my money and let people and my family enjoy it.' The negative to that is you have the situation that Mitzi and Breezy find themselves in now."
Osborne was no stranger to pushing the financial envelope. His loose handling of money prompted a trip to bankruptcy court in 1995 to gain time to pay outstanding federal taxes.
At the time, Osborne said he was embarrassed that he had to file Chapter 11 in order to work out a settlement with the Internal Revenue Service for the $361,118 owed on 1993 taxes.
It wouldn't be the last time Osborne couldn't come up with cash to pay the IRS in a timely manner. Tax liens of $1 million for tax year 1997 and $1.6 million for 2002 would come and go.
"In retrospect, he always thought he could work himself out of anything," Bazzel said. "He was the type who knew he could generate the money. I don't think he ever saw a time when he couldn't do that."
That risk-taking confidence inspired Osborne to re-enter the medical testing business and leverage his family's assets to come up with the startup capital.
"In order to do that, he took out some major loans, and he wanted to keep giving," Breezy said.
The downward financial spiral was hastened by Osborne maintaining his generous level of philanthropy while investing cash in a new business that wasn't coming out of the gates quickly.
His shaky health only complicated the launch of Osborne Research Center.
"It was a big combination of starting off slower than anticipated and he was getting sicker," Breezy said. "He knew it, but he thought he could maintain it."
A diagnosed diabetic since 1988 who had already had one heart surgery in 1996, Osborne suffered a heart attack in 2010 while mowing in the summer heat.
He checked into Baptist Medical Center for aortic valve replacement surgery on April 18, 2011, and remained there until his death 100 days later. The extended stay with intensive care treatment further taxed his family resources.
"There are some medical bills that have definitely not helped the cause," Breezy said. "There are some hefty bills. I can put it that way."
She said it was hard for her dad to concede there would be no more time extensions for him to make things right until very near the end.
His considerable will was spent, and his wife and daughter were there to reassure him it was OK.
"The only time he has given up on anything is when he admitted he was exhausted and just couldn't go on any more," Breezy said. "He couldn't tell Mom and me that he was ready to go. He had the nurses tell us."
Adding impetus to restart his medical testing business came from $6 million in lost performance-based payouts to the Osbornes after they sold Arkansas Research Medical Testing to a group of local investors led by Warren Stephens.
Jennings Osborne blamed mismanagement for the company not making the financial goals needed to generate the payouts to his family, and CEO David Jones was fired for alleged mismanagement in 2006, two years after the sale.
Osborne thought he had won a partial victory in September 2009 when a jury awarded his family $3 million in their lawsuit against the Stephens-led investors who bought the company from him.
But that verdict was appealed and finally thrown out by the Arkansas Supreme Court in April 2011.
"That was a big blow to him," David Bazzel said. "At that point, he realized he was going to have to go back and restart the business. He's a live-in-the moment kind of guy and liked to do things big and fast."
Breezy Osborne has taken her family's financial setbacks in stride, saying, "It is what it is."
Her focus is doing what she can to help her mom while running her Little Rock yoga business, Barefoot Studio, and preparing for the August birth of her first child: a girl, Riley Jennings Wingfield. She and her mom appreciate the outpouring of goodwill toward her family.
"People have been incredibly supportive with prayers and help," said the mother-to-be. "People want to be there for us and do things."
That's a sentiment her father would appreciate.
June: Jennings and Mitzi Osborne sell their Arkansas Research Medical Testing for $20.3 million to a local investment group led by Little Rock financier Warren Stephens. The deal includes annual performance-based payouts of $3 million for three years.
Oct. 10: The Osbornes sue Arkansas Research Medical Testing LLC and its owners in Pulaski Country Circuit Court seeking $6 million in damages. The Osbornes claim the owners are liable for the mismanagement of the company, which cost them performance payouts in 2005 and 2006.
Sept. 18: The jury returns a $3 million verdict in favor of the Osbornes after a four-day trial.
Feb. 10: Axient Research, the renamed Arkansas Research Medical Testing, announces the company will be closing.
March: The Osbornes re-enter the medical testing business by opening Osborne Research Center in downtown Little Rock.
April 14: The Arkansas Supreme Court overturns the $3 million jury verdict.
April 18: Jennings Osborne undergoes heart surgery to replace his aortic valve after suffering heatstroke and a heart attack nine months earlier.
July 27: Osborne, diagnosed with diabetes in 1988, dies at age 67 after spending 100 days at Baptist Medical Center following the surgery.
Sept. 11: Metropolitan National Bank of Little Rock files a foreclosure suit against Osborne Aviation and Mitzi Osborne to recover $1.2 million. The debt is secured by Osborne Aviation's 22-passenger corporate jet and a second mortgage claim on the Osborne's lake house in Hot Springs.
Feb. 6: Metropolitan National Bank files a foreclosure suit against Mitzi Osborne and her daughter, Breezy, to recover $166,659. The debt is secured by second mortgage claims on Breezy's west Little Rock home and a house adjoining the Osborne's famed Cantrell Road residence.
May 2: Blackmon Auctions of Little Rock announces it will oversee the sale of five residential properties and other Osborne family assets June 6-10.