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Another of Scott's friends suggests that Scott had a rough relationship with his mother and projected his need for approval onto Ashley.
"Clearly, he was proving himself," the friend says of Ashley. "Then she left, and he felt like he'd failed. He had no one to prove himself to anymore. His mother was dead. His new wife left, even after he gave her everything. And his business was in the tank, too."
Between 2004 and 2006, Scott pursued Ashley and became the flamboyant millionaire whom many remember.
"He kind of turned into a wanna-be rock star there for a while," says Mike Denning, former president of Mortgages Ltd.
Coles' vacations included skiing in Chile (where one unsubstantiated rumor suggests he was preparing an off-shore hideaway), gambling in Las Vegas, and flying in his private jet to his numerous other estates.
Coles' favorite restaurant was T. Cook's at The Royal Palms. With his family, he often ate at more plebeian Biltmore-area restaurants: Postino and California Pizza Kitchen.
Scott's perfectionism surfaced in every facet of his life, according to friends. He could be golfing on his course and suddenly call his groundskeeper to have his flowers freshened.
During a dinner party at Rockridge in 2007, Coles reportedly lost his temper with a housekeeper who spilled a drink on a tablecloth, according to another acquaintance of Coles.
Coles stormed into the kitchen, grabbed a club soda, and started scrubbing the stain himself, the acquaintance says.
He was also a regular at black-tie fundraisers and upper-class galas. His attendance at those events has been touted in most stories about him.
Now, the investors who dumped their retirement and home equity into Mortgages Ltd. don't feel as cheery about Scott's big-ticket purchases and generous donations.
"What's been bothersome is all this talk in the news about Scott giving money to everyone, being so generous to the boys club. Well, he was also living in an $11 million home," says Sidney Madison, one of numerous investors who could lose their entire retirement and life savings in Mortgages Ltd.'s bankruptcy.
Another investor, Barbara Porter, 62, nearly withdrew her investment as Scott Coles' behavior grew more flamboyant. She had invested with Chuck Coles back in the 1970s — when Scott was still running around the playground at Madison Meadows.
"I thought several times, maybe I should take it out," says Porter, adding that she's broke because of the company's bankruptcy.
Porter, a widow, has put her Gilbert home up for sale and is now hunting for a job to support herself and her disabled adult daughter. She invested every penny of her savings and retirement (hundreds of thousands of dollars) into Mortgages Ltd.
Three weeks before Scott's death, Porter heard rumor of troubles at the company and spoke with Scott personally. "Scott said, 'None of this is our fault. A lot of companies aren't paying what they owe us.'"
But Porter disagreed, telling him, "Yes, Scott, it was your fault, because you loaned them the money."
She said Coles always told her that he "only loaned 50 cents on the appraised dollar."
Porter and other investors have since learned that Coles' recent loans were not made at 50 cents on the dollar. In fact, some properties are worth far less than what the debtors owe.
"Scott talked so fast and over the top of my head. I'm sure he knew exactly what he was saying, but I never was impressed," Porter says.
As Scott pursued Ashley and lived the high life, he was also busy transforming Mortgages Ltd. from a modest and profitable operation to a cash cow that churned out surreal amounts of money.
Scott devised numerous ways to make more money on both investors and borrowers, both coming and going. He also leveraged his growing reputation and lavish estates to court investors and borrowers.
It took Coles about eight years to convert his dad's conservative, 35-year-old business into a high-risk machine.
Friends joked that he would end up owning all the real estate in Arizona.
As Coles took on increasingly risky projects, his advisers cautioned him to be more careful. But Coles didn't listen, sources say, particularly not recently.
"Scott became extremely autocratic," says a former Mortgages Ltd. employee. "All the loans, everything, were made strictly by him. Even though loan officers would recommend against approval, he would go ahead and approve them. There wasn't a single officer I know of in the company that agreed with the leveraging and the concentration in the portfolio that Scott was pursuing."
In November 2005, Coles' right-hand man of 13 years, Jim Cordello, left the company. He was the first of many executives who came and left with unusually high turnover during the past three years.
Cordello did not return calls for this story, but in a 2006 court deposition, he said he left Mortgages Ltd. because Coles verbally promised him a year-end bonus — but broke his word.
That's not the only promise Coles broke, business associates say. Investors and borrowers alike say that Coles' promises grew bigger and more impossible as his company unraveled.
"He was a very high-profile guy, well-known and wealthy," says Rick Burton, a multimillionaire developer and principal of Rightpath Development.