Five years after his retirement from the tour, Tanner ran a senior tennis event in Santa Barbara, Calif. The weekend was a success except for one thing: Tanner did not pay many of the players. He blamed it on a "sponsor screwup" and promised that the checks were forthcoming. The players had known him for years and took him at his word. The checks did arrive, but some took as long as seven months. Thinking back, former pro Dick Stockton, who played in the event and had first met Tanner in the juniors in 1961, says, "There was always an iffy side to Roscoe, things that didn't quite check out, but nothing serious enough for anyone to care."
Tanner was also, he now admits, a womanizer. He was never one to let his marriages get in the way of a good time. He met his first wife, Nancy Cook, at Stanford. They were married in 1973 and had a daughter, Lauren, in '81. But the marriage was a casualty of Tanner's infidelities--after he told her he wanted out Nancy took a pair of scissors and cut the crotch out of all of Roscoe's pants--and they divorced in '83. Not long after, Tanner met a vivacious nightclub manager in Santa Barbara named Charlotte Brady. They married within a few months, but it was only a matter of time, Tanner says, before he strayed again. "I was a smooth talker," he says. "I was good, really good, at saying whatever the other person wanted to hear."
It was the philandering that would cause the entire tapestry of his life to start unraveling. In 1993 Tanner was in New York City for a senior tennis event when he met Connie Romano, a striking woman from New Jersey. They spent a night together in his Manhattan hotel room. Tanner thought little of it--just another one-night stand on the road. (Romano says they met several times.) Then, a few months later, he got a call at the Sherwood Country Club in Thousand Oaks, Calif., where he was the director of tennis. It was Romano phoning from New Jersey to say that she was pregnant. Tanner told her he didn't think it was possible.
A few months later the summonses regarding a lawsuit for child support started arriving. Tanner says he called Romano's lawyer to discuss a settlement, but the lawyer was asking for too much money. He consented to take a DNA test, which revealed a 99.5% chance that he was the father of Romano's baby, a girl born in 1994. Nevertheless, he denied paternity on grounds that the DNA test was not conclusive enough. "He told me that he had been drugged," says Charlotte Tanner. (Roscoe denies having said this but concedes that he might have claimed he had been inebriated.) "He said that as a celebrity he was a target [of gold diggers], and I believed him." Eager to avoid bad publicity, Tanner finally agreed to a $500,000 out-of-court settlement, which at the time he did not have the means of honoring. (He claims he intended to pay Romano from $1 million he expected to make on a deal that subsequently fell through.)
When Romano received no check from Tanner and he didn't return her phone calls or respond to her lawyer's threats, she contacted authorities. In March 1997 Tanner was arrested while attending a senior tennis event in Naples, Fla., and charged with failing to appear in a New Jersey court to answer for $40,000 in missed payments to Romano. With Leonard's help, Charlotte came up with the money, and Roscoe was released. He returned to the Naples tournament the next day and, sitting in a lounge, regaled his colleagues with stories of his night in jail. When he took the court, the fans gave him a standing ovation. "Roscoe has such a way with people," says Stockton. "It was inconceivable that this great, down-to-earth guy could have done anything wrong."
Three years earlier Roscoe, Charlotte and their two daughters--Tamara, then nine years old, and Anne, four--had moved from California to Tennessee. They purchased 130 acres in the woods outside Chattanooga, which they were going to transform into the Tanner Tennis Lodge. The architectural renderings called for 140 hotel rooms, a spa, a lake stocked with fish and an upscale restaurant. Their dream was to parlay the success of the lodge into a chain of tennis resorts.
In the months after Tanner's '97 arrest, however, plans for the lodge fell behind schedule, and investors pulled out. The bank foreclosed on the property. Tanner's endorsement deals had petered out long ago, as had the lucrative pro-am appearances. In 1998 he filed for bankruptcy. Tanner turned to his pals in the tennis world for loans. "I'd say there were 25 guys Roscoe tried to borrow from," says Moore, his old doubles partner. Several players--including Borg, Tanner's opponent in that memorable Wimbledon final--stepped up, lending Tanner a total in excess of $100,000. At least Borg thought he was lending the money. When no repayment was made, his representatives pursued Tanner. Finally a deal was brokered: A portion of Tanner's earnings at senior events would be deducted to make good on the debt.
As he sank deeper into debt, Tanner was spinning an ever-widening web of lies to his wife and daughters. He had taken a teaching pro job in Florida and was seldom home. Charlotte says that on Tamara's 11th birthday, in 1996, Roscoe called to say he couldn't fly home to Tennessee due to work. Charlotte later found credit card receipts indicating that he had been in the Cayman Islands that day.
Charlotte and Roscoe were divorced in December 2000. By that time Roscoe and Margaret Barna had already had a "ceremony of commitment" in Hawaii. (Roscoe paid their bill at the Hilton Waikoloa Village with a check that bounced.) The divorce settlement called for him to pay Charlotte $7,000 a month in child support for Tamara and Anne. The checks seldom came, and when they did they were for far less than the agreed-upon amount. Charlotte filed for bankruptcy in the spring of 2001, and she and her daughters had to live apart for four months; Charlotte's credit rating was so bad that she couldn't rent an apartment. She took to selling Roscoe's tennis hardware to pay bills. The 1977 Australian Open trophy fetched $10,000, less a 15% commission. The 1981 Davis Cup trophy went for only $1,900.
In May 2001 Tanner was arrested on court during another senior event, outside Atlanta, because he was delinquent in his payments to Charlotte. He spent a night in jail for "willful criminal contempt of court" and was released after paying $8,000. Two months later another warrant was issued for him on the same charge, though he was not arrested on it.