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Book excerpt: How con man got 20 years for Brach death — without being convicted of killing her

Second of two parts

Adapted with permission from “Who Killed the Candy Lady?” by James Ylisela Jr., Agate Publishing, 2014. Available at

Richard Bailey’s sentencing hearing took place in late May and early June of 1995.

The task before U.S. District Judge Milton Shadur was to determine an appropriate prison sentence for the fraudulent acts the con man had admitted, then to add more time if the government could show by “a preponderance of the evidence” he also had conspired to murder candy heiress Helen Brach.

Bailey had pleaded guilty to 16 counts of racketeering and fraud. One factor influencing his sentence was whether the con man showed remorse.

Prosecutors portrayed Bailey as a malicious, unfeeling predator of vulnerable women.

Defense attorney Patrick Tuite put Bailey on the stand to tell his side of the story.

“We thought he would be a little more remorseful,” Tuite told me. “But he wasn’t. He kept trying to explain everything.”

While Bailey admitted to cheating women, he insisted he never defrauded Helen Brach, not even in 1975, when he and his brother sold her three race horses for $98,000, though they had paid only $17,500 for them.

Bailey’s testimony was contradicted by Arthur Katz, who with his father had designed elaborate memorial stones for Brach, her family and even her pets.

Katz testified his father had been a close friend of the candy heiress Brach had visited his father at his office shortly before her disappearance. She was complaining about being cheated in a horse deal by a younger man she was dating who had made arrangements for her trip to the Mayo Clinic. His father offered to take Brach to the state’s attorney upon her return, and she agreed, Katz said.

The elder Katz died in February 1978, a year after Brach’s disappearance, without ever having contacted authorities. A year later, his son wrote to the administrator of Brach’s estate detailing his father’s concerns.

At the sentencing hearing, Bailey’s lawyers tried to challenge Katz, arguing he wrote the letter only after learning Brach’s estate had posted a sizable reward for information about the disappearance.

When Bailey took the stand, Tuite asked, “Did you have anything to do with the death or disappearance of Helen Brach?”

“Definitely not,” was the reply.

The government needed to show only that it was more likely than not that Bailey had conspired to kill Brach to boost his sentence for his fraud and racketeering conviction.

Prosecutors relied heavily on the testimony of a few witnesses whose lack of credibility was astonishing.

There was Cathy Jayne Olsen, the 41-year-old daughter of horseman Frank Jayne Jr. and great-niece of the late horseman Silas Jayne. Olsen testified she’d given Brach riding lessons and once sold her a grey horse.

One day, Olsen testified, she was hiding in a supply closet in her father’s office when she heard Bailey and her father talking about Brach. The heiress knew too much, Olsen testified the men were saying, and “we had to shut her up.” Some time later, she testified, she was back in the closet in time to hear the men say Brach had indeed been silenced.

It was a compelling tale. But Olsen’s story contradicted her grand jury testimony in 1990, when she had neglected to say Bailey was present in the barn that day.

Under cross-examination, she admitted being an alcoholic and cocaine addict who had accepted thousands of dollars from the government and immunity from prosecution in exchange for her testimony. “I told them a lot of stories to get into the hospital,” she conceded.

Donna Hunter, Frank Jayne Jr.’s common-law wife of 16 years, told me that Olsen’s story was completely false. In a 1999 interview, Hunter said Olsen had confused Brach with another woman Bailey had been dating.

As for the conspiratorial conversation, Hunter said it never happened. “Cathy, nor one-third of her, could have fit in that supply closet,” she said. Hunter said she tried to explain this to prosecutors, but they never put her on the stand.

Bailey himself points out a flaw in Olsen’s story.

“Helen owned race horses, and liked to go to the track to watch them run,” he told me from his Florida prison. “But she never rode a horse in her life.”

The government’s star witness was Joseph Plemmons. If there was a better con man than Richard Bailey, Plemmons took the prize. While Bailey showed off horses and sold them at inflated prices, Plemmons did him one better: He sold horses by showing photographs of animals he never owned nor had any intention of delivering.

At 47, Plemmons was a good-looking, affable witness. He testified other horsemen used to tease Bailey, asking how he could have sex with the older women he was conning. He said Bailey replied, “I close my eyes and think about the money.”

His story of a fateful lunch with Bailey enthralled the courtroom: On a warm day in February 1977, Plemmons said he joined fellow horseman Kenneth Hansen for lunch with Bailey at a restaurant.

“Richard said that he was in trouble,” Plemmons testified. “And he looked at me and said the Candy Lady wasn’t so sweet anymore, and he was in trouble. That he thought that she was going to go to the authorities. He could not stand the heat. And he wanted to know if we could make her disappear for $5,000.”

Bailey didn’t just want Brach dead, Plemmons said: “He wanted no one ever to find her.”

He testified that Hansen said he “wouldn’t kill an old lady” and excused himself to go to the restroom. Plemmons said he also turned Bailey down. Two weeks later, Brach disappeared.

Plemmons’ testimony was the government’s most direct evidence that Bailey solicited Brach’s murder.

When Bailey himself took the stand, he made a fatal error. Hotel records showed Bailey had checked in to the Colony Hotel in Palm Beach on Feb. 16, with a girlfriend from Chicago, Christina Kubot. But after Plemmons’ testimony, Bailey claimed he had actually left for Florida on Feb. 10.

But Assistant U.S. Attorney Steve Miller produced phone records from Bailey’s Lake Shore Drive condominium, showing calls to Kubot and to Frank Jayne Jr.’s Northwestern Stables between Feb. 10 and 13. Bailey had lied, and the phone calls proved that he was in Chicago and backed up Plemmons’ story, Miller charged.

“Richard kept saying he was in Florida,” Tuite told me. “They had phone records in Chicago. He was making up things on the stand.”

In a final dramatic flourish, Miller announced he had a surprise witness, a teacher named Pamela Milner, who claimed Bailey had confessed when they were on a date in 1989 to having killed Brach. Milner testified Bailey took her to a seedy bar, became agitated and started raving about how he had “taken care of the Candy Lady.”

She said she thought her life might be in danger. After Bailey took her home, Milner said, she pulled a pay stub out of her purse and jotted down what Bailey had said, dated it March 17, 1989, and later put it in a safe-deposit box.

Tuite, though, shredded Milner’s story. He produced a copy of the paystub, which was dated October 1989, not March, and raised other inconsistencies in Milner’s story. She fell apart on the stand.

Tuite still can’t believe the government produced a witness like Milner.

“You know, she came to us first, asking to be a character witness for Richard,” he told me.

The judge struck her testimony from the record even before Tuite could complete his cross-examination.

In his closing argument, Assistant U.S. Attorney Ron Safer argued there was no reasonable explanation for Helen Brach’s disappearance “other than she was silenced by Richard Bailey and his co-conspirators.”

Safer argued the testimonies of Plemmons and Olsen provided proof Bailey was involved.

From the start, Bailey’s lawyers had maneuvered to cast doubt on the government’s case by raising suspicions about another man — John “Jack” Matlick, who had worked or Brach’s husband and then for her and was the last person to claim to have seen her

Ron Menaker, Tuite’s co-counsel, said in his opening statement that “there is a person who could help us in our understanding of Brach’s disappearance. That person is Jack Matlick.”

But Judge Shadur quickly shut down that line of argument. “No federal jurisdiction on Matlick, right?” he asked the lawyers, who had to concede there was no evidence connecting him to the conspiracy and racketeering charges facing Bailey.

But in his closing argument, Tuite tried one more time. The real killer, he said, was Matlick, who had evaded the government’s scrutiny because he couldn’t be indicted under the racketeering statutes.

On June 14, 1995, Shadur called Bailey to make a final statement. The con man said he was sorry for cheating the women in his horse deals but repeated that he had nothing to do with Brach’s disappearance.

“I know my sentence could be reduced if I furnished truthful information regarding Helen’s disappearance, but I don’t have any,” he said. “I wish I did.”

Shadur said Katz’s testimony tipped the balance between Miller’s shaky witnesses and Bailey’s lies and seeming unwillingness to admit wrongdoing.

If Bailey had shown remorse, Shadur said, he would have been content to lock him up for 10 years.

Shadur concluded it was “more probable than not that Bailey did commit the offenses of conspiring to murder and soliciting the murder of Helen Brach. That calls for a sentence of life imprisonment.”

Tuite argued Shadur could not impose a life sentence because of the federal sentencing guidelines in place when Brach disappeared. Two days later, Shadur relented and changed the term to 30 years — 10 years for the horse frauds and another 20 for the Brach conspiracy, with a possible release from prison after 25 years, by which time Bailey would have passed his 90th birthday.

Bailey’s punishment was tantamount to a life sentence for a crime for which he had technically never been convicted.

The court of appeals upheld Shadur’s sentence.

Richard Bailey, who had once described Helen Brach as the “goose that laid the golden egg,” was going to prison, his own goose very much cooked.

About the author: James Ylisela Jr. is a longtime Chicago journalist and teacher. He has written for the Chicago Sun-Times and Chicago Tribune and been a contributing writer to Chicago magazine. He taught journalism in the graduate school at Northwestern University’s Medill School for 13 years.

James Ylisela Jr.