In the summer of 2003, as Martha Stewart’s trial on charges connected to securities fraud was nearing its conclusion, the CNN news anchor Anderson Cooper aired a segment speculating about how severe her punishment would be if she were convicted.
“Sometimes,” Mr. Cooper said, “it seems as though rich criminals seldom end up swapping smokes on Cell Block H. So if it’s not hard time in the joint, what kind of sentence could she get?”
His guest was Herbert Hoelter, a sentencing reform advocate who, to fund his nonprofit work at the National Center on Institutions and Alternatives, had become a concierge to the federal prison system for white-collar criminals, helping them to secure alternative or shorter sentences and to navigate life as an inmate.
“Our philosophy isn’t that punishment should not occur,” Mr. Hoelter said, “it’s that it should occur in different ways.”
Mr. Hoelter died on May 2 in Baltimore, not far from his home in Catonsville, Md. He was 73.
His daughter Katie Hoelter said the cause of his death, in a hospital, was complications of congestive heart failure and DRESS syndrome, a rare hypersensitive reaction to certain medications.
Mr. Hoelter’s client list was a Who’s Who of corporate and financial scandal, including Leona Helmsley, the hotel baroness convicted of tax evasion; Bernard L. Madoff, the architect of the largest Ponzi scheme in financial history; Ivan F. Boesky, the financier convicted of insider trading; Michael R. Milken, the so-called junk bond king; and, after she was convicted, Ms. Stewart.
Mr. Hoelter’s main role in these cases was writing lengthy biographies of his clients — to help them appear sympathetic to judges, and to offer possibilities for alternative or lesser sentences.
“One of Herb’s best qualities was that he was able to humanize those who were about to be sentenced,” Richard J. Schaeffer, a New York lawyer who regularly consulted with Mr. Hoelter, said in an interview. “Many of these people felt they had given much more to society than others would have believed, and that they still had more to offer.”
When he worked for Ms. Stewart, Mr. Hoelter argued that her conviction, on charges that she lied about why she had sold shares of a biotechnology company, had already severely damaged her reputation. (The judge threw out a securities fraud charge during the trial.) Her legal team also presented an alternative to prison time: teaching disadvantaged women how to start their own businesses. The judge sent her to prison anyway, but for only five months, well short of what prosecutors wanted.
Mr. Hoelter also collected copious statistics on sentencing patterns to help sway judges.
After Mr. Milken was sentenced to 10 years in prison, his lawyers hired Mr. Hoelter, who produced data showing that the sentence was tougher than what others had received after being convicted of similar charges. His legal team also argued that Mr. Milken had been a role model in prison, tutoring other inmates, and could continue that work near his home in Los Angeles. A judge reduced Mr. Milken’s sentence to two years, plus three years of community service.
Thousands of lesser-known white-collar criminals also benefited from Mr. Hoelter’s counsel.
“Our whole philosophy is that one should pay back the community, either in terms of financial restitution and/or social restitution,” he told Mr. Cooper on CNN. “I mean, we’ve had construction magnates build wings of hospitals for kids with spina bifida. We’ve had food executives create large amounts of food coming into food banks. There’s wonderful creative ideas that one can fashion that judges should look at, as well as the background of the different individuals that are there that come before them for sentencing.”
Herbert Joseph Hoelter Jr. was born on Sept. 20, 1950, in Yonkers, N.Y., and grew up in Niagara Falls. His father was a county official. His mother, Helen (Parker) Hoelter, managed the household.
Growing up, he worked part time in a doughnut shop and delivered newspapers. He was also a volunteer coach of a youth basketball team with a roster of players from troubled homes.
One weekend, only two of the 10 players showed up; the others had been arrested and taken to a juvenile detention center.
“So he goes to the place to see what he can do,” his daughter Katie said. “He was so distraught at the conditions they were in. It broke his heart and opened his eyes to the terrible things going on in the juvenile detention system.”
After graduating from the State University of New York at Buffalo (now the University at Buffalo) in 1972 with a bachelor’s degree in English, Mr. Hoelter earned a master’s degree in social work from Marywood University in Scranton, Pa., where he began counseling juvenile defenders.
In 1977, he founded the National Center on Institutions and Alternatives in Baltimore with Jerome G. Miller, a juvenile justice reformer who had almost single-handedly closed reformatories in Massachusetts in the early 1970s.
The next year, a doctor who had been convicted of federal tax charges called Mr. Hoelter and asked, “Could you do an alternative sentence for me?”
“So we put together an alternative sentence where he would help an AIDS clinic for free for 500 hours rather than go do laundry at a federal prison, and the judge liked it,” Mr. Hoelter said in a 2016 interview with a business publication in Baltimore. “That sprang into doing more cases like that.”
For decades, Mr. Hoelter poured the fees he generated from white-collar clients back into his organization.
“That money wasn’t going into his pocket,” Vincent N. Schiraldi, the secretary of juvenile services for the State of Maryland, said in an interview. “He was plowing that money into doing sentencing reports for poor people.”
Mr. Hoelter married Susan Marie O’Keefe in 1969. She died in 2000. He married Martha Jane Ginn in 2002.
In addition to his daughter Katie, his wife survives him, as do another daughter, Sarah Coble; a son, Jeffrey; his sisters, Joan Castellani, Melanie Hoelter and Moria Saviola; a brother, Peter Hoelter; and 10 grandchildren.
After Mr. Hoelter’s clients were sentenced, he counseled them about life in prison. He told them to make their time meaningful: teach adult education classes, exercise, read a lot. If he had another client in the same prison, he made sure they looked out for each other.
More than anything, he was a friendly, impartial sounding board.
Katie Hoelter remembers answering the phone early on Christmas morning in 1992, the year she turned 7.
Picking up the receiver, she assumed that a family member would be on the other end. Instead, it was a collect call from a prison inmate — Ms. Helmsley.
“Merry Christmas,” Katie said, after accepting the charges.
Ms. Helmsley, known as “the Queen of Mean” in the tabloids, wasn’t in a festive mood.
“I don’t care what day it is,” she said. “Let me talk to your father.”
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