Ray Kest wasn't the first high-profile Toledoan to bear that name. That was his grandfather, a Blade circulation director, charity co-founder, and larger-than-life figure in Toledo for much of the 20th century.
Raphael “Ray” Kest came to Toledo in 1906 as a 5-year-old from Latvia, a northeastern European country about half the size of Ohio. His father hawked The Toledo Blade on street corners to help his Jewish immigrant family of seven make ends meet.
By age 7, Ray started selling The Blade too. It was an era when “newsboys,” no matter how young, fought over their sales turf. While Ray was considered a lightweight, he learned to fight well and hold his ground.
His Blade bosses saw an aggressive, street-smart kid whom they groomed for leadership in the rough-and-tumble circulation wars of Toledo - a time when publishers used circulation workers as muscle to keep newsboys in line while battling competing newspapers for prime selling spots.
By 1944, Ray had risen to become the newspaper's circulation director, where he earned the respect of his underlings - at least those who followed the rules.
“He was a very honest, very good man,” recalled Robert Brandon, retired Blade marketing manager who was a district circulation manager under Ray.
“All he asked out of you was a good day's work. You did your job, and you never had any trouble with Ray,” Mr. Brandon said.
Added Hildegarde Condon, a former circulation service supervisor: “He was a super boss. ... He didn't play games with people, and he'd do anything for anybody.”
Newsboys remember Ray as a gruff, father-like figure with a soft heart. He tried to ensure that they were treated fairly by low-level circulation employees, who often tried to cheat the newsboys out of money by claiming the newsboys had been given more papers to sell than they had.
Former newsboy Julius Boxenbaum recalls that Ray often gave rides to the children - many like Mr. Boxenbaum - who were so poor they had holes in their shoes.
“Ray was good to the kids. They liked to sell for him,” Mr. Boxenbaum said.
In the heights of the Depression, Ray began a personal crusade to provide for the less fortunate - particularly children - through a group he co-founded, Old Newsboys Goodfellows Association.
He used his contacts throughout Toledo to marshal help for anyone in need. It was a philosophy of help first, ask questions later. He was known to call all kinds of associates, at all hours of the day, to line up food, clothing, or coal for those in need.
Retired reporter John Grigsby recalled that Ray hung around the newsroom, waiting for reporters to return from scenes of tragedies. “You'd come back to the office and Ray would say, `Do they need help?' You'd say yes and he'd be out the door, bringing them a voucher or taking them to get some food or what they needed,” Mr. Grigsby said.
Ray also became a trusted adviser to then-Blade publisher Paul Block, Jr., who took over running the paper in 1942. Mr. Block named him to the company's board of directors.
“Ray was really a right-hand man to Paul Block, Jr.,” said retired Blade reporter Seymour Rothman.
Ray associated with politicians, judges, and business owners - often holding court in a downtown bar, said Ben Illman, a retired accountant and former newsboy. He oversaw the city's boxing commission for years and hobnobbed with entertainers who passed through town.
Ray was seen as an emissary to Toledo's underworld as well.
He had grown up associating with such gangsters as the late gambling kingpin Leonard “Chalky Red” Yaranowsky and Licavoli gang front-man Jacob “Firetop” Sulkin.
Ray helped fight to get a death sentence commuted for Sulkin, a former newsboy, for plotting the Licavoli gang's 1933 murder of local bootlegger and street hero Jack Kennedy.
Ray's association with local organized crime earned him a spot in the controversial tell-all crime book Unholy Toledo, written by Mr. Illman's brother, Harry, a disbarred lawyer.
Harry Illman, who died last week at age 82, wrote of Ray's toughness and willingness to enlist organized crime to help him in his job. The book alleged that Ray ensured that local organized crime figures got “good press” and, in return, organized crime ensured that those under their control bought plenty of the charity editions printed by the Old Newsboys.
“He had a ready-made list of contributors each Christmas that enabled him to bring in top dollar without too much effort,” Harry Illman wrote in the book.
Mr. Rothman, like other former employees, said he was not sure how deeply connected Ray was to the city's organized crime.
But he said it was clear that the city's underworld looked to him as a conduit to Mr. Block.
After federal and local officials formally shut down local gambling operations in the 1950s, many of the gamblers turned to Ray to see whether the newspaper would allow the industry to quietly be restored.
“After things quieted down, they went to Ray, and Ray went to Paul, and Paul said no,” Mr. Rothman said.
During his tenure as circulation director, Ray was regarded as one of the most influential and revered Toledoans of that time, said friends and co-workers.
“He was very active, mostly for the kids, and he knew a lot of political people,” said Mr. Boxenbaum, who is now the president of the Old Newsboys.
Ray died in 1964, at age 63, of cancer. His grandson Ray was 14 then. It would be 11 years before the name Ray Kest would appear on the ballot.
“He was just a wonderful guy,” said the grandson Ray Kest.
“I've had some people say to me, `What about your grandfather's shaky past [referring to Unholy Toledo]?' And I say, `You know what, I'm proud of my grandfather,'” Mr. Kest said. “If the worst crime was that he associated with people who ran booze, give me a break. It was a different era, and people had to make a buck.”