For decades, two families worked hand-in-hand as the top political powerhouses in Chicago.
The Daley name is still synonymous with Chicago politics.
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And while the name Dan Ryan might remind more Chicagoans of their daily commute than their political history, the former Cook County board president teamed with former Mayor Richard J. Daley for years to pave the way for the expressway that became his namesake.
So it came as a “shock and disappointment” to Daniel B. Ryan III on Friday when Bill Daley — the son of Chicago’s legendary boss — proposed removing his grandfather’s name from the highway after 56 years and renaming it in honor of former President Barack Obama.
The Dan Ryan Expressway looking north from 31st Street, several months before construction was completed in December 1962. | Sun-Times file photo
The Dan Ryan Expressway looking north from 31st Street, several months before construction was completed in December 1962. | Sun-Times file photo
“I’m hurt. I feel bad that he didn’t try and contact us to see what we would think,” Ryan III said. “We feel very honored to have this named after our grandfather. Why would you take an honor away from one man to honor another?”
In his quest to become the third Daley to reign on the fifth floor of City Hall, Daley issued a press release saying “Chicago expressways are named for towering figures in out history: Kennedy, Eisenhower, Stevenson,” suggesting the 11.5-mile stretch of Interstate 90/94 should instead be named for Obama.
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The campaign statement noted that the namesake Ryan was a longtime Cook County board member and its president from 1954 to 1961, pointing out “that a forest preserve is also named for Ryan.”
Bill Daley
Mayoral hopeful Bill Daley. | Rich Hein / Sun-Times
What the campaign didn’t mention is that Daley’s father was the one who chose the Dan Ryan Expressway name in the first place, according to Ryan III. It also was incorrect in its assertion about the forest preserve. The Dan Ryan Woods aren’t named for the same person as the highway; they’re named for Dan Ryan’s father, who also had a career in Chicago politics. 
The Ryan family was a political dynasty in its own right when Dan Ryan took his late father’s position on the county board in 1923. Three decades later, as board president, Ryan was considered second in power only to Boss Daley himself.
Ryan helped lead the fight for a “superhighway” connecting interstates 90 and 94, but died unexpectedly in 1961. The expressway opened about 18 months later, on December 15, 1962.
Mayor Richard J. Daley (left) and Cook County Board President Dan Ryan (center) look at a concept model of a downtown development in September 1958. | Sun-Times file photo
Mayor Richard J. Daley (left) and Cook County Board President Dan Ryan (center) look at a concept model of a downtown development in September 1958. | Sun-Times file photo
For his widow Ruby Ryan — who was appointed to her late husband’s board seat with Daley’s support, and went on to serve for two decades — the expressway title proved a fitting tribute.
“It will run right past the home where he grew up, at 66th and Stewart,” his wife, Ruby Ryan, was quoted as saying in the front-page Sun-Times story about the newly christened highway.
Cook County Commissioner Ruby Ryan, Mayor Richard J. Daley and county board President Seymour Simon congratulate Theresa Waicosky, a Back of the Yards resident who became the first person to drive on the Dan Ryan Expressway at its December 1962 opening. | Sun-Times file photo
Cook County Commissioner Ruby Ryan, Mayor Richard J. Daley and county board President Seymour Simon congratulate Theresa Waicosky, a Back of the Yards resident who became the first person to drive on the Dan Ryan Expressway at its December 1962 opening. | Sun-Times file photo
Ryan III recalled finishing a high school entrance exam and then hurrying downtown to meet his grandmother for the expressway ribbon-cutting.
“It would’ve meant a lot to him to know it was named for him. That was a true honor bestowed on him for all the work he did. It was the culmination of a great career,” Ryan III said Friday.
The Dan Ryan's opening was front-page news for the Sun-Times in December 1962, framed here with the scissors and a strip from the ceremonial ribbon-cutting. | Provided by Dan Ryan III
The Dan Ryan’s opening was front-page news for the Sun-Times in December 1962, framed here with the scissors and a strip from the ceremonial ribbon-cutting. | Provided by Dan Ryan III
“These families stood together for many years. I guess it’s been forgotten,” said Tara Ryan, the expressway namesake’s great-granddaughter.
A Daley campaign spokesman declined to comment on the Ryan family’s reaction.
Beyond political business, Ryan III said his grandfather and Richard J. Daley were good friends. He remembers the families taking in a 1959 White Sox World Series game together at Comiskey Park, and working alongside Bill Daley as pages at Chicago’s notorious 1968 Democratic National Convention, he said.
Cook County President Dan Ryan (front left) and Mayor Richard J. Daley (with mitt) attend Opening Day at Comiskey Park in April 1958. | Sun-Times file photo
Cook County President Dan Ryan (front left) and Mayor Richard J. Daley (with mitt) attend Opening Day at Comiskey Park in April 1958. | Sun-Times file photo
“We did a lot of things together. We were old friends,” he said.
Since then, “everybody’s gone their ways,” according to Ryan III, age 69, now retired after a career in insurance. He suspects the renaming idea is a vote-getting tactic.
Ryan III insists he’s an Obama fan. “But you don’t change something just to change it.”
Three generations of Dan Ryan today; from left to right: Ryan III, Ryan V and Ryan IV. | Family photo
Less clear is whether the state legislature would get behind Daley’s proposal, especially after a stretch of Interstate 55 already was named after Obama last year.
“And I don’t think President Obama would ever want someone else’s honors and accomplishments to be taken away for him,” Tara Ryan said.
Representatives for the 44th president did not return messages seeking comment.
“I don’t want this to sounds like sour grapes,” Ryan III said. “Our family has been honored by this for 56 years, and we’d like to keep it that way.”
Dan Ryan Woods
The Dan Ryan Woods, part of the Cook County Forest Preserves, stretch from 83rd Street south to about 93rd Street, between Western and Damen avenues. | File photo