As the DNC returns to Chicago, Illinois’ dean of the delegation, Dick Durbin, basks in the moment.

As Chicago prepares to host the Democratic National Convention, U.S. Sen. Dick Durbin is somewhere on the back end of a distinguished career with a big, unsettled question looming about his political future.

The dean of Illinois’ congressional delegation turns 80 this fall and is in a much different spot politically — and in life — than when Chicago was last a convention city for Democrats and he was immersed in his first U.S. Senate campaign.

Back then, Illinois Democrats gave Durbin the ceremonial task of awarding the state’s delegates to President Bill Clinton from the same United Center floor where months earlier Michael Jordan had won his fourth NBA title.

“In Illinois, this land of skyscrapers and cornfields, we’re proud of the traditions of our families and Midwestern values,” he said in a convention floor speech, his political mentor, retiring U.S. Sen. Paul Simon, standing alongside him.

The Jordan magic rubbed off on Durbin, who went on to win his election that year in a 15-percentage-point trouncing.

Almost three decades later, he looks back at that 1996 convention and remembers the “honor,” as a little-known downstate congressman, of being embraced by Illinois Democrats as chair of the state delegation. He remembers how pitch-perfect weather gave the city a glorious, travel-brochure patina. And he recalls how that year’s convention was also haunted by the ghosts of Chicago’s Democratic convention of 1968.

“I was praying to God we had nothing like it,” Durbin said. “We didn’t.”

As this convention approaches, Durbin is in a reflective phase of his career, not at a moment of political ascension.

Sen. Dick Durbin sits for a portrait at his office at 230 South Dearborn in Downtown Chicago on July 16, 2024.

Manuel Martinez/WBEZ

With a career stretching across seven decades of Illinois politics, Durbin has been in the room — and in the car — with everyone from revered Senators Paul Douglas, Paul Simon and Barack Obama to now reviled former House Speaker Michael Madigan. He even knows why Madigan famously ate nothing but a sliced apple for lunch every day.

There is no shortage of Democrats parsing Durbin’s every move, trying to suss out if this term might be it for the No. 2-ranking Democrat in the U.S. Senate. He has this advice for those already quietly jockeying for his job in 2026: Cool your heels.

“I’ll make up my mind and decide whether I’m going forward or not after the first of the year, and people on the bench then have to make decisions accordingly,” Durbin told WBEZ from his Chicago office overlooking the Loop and Lake Michigan. If Durbin serves out the remainder of his term, which would end Jan. 3, 2027, he’d be the longest serving U.S. senator in Illinois history.

Durbin wouldn’t say whether he eventually wants a hand in picking a successor from a stable of congressional or statewide officeholders, and it’s not clear he has an established favorite if he opts to retire. On that “bench,” he said, are people like Lt. Gov. Juliana Stratton or Illinois Treasurer Mike Frerichs, whom Durbin said either he or his wife assisted early in their political careers.

Durbin underwent hip replacement surgery in June and knee replacement surgery last October. He’s back on his feet, but his voice is noticeably gentler than it has been in the past. He appears razor-sharp mentally, describing himself as being “in good shape.”

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Questions about age and mental acuity caused President Joe Biden to end his re-election bid. Unlike some of his Illinois congressional colleagues, Durbin did not call on Biden, a friend of 30 years, to step aside.

Durbin said he never has been an advocate for placing an upper age limit on public service, and it appears he is applying the same standard to himself. He acknowledges his ongoing work in the Senate still feels “fresh” to him.

“If we’re going to be fair, we should judge individuals on their own performance,” he said.

Douglas, Simon and their influence

On Durbin’s desk when he met with WBEZ was a yellow, worn copy of a Chicago Tribune Magazine from 1973. In it was Simon’s first-person account of how he set out to better understand the “Lincolnesque” legacy of his own political guiding light, former Democratic U.S. Sen. Paul Douglas, who served between 1949 and 1967.

Dick Durbin (center), then-Sen. Paul Simon and then-Sen. Carol Moseley Braun share a laugh at Manny’s Deli on March 18, 1996 during Durbin’s run for U.S. Senate.

Robert A. Davis/Sun-Times

The Tribune magazine piece shows Simon’s presence is never far away from Durbin despite the former senator’s death in 2003, and it’s an example of the through-line that exists from Douglas to Simon to, now, Durbin.

“In the Senate,” Simon wrote of Douglas in the Tribune piece, “this ex-Marine headed the fight for civil rights long before it was fashionable, for higher ethical standards long before a Watergate could have been imagined. He pioneered unpopular causes and helped to create the climate that would later see passage of bills requiring disclosure of interest rates and other consumer protective measures.

“In more than 20 years of close observation of Douglas,” Simon continued, “I have never seen him even hint at doing anything unethical.”

Durbin credits Douglas with giving him his first real taste of politics. It came during Douglas’ 1966 U.S. Senate re-election bid in southern Illinois. Durbin was in his mid-20s and still far removed from his own first winning congressional election in 1982.

“Douglas asked me to work on his campaign, and I met Paul Simon for the first time. /It was West Frankfort, Illinois, going store to store, door to door, passing out brochures for Douglas. And we took a liking to one another,” Durbin said of Simon.

The two kept in touch after Douglas lost that race. And when Simon was Illinois lieutenant governor, he hired Durbin to work in his office. As a boss, Simon required his staff to fill out financial disclosure forms that showed “every dollar that you own.” It was a far more stringent disclosure requirement than anything else in state government at the time.

Having just finished law school, Durbin said he carried thousands of dollars in student loan and medical debt, and the required disclosure was “embarrassing to me…The first net worth that I disclosed showed me ready for bankruptcy.”

Still, Durbin said it represented the most valuable and enduring lesson Simon passed on to him about public service.

“Honesty, above all. It probably was natural to him as a son of a Lutheran minister. But he got it from Paul Douglas, who wrote the book on ethics and government,” Durbin said. “It set a standard of don’t expect to get rich if you’re going to be in politics because if you do, you’re going to get in trouble.”

The federal corruption cases against former Chicago Ald. Edward Burke and Madigan arguably dramatize the hazard of mixing politics and business. Madigan awaits trial on racketeering, bribery and conspiracy charges, while Burke was convicted of racketeering, bribery and extortion.

Both men had lucrative careers as property tax appeal attorneys that factored into the criminal cases against them.

“The people who are engaged in it are as political as anybody on this earth, trying to get the best valuation for their clients. And when it came to Madigan, he tried to combine that, as Ed Burke did, too, with public life, and I think that caught up with them, both of them,” Durbin said.

Pre-indictment, Durbin characterized his relationship with Madigan as good but not close.

The only time Durbin remembered having a personal conversation with Madigan came when the former speaker once offered to drive him from Springfield to Chicago.

“Just the two of us in a car for 3 ½ hours. Talked about a lot of things. You know, he talked about his family. He talked about the fact that when he was in the…constitutional convention, he was overweight, [that] he was going to lose weight,” Durbin said, alluding to the 1970 confab that drafted a new state constitution. “And then that apple for lunch program came to be.”

During his days in Springfield, Madigan notoriously skipped lunch, aside from a carefully pared apple.

Durbin’s legislative mark

Durbin’s main residence remains in Springfield, where he lives with his long-time wife, Loretta. They have a home on a well-manicured, tree-lined street near the city’s main park, but it would not rank among the capital city’s most expensive real estate listings. He generally makes about 50 round-trips per year between Washington and Illinois. Until the pandemic, he maintained a folksy, Sunday morning tradition in which he invited journalists to his Springfield residence to outline his Senate work and talk about news events of the day.

Durbin has major legislative fires he continues to stoke, including pursuing ethics reforms for the U.S. Supreme Court where Justices Samuel Alito and Clarence Thomas have faced criticism over their acceptance of undisclosed trips from billionaire GOP donors.

He has taken aim at the banking industry for excessive fees passed along to businesses and consumers on credit card transactions. And he is pushing for tighter oversight over airline carriers and their use of credit cards linked to their frequent-flier programs.

As chair of the Senate Judiciary Committee, Durbin oversaw the confirmation of Supreme Court Justice Ketanji Brown Jackson, the first Black woman to serve on the nation’s highest court.

He was the earliest of backers in the U.S. Senate for Barack Obama’s 2008 bid to become president, helped elevate current U.S. Sen. Tammy Duckworth into Obama’s old seat, and has spearheaded efforts to allow undocumented immigrants who grew up in the U.S. a pathway to citizenship.

With Obama, Durbin said he still communicates with the former president, but their relationship is different than it once was.

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“It’s good, but it’s not as close as I want it to be because he spends a good part of the year in Hawaii and another part of the year up in … Martha’s Vineyard. … He’s gone with his family as I would be too in his circumstance. But he called me the other day. We had a good conversation and promised lunch soon. So, I really respect him.”

Asked what his No. 1 accomplishment at the Capitol was, Durbin pointed to his push as a congressman to ban smoking on domestic airline flights, a Reagan-era law opposed by the tobacco industry that first put Durbin on the political map in Illinois.

It was a personal issue for him. His father died at age 53 of lung cancer caused by years of chronic smoking. The legislation wasn’t easy to pass, but it was an important milepost in stamping out public smoking.

“People kind of stepped back and said the obvious: ‘Wait a minute, if this isn’t safe on an airplane, why is it safe in a train, or a bus, or a hospital or office building?’ And then, the next thing you know, the dominoes started tumbling, and we took all the smoking away in most circumstances,” he said.

Co-chairs of the Senate Ukraine caucus Senate Majority Whip Dick Durbin, D-Ill., right, and Sen. Roger Wicker, R-Miss., talk during a meeting with Ruslan Stefanchuk, speaker of the Parliament of Ukraine, not pictured, in the Capitol on Tuesday, July 9, 2024, in Washington.

Kevin Wolf/AP Photos

As Durbin looks ahead to the fall campaign, he sees a close election. He quickly endorsed Vice President Kamala Harris when Biden left the presidential race, describing her as a “critical partner in building the Biden record.”

“Count me in with Kamala Harris for president,” Durbin said.

If Trump prevails, Durbin said he holds out hope for developing some kind of working relationship with a Trump White House, just as he did on at least one occasion during Trump’s previous term. In 2018, Durbin was a key part of a bi-partisan push to pass a major criminal justice omnibus called the “First Step Act,” which Trump signed into law.

“I never would have dreamed that I would have put together a significant piece of legislation like that, and that he would sign it into law. And he did. So I don’t rule out the possibility of working with him if he’s reelected,” Durbin said of Trump. “There may be an opportunity.”

Staying on the job through the next president’s full term remains an open question for Durbin. But that uncertainty hasn’t stopped him from pondering his mark on Illinois politics over seven decades — and the help he got along the way.

“I remember Paul Simon. I said, ‘Why do you do all this income disclosure and ethical stuff?’ He said, ‘I want people, even if they disagree with my vote and think I’m completely stupid, to believe I’m honest, [that] I did it for the right reasons,’” Durbin said. “I guess the first thing you should hope for is that people respect you for your honesty — issue honesty and dollar honesty. And that’s the starting point.”

Dave McKinney covers Illinois politics for WBEZ and was the longtime Springfield bureau chief for the Chicago Sun-Times. He covered Durbin’s first U.S. Senate campaign.

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