Bill Daley announced his decision to run for mayor of Chicago, continuing a Daley family dynasty in the city.

Daley is the son of Richard J. Daley and the brother of Richard M. Daley, who remain Chicago’s two longest-serving mayors, 21 and 22 years, respectively.

“Daley’s last name, by itself, boosts him into the circle of six-to-eight candidates who likely will gather sufficient petition signatures to get on the February ballot,” communications instructor John McCarron said. “Don’t forget that the Southwest Side Irish/white-ethnic machine-within-the-Machine essentially ran politics hereabouts for almost 50 years.”

Aside from family ties to local government, Daley is no stranger to politics, having served as White House chief of staff to former president Barack Obama from January 2011 to January 2012. Daley additionally served as U.S. Secretary of Commerce from 1997 to 2000 under former president Bill Clinton. “I think he is certainly very passionate about Chicago and public service,” said professor Nick Kachiroubas. “He always struck me as being willing to talk in those situations about reflecting about what he’s done and looking at it as a multifaceted point of view.”

Daley previously ran for the state’s top officer in 2013 against then-governor Pat Quinn in the Democratic primary. Daley subsequently left the race, stating that he was not prepared for the magnitude of the campaign. Daley said he would never run for office again.

Daley explained the motivation behind his campaign in a Sept. 18 radio interview with WBEZ on their show “Morning Shift.”

“When I flirted with the idea of running for governor, it was a little foreign to me quite frankly” Daley told WBEZ. “You had an incumbent governor, a Democrat, somebody who had lots of difficulties and I thought was damaged and probably couldn’t win, and didn’t. And we ended up with Republican Gov. Bruce Rauner, who’s had a dismal record for four years.”

Daley went on to say that while he felt he could not make a significant difference during his campaign for governor leading to him eventually dropping from the campaign, he is confident in his mayoral campaign.

While the Daley legacy is certainly important to Chicago politics, some worry that it could be a potential deterrent to Daley’s campaign.

The legacy of Richard J. Daley is especially complicated, particularly his handling of the 1968 Chicago riots. The former mayor had infamously ordered “shoot to kill arsonists” and “shoot to maim looters,” creating a controversy throughout the city.

Despite the controversy surrounding his remarks during the riots, Richard J. Daley was the chairman of the Cook County Democratic Central Committee for 23 years after the riots and continues to remain an icon within Chicago and its political sphere.

“Daley brings instant name recognition but the family dynasty is a mixed legacy,” said Chris Bury, senior journalist in residence at DePaul. “Richard M. Daley served 22 years and was a popular mayor, but he left the city in terrible financial shape and his deal to sell Chicago’s parking meters was a disaster. Daley’s father dominated Chicago politics in a different era of machine politics.”

Bury believes that the road will be hard for Daley to break away from his family’s political legacy and create a name for himself in the upcoming elections.

“Bill Daley will have to show what sets him apart in a city that is very different from the one his brother and father led,” Bury said. “Chicago is now much more diverse and racially and ethnically divided than it was even a few years ago.”

In the interview with WBEZ, Daley expressed interest in not having his campaign conflated with the legacy of his father and brother.

“Some people liked [Richard M. Daley] and thought his tenure was great. Others said it was terrible,” Daley said. “So I’ll let the voters decide—hopefully not about Richard M. or Richard J., but about Bill Daley. Because we are different.”

Aside from being a big name within Chicago, the Daley family also holds ties to DePaul. Both Richard J. and Richard M. Daley graduated from the College of Law. The Daley Building at 14 E. Jackson Blvd. is even named after the younger mayor and his wife, Maggie.

“I think DePaul had a very important place in both [Richard J. Daley’s and Richard M. Daley’s] educational careers.” Kachiroubas said. “I think Bill Daley would have a closer tie to Loyola, but he’s certainly been good to DePaul as he’s been willing at speak to DePaul in years past.”

While Daley is an experienced politician, his ability to run his own campaign has been questioned, especially following his failed campaign run in 2013.

“Just about everyone in the media knows Bill Daley from his longtime career as a corporate executive, his service in the Clinton and Obama administrations, and his on-again/off-again runs for the governor’s office,” McCarron said. “Those first two gigs are biographical assets. His cancelled feints toward the governor’s office leave some thinking he’s not in this one for the long haul.” Daley’s age and potential lack of a connection with voters are another potential obstacle he will face during his campaign.

“Can he connect on a personal level with voters? Does he have a vision for Chicago that resonates? Can a 70-year-old white business guy appeal to a younger and more diverse city population?” Bury said. “These are questions that can only be answered as the campaign unfolds.”