Waukegan chief of staff brings federal experience to City Hall; ‘I was kind of like the Swiss army knife'

Chicago Tribune

2 days ago

Joshua May started working when he was young, took an interest in politics as a field organizer in former State Sen. Melinda Bush's, D-Grayslake, 2016 campaign and worked for several state and federal officials the next four years, including U.S. Rep. Brad Schneider, D-Highland Park.
Making his home in Waukegan in 2019 while holding his political jobs, May eventually became chief of staff for U.S. Rep. Bob Morgan, D-Deerfield. In early 2021, an opportunity took him from Waukegan to Washington, D.C., where he joined President Joe Biden's administration.
Starting in the U.S. Office of Management and Budget, May became deputy chief of staff in the department for over a year until his job ended on Jan. 20, 2025, as Biden left office at the end of his term. He then chose to return to Waukegan, where he will ply his skills for Mayor Sam Cunningham.
May started his job as Cunningham's chief of staff last week at City Hall in Waukegan excited to be back in the hometown of his adulthood and ready to use experience acquired at the highest level of government to help the mayor fulfill his vision for the city he started leading again on May 5.
Rejecting the idea of becoming a lobbyist in Washington, May said he wanted to go somewhere and do something where he could use the experience he gained in the White House to have a positive impact on people's lives.
'Waukegan's got a place in my heart,' May said. 'The city has a lot of good potential with the lakefront, the harbor and a downtown becoming relevant again. It's a melting pot for Lake County and Illinois.'
Initially his responsibilities in the Biden administration were personnel-related. He learned to understand human resources skills, and said he developed a knack for working with people which he intends to transfer to the Waukegan mayor's office. His responsibilities were multifaceted.
'I was kind of like the Swiss army knife,' May said. 'I learned process and people management. When you know the process, you can understand and distill complex issues. That's how you build (effectiveness) in City Hall with more than 500 employees, to help them be most effective for the taxpayers. They have to understand we're all in this together.'
Understanding May's ties to the area, knowing he worked for Schneider and learning what he did in Washington, Cunningham said he reached out to him about the chief of staff job. May offered his help to the incoming mayor.
'He brings to the city experience at multiple levels of government,' Cunningham said. 'I will need assistance like that in the mission I'm undertaking to rebuild Waukegan. He understands we are a melting pot. From his time in the White House, he understands serving people.'
Schneider said in an email he watched May grow from a staff assistant in his Lincolnshire congressional office to his campaign's political director, and then 'serving the most senior levels of our government in the Biden administration.'
It 'is a testament to his unwavering dedication to public service and deep understanding of how government can improve lives,' Schneider said. 'I know he'll bring both heart and strategic vision to the role. I look forward to partnering with them, both as they work to build a brighter future for Waukegan.'
Growing up in Chicago's Rogers Park neighborhood as a youngster, May said his family moved to the Deerfield area when it was time to start middle school. He graduated from Adlai E. Stevenson High School in 2009.
Spending two years at the College of Lake County between 2011 and 2013, May went to work full-time. After helping Bush get elected in 2016, he became a staff assistant for Schneider, eventually becoming the political director for the congressman's 2018 reelection campaign.