The Recombobulation Area is a 19-time 21-TIME! Milwaukee Press Club award-winning opinion column and online publication founded by Milwaukee journalist Dan Shafer.
The Recombobulation Area launched in the latter months of 2019, and one of the first elections we covered at the publication was the race for Milwaukee County Executive in the spring of 2020.
That election featured a 33-year-old upstart politician by the name of David Crowley. Crowley was in his second term in the state legislature, representing the 17th Assembly District — which included neighborhoods on the west and northwest side of the city of Milwaukee — and he was quickly getting to work, becoming the chair of the Legislative Black Caucus and of the Milwaukee Democratic Legislative Caucus.
When then-Milwaukee County Executive Chris Abele announced in November of 2019 that he would not be seeking re-election after serving in the role since 2011, Crowley was one of several candidates to announce a bid for the office.
That field was narrowed before the February primary — with echoes of that race in Crowley’s recent victory — and around that time, I interviewed the three top candidates for the office for a piece on the race. Along with Crowley, those candidates were State Sen. Chris Larson and then-County Board chair Theodore Lipscomb.
After that series of interviews, I chose to endorse Crowley in the race, writing, “Milwaukee needs a bridge-builder. The County needs someone with a progressive vision to pair with the type of leadership needed to affect real change.” That sure is what we’ve ended up getting here in Milwaukee County under Crowley’s leadership.
Crowley would go on to win a narrow victory over Larson in that race in the spring of 2020, was re-elected running virtually unopposed in 2024, and now, is the Democratic nominee in the race for governor here in 2026.
Our time covering news and politics in Milwaukee and Wisconsin has overlapped quite a bit with David Crowley’s rise from state legislator to County Executive to Democratic nominee. From coverage of campaigns and elections to the landmark legislative achievement of Act 12 to several one-on-one interviews over the years — including a live event with Crowley back in 2022 at Anodyne Coffee’s Walker’s Point Roastery, which was filmed by and broadcast at CW18/My24 in Milwaukee — we sure have spent a whole lot of time covering David Crowley here at The Recombobulation Area. We were even the first publication to report on his interest in running for governor, during a Dec. 2023 interview.
So, while I’m away, here is a roundup of much of our Crowley coverage, from 2020 to 2026. We’ve organized this by year and embedded videos where possible.
Let’s recombobulate with our coverage of the person who could be Wisconsin’s next governor:
2020:
2021-2022:
2023:
2024-2025:
2026:
Dan Shafer is an independent journalist from Milwaukee who writes and publishes The Recombobulation Area. He worked with Civic Media from 2024 to 2026. He’s written for The New York Times, The Daily Beast, Heartland Signal, Belt Magazine, WisPolitics, and Milwaukee Record. He previously worked at Seattle Magazine, Seattle Business Magazine, the Milwaukee Business Journal, Milwaukee Magazine, and BizTimes Milwaukee. He’s won 24 Milwaukee Press Club Excellence in Journalism Awards. He’s on Twitter at @DanRShafer.
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Follow Dan Shafer on Twitter at @DanRShafer, at BlueSky at @danshafer.bsky.social, and on Threads at @danshafer.