Legislative Profile: Rep. Kalan Haywood II (D-Milwaukee)

February 06, 2020

District: 16th Assembly District – elected in 2018.
Personal: Born Milwaukee, WI, June 5, 1999; single. Attending Cardinal Stritch University (B.A. Business Administration)

It would be easy to focus on just one aspect of freshman State Assembly Rep. Kalan Haywood II and stop there: his age. Elected at age 19 to the Assembly in November 2018, Haywood is one of just three under-20s in the nation who won a state office race that cycle. And when he came to the Capitol to settle in, folks couldn’t resist grabbing a picture of Haywood with the state legislature’s oldest legislator: Sen. Fred Risser, who was 91 on Inauguration Day.
But when you sit down to talk with Haywood you quickly learn that his perspective is a bit more mature than that of the more typical college undergrad deciding whether to order dinner from Uber Eats or hop on a scooter and careen down the street to the campus hamburger joint. For example, prior to jumping into the 2018 race for an open State Assembly seat, Haywood did his homework.
“Before I ran for office, I actually called some of my colleagues into a meeting individually and said ‘Hey – I’m probably running for state rep. in this next cycle – what should I expect?’” Haywood explained recently in his State Capitol office. “And you know, the meetings went well – but they told me about 15% of what the experience is like around here, and the rest of the percent I experienced by myself.”
Haywood joined what turned out to be a five-person Democratic primary, besting the second-place finisher – the son of Congresswoman Gwen Moore – by 245 votes out of about 6,200 votes cast. He was unopposed in the general election, then hired another primary opponent to run his Capitol office. But no matter what the experience a candidate has before being elected, entering the State Capitol fray can be a jolt – perhaps especially when joining a caucus deeply mired in the minority: of the 99 seats in the State Assembly, Haywood is one of just 36 Democratic members.
“So the biggest surprise, truthfully, is how bad the partisan divide is,” Haywood said. “Some days it’s not that bad. Some days it’s non-existent, actually; some days we’re cool. But some days it gets a little messy and usually it’s not things we’ve done that we’re messy about – it’s things like ‘are we going to call it the Christmas tree or the Holiday tree’, you know?”
While a wide-ranging, unhurried conversation with Haywood shows how serious he is about important topics, there are still reminders that he’s firmly a member of Generation Z – such as describing his membership on the Assembly Committee on Veterans and Military Affairs as “super dope, because I come from a family of vets.” But while his vernacular can lean toward a more youthful side, a philosophical decision he faced soon after joining the Assembly revealed mature decision-making.
It’s perhaps simplistic, but a legislator in the minority deciding how to go about legislative business faces two general paths: one leads to being a partisan firebrand, believing that the role is to be a vocal and strident voice objecting to the majority party’s agenda. The other path is more low-key, and possibly more difficult: divining how to make legislative accomplishments by reaching out to the other side of the aisle to give input and seek support.
Haywood chose the latter path. When asked about his relationships with majority Republicans, he quickly listed numerous State Assembly leaders with whom he has built relationships, including the two most powerful members of the State Assembly: Assembly Speaker Robin Vos and Majority Leader Jim Steineke.
“So I try to keep relationships on the other side of the aisle because I think it’s super-important,” Haywood said. “Representative Steineke – definitely; we talk maybe once every couple weeks and the meetings are always good – they’re never tense meetings. I tell him what I’m working on and ask if he can help with it.
“I try to make sure we can bridge the divide and not polarize anybody,” Haywood said. “I want to make sure we’re bringing people together."
For Representative Steineke, his young colleague has shown to be someone he’s keeping an eye on.  
“For a new, up-and-coming member of the Assembly, I have to give Rep. Haywood a lot of credit for the thoughtful approach he brings to legislating,” Steineke said. “His willingness to reach out to folks from across the aisle is a standout reminder about how we can all work together in times of divided government.”
Haywood credits his age for that attitude.
“I came into office like ‘hey, let’s get some stuff done – how are we gonna get it done?” Haywood said. “I think that has got me into the rooms where I can handle times with other people who usually in the media you’d assume I don’t get along with. Even people that we don’t agree with at all – like on anything,” he said, chopping the air in parallel to his desktop. “I still want to dialogue and be reasonable and level-headed, and I might have an hour-long meeting and think everything you’re saying is crap, but we have an adult conversation and then after the meeting we’ll talk about books,” he said, laughing.
That willingness to engage with others who may fundamentally disagree on some issues is rooted in Haywood’s desire to do what he was elected to do: represent his district.
And that service to his constituents comes with flair. Early into his term he started referring to his Milwaukee district as the “Sensational 16th” – using the phrase early and often in his various social media accounts. The origin of the phrase is interesting, as it’s rooted in the differing elements of the district itself. On one end is a booming downtown district teeming with new development, while the other end includes some of Milwaukee’s highest poverty and crime rates. Those differences within the district, Haywood says, are a major part of what makes the 16th sensational.
“I think my district is full of good and bad, some pretty and some not so pretty,” Haywood said, continuing the explanation. “I think it’s the epicenter of Wisconsin, a district with some great things. The Fiserv Forum downtown – that type of development is booming and areas nearby where real estate is high.
“There are also some areas that are more challenging in the district – 53206 with high population rates of black males who look just like me,” Haywood said. “So know that within all that good and all that bad, all that pretty and not so pretty, I believe that’s what makes it sensational. I think that nothing’s perfect, but we can work to get there. I think there are people who are willing to work to get there, people who are willing to commit to get there.” Haywood’s commitment to the district includes issues challenging to many in his district: personal safety, fighting to emerge from poverty and accessing affordable health care.
“Some don’t know how to sign up for health care,” Haywood said describing what he hears from many of his constituents. “The second issue is that if you get health care and don’t know how to use it efficiently. We need education around being proactive instead of reactive. (I tell people) ‘the emergency room is not the doctor – it’s okay to do a routine check-up; when you have insurance, that’s what it’s there for.’” Haywood says that education needs to continue.
Looking back on his first year in office, Haywood has certainly faced challenges, not the least of which is taking online college classes through Cardinal Stritch University on his way to a degree in business administration – all while attending numerous in-district meetings when he’s not fulfilling his duties in Madison. That daunting schedule has led to the realization that while he was probably already ahead of the post-teen maturity curve upon taking office, the job of representing the “Sensational 16th” has honed that maturity even sharper.
“I think that the job keeps you on your toes,” Haywood said. “I think I’ve grown as a person, definitely. I know that for a fact . . . I’m a completely different person.
“I’ve matured, you know. When I ran, I thought I knew everything – I was like, ‘I’m 18 and I know everything – there’s nothing I don’t know.’ But now, as a seasoned 20-year-old” he said with a laugh, “I definitely think I know a whole lot more. I’ve grown for the better and when I weigh the pros and cons how this last year went there are definitely way more pros than cons.
“I do enjoy what I do. Sacrificing the normal, stereotypical 20-year-old lifestyle was definitely worth it. I get to live out my dream and get to help people make their lives better. If I could do it all over again, I’d do it again.”
Then he paused, flashed his easy smile, and sat back for one more piece of self-deprecating perspective:
“I’d probably be better at it.”
The WHA Legislator Profile is an occasional series by Valued Voice editor Mark Grapentine.

This story originally appeared in the February 06, 2020 edition of WHA Newsletter