From the Ballfield to the Ballroom: How Chris Maliszewski Turned Energy, Trauma, and Purpose into a Life of Impact

Chris Maliszewski, raising lots of money at an event!

If you've ever watched someone lead a room — really lead it — you can usually trace it back to the first place they learned how. For Chris Maliszewski, that place wasn't a boardroom. It was a baseball field.

Before the galas, live auctions, and microphones, Chris spent a decade coaching Division I baseball at Iowa (the same field where he played). Coaching at that level is a masterclass in pressure, preparation, and performance. You're building relationships. You're motivating young athletes who think they already know the answer. You're running a tight schedule whether you feel ready or not. And you're constantly figuring out how to get people to buy in.

Here's the part that matters: Chris wasn't just coaching baseball. He was coaching belief. It turns out, belief is the same thing you need when you're asking someone to open their heart and their wallet for something that matters.

The fundraising muscle was there early… even if the job title wasn't

Chris will tell you he never technically "worked for a nonprofit." But fundraising has been part of his professional DNA for a long time.

Even as a coach, he was managing booster relationships and raising money for his teams — travel costs, equipment, facilities, all of it. At places like Iowa, there was more support. At Valparaiso, less. Either way, the lesson was the same: if you want something better for your people, you have to go out and build the support for it.

That mindset followed him into his next chapter at the Park District of Highland Park. What he saw there was something a lot of us have seen in organizations: a good program, a meaningful mission, and little fundraising structure around it. The Park District had the Smile Grant-in-Aid program, helping families afford recreation — sports, camps, and activities, the stuff that builds confidence and community. At the time, there wasn't a real fundraising engine behind it.

So Chris did what a coach does. He built one.

The Champions Gala

In 2016, Chris launched the Champions Gala, a sports-themed fundraising event designed to raise money for the Smile Grant-in-Aid program. Year one: about 115 people, $15K–$18K raised, and a keynote speaker most people would be thrilled to meet on a random Tuesday — Fergie Jenkins.

While some people might balk at those numbers, Chris wasn't concerned. He already understood: fundraising takes time, and this was not a one-time event. He was building a repeatable system. Chris hustled, and each year the event and the speakers grew.

2017 brought Denis Savard. More people. More dollars. More buzz. 2018 brought Ozzie Guillén, a bigger room, bigger energy, and suddenly fundraising wasn't just a program — it was becoming a community tradition. By 2019, the event sold out with Mike Ditka headlining, raising over $50,000. Then COVID hit, events paused, and the world changed.

Here's what didn't pause: the impact of what Chris built. The Champions Gala didn't just raise money. It created momentum, so much so that it helped catalyze the creation of the Parks Foundation of Highland Park, a structure that could grow beyond one event and start thinking long-term. That's not easy. A lot of organizations talk about starting a foundation. Chris helped make it real. And along the way, he wasn't just bringing in names, he was creating experiences donors would never forget.

The sports icons weren't the headline. The generosity was.

Chris Chelios (left, former Blackhawk star) standing next to Chris Maliszewski and others.

One of the things Chris said that stuck with me: working with these legends was… easy. You'd assume icons like Ditka or Chelios would be complicated. Or that Ozzie would be a headache. Nope. They showed up. They cared. They stayed late. They signed autographs. They talked to people like human beings. And when Chris talks about them, what comes through isn't celebrity. It's heart.

My favorite story

At the Ozzie Guillén gala, they auctioned off a package where Ozzie would golf with the winner at Sunset Golf Club in Highland Park. It somehow sold twice. Chris recalled with excitement, "The second winner basically said, 'We hate golf. Can we just hang out with Ozzie?'" Ozzie didn't even blink.

The group came up with a fun idea; why not attend a Cubs rooftop party with the baseball legend. Ozzie hung out with strangers on a rooftop, and it created a legendary night for everyone. That's the kind of thing people tell their friends about for the rest of their lives.

Same with Chris Chelios. They auctioned off a yacht party with him on Lake Michigan. Chris explained, "This was not a meet-and-greet. It was an experience. Something unforgettable."

Chris was ahead of his time with experiential fundraising.

And then July 4th happened

If you live in Highland Park, you don't need a recap of July 4, 2022. Like me, you remember it in your body.

Chris wasn't just there that day. He was a co-chair and organizer of the parade — the person directing traffic at the front of the route, coordinating the moving pieces, working the operation he knew "backwards and forwards." And at 10:14 a.m., chaos erupted.

Chris stayed in Highland Park until around 6 p.m., working with law enforcement to help locate and evacuate people. At one point, he went down to Rosewood Beach with a police escort to evacuate people who didn't realize the severity of what was happening.

When Chris tells this story, it's not dramatic. It's factual. That's how you know it's real trauma — because trauma doesn't always sound emotional in the moment. When the adrenaline fades, it shows up in other ways.

For Chris, one of those moments came during a lockdown in 2023, when he experienced his first panic attack at work. Chris said, "That was the turning point. The moment my body said: you can't just push through this. I knew I had to take healing seriously." He took a leave of absence and started a journey toward mental health. Through therapy, exercise, nature, and psychiatry, Chris began to heal. As Chris reflected, "Time helps, but you're not the same person afterward."

Hail Hail: the pivot that became a calling

Chris Maliszewski at a charity event

Somewhere in the middle of rebuilding, another door opened. In 2023, at the Champions Gala (which by then had grown to about 250+ attendees and nearly $100K raised), Chris hired a professional auctioneer: Chris Hensley, of Bid Raise Bid.

Backstage, after Chris Maliszewski had given remarks, Chris Chelios looked at him and said, "You're really good on the mic." Then Hensley said the sentence that changed everything: "You could do this."

At the time, Chris brushed it off. He had a job. A career. A lane. But when Chris was no longer at the Park District, he knew one thing: he wanted to build something of his own. So he called Hensley back.

Hensley didn't just give him a tip or a pep talk — he mentored him, helped him get licensed, opened doors, and became the kind of professional ally most people hope they'll find once in their career. Within three months of becoming an auctioneer, Chris was being flown to major events, including Times Square. That's not luck. That's talent + preparation + presence.

Chris leans hard into that preparation piece. He researches every organization. He learns the mission. Meets the players. Understands the flow of the night. Because to him, being an auctioneer isn't just reading numbers fast. It's being invested enough that the room can feel it. He put it simply: "There are two things I can control — preparation and energy." Everything else? Weather. Travel. Chaos. The schedule. The curveballs? That's out of his control and just part of the game.

The Appeal Podcast: relationship-building as a strategy

To stand out in a crowded market, Chris launched a podcast called The Appeal — a platform where he interviews nonprofit leaders and uplifts their work. It's smart for marketing, but it's more than that. It's how he builds relationships before he ever takes the stage. Chris makes nonprofit professionals feel seen in a world that often overlooks them unless there's a gala involved. That's Chris in a nutshell: bring people in, make it meaningful, and create momentum.

Walking Tall: turning trauma into advocacy

Chris could've stopped there. New business. New identity. New lane. But three days after the Highland Park shooting, Chris got a text from Todd Blyleven — son of Hall of Fame pitcher Bert Blyleven — also a survivor of the Las Vegas mass shooting in 2017. That conversation became a relationship… which became a podcast… which became a nonprofit.

Chris co-founded the Walking Tall Movement, focused on mental health advocacy and support for trauma survivors. They eventually added a psychologist and received their 501(c)(3) status at the end of last year. Since then, they've been building workshops, on-site support for organizations, keynote speaking, and storytelling that helps people feel less alone.

Chris recently did work with Kentucky State University after a campus shooting and spoke at the Illinois Jaycees conference. They're volunteer-run and building a fundraising base through efforts like a March Madness bracket challenge — not just to raise money, but to build community and a database for the future. It's early. It's scrappy. It's real. And it exists because Chris refused to let tragedy be the end of the story.

The through-line: coaching never stops

Chris is still coaching. Just not in cleats. He coaches rooms full of donors into courage. He coaches nonprofits into better fundraising. He coaches trauma survivors with permission to talk about what happened.

Most importantly, he coaches himself into balance — protecting his energy, choosing downtime, building a life that is sustainable, not just impressive.

He's also a dad. A human being. Someone who openly admits the stimulation of constant events can be a lot. Chris has learned how to rest on purpose so he can show up at full strength when it matters.

If you're reading this and you run nonprofit events, I'll leave you with one takeaway Chris said that stuck with me: "A professional auctioneer isn't a luxury. It's a strategy."

The right auctioneer prepares, connects, lifts the room, and helps people give in a way that feels energizing — not transactional. And Chris? Chris brings energy and heart.

To learn more about Chris, visit: https://www.hailhailauctions.com/

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I help nonprofits raise more money through education, coaching, and strategic planning. I also lead high-impact professional development, coaching programs, and retreats for companies of all sizes. If you’re ready to strengthen your fundraising strategy, turn board members into advocates, or build a comprehensive legacy giving program, let’s talk.