
Dan O’Conor could not have imagined the impact of the spontaneous leap he took into Lake Michigan on June 13, 2020.
He just knew he was tired, hungover and frustrated by the pandemic. At his wife’s urging, he took a walk to clear his head and, as he passed a wall near Montrose Harbor, he hopped in.
He liked the way that clear, cold water made him feel. So, the next day he did it again.
“I think I found something that makes me feel better and, from a mental health standpoint, I think we all need to find something that makes us feel better and, even if it’s two minutes of zen down at the lakefront, you need to chase that,” he said.
As he started recording his jumps and posting them to his social media accounts, he became the ambassador of good cheer and live music known widely known as the Great Lake Jumper.
Egged on by people who told him he’d never be able to do it, O’Conor set a goal of jumping every day for a year. As his profile increased, he used it to raise funds for his favorite charity, CIVL, a group that advocates on behalf of Chicago’s independent performance venues.
Eventually, he started inviting local musicians to perform as he jumped.
“When I started inviting musicians, it was because they were around (due to the pandemic) and they were looking for any creative outlet,” he said. “The clubs were closed and even to come out and play one or two songs, it meant a lot to them. I heard from a lot of artists that said thanks.”
He took his coldest jump on a day the windchill hit -19.
“I felt as bad for the musician that day as I did for myself,” he said. “They’re standing on a snowbank. Once you get in the water, it feels pretty good. It’s shocking at first but then there’s an endorphin rush. It’s the wind that gets you.”
Summer weather in Chicago also challenged the streak.
“It was August, a couple of months in, and my son and I rode bikes down to the lake. We saw helicopters and police cars everywhere. When we pulled up on our bikes, there were probably five police cars on the grass and a low flying helicopter. It looked like a recovery mission not a rescue mission. It was rough. I thought we weren’t going to be able to jump. Then, out of the corner of my eye, I see this guy who’s about 70 or 75 and he’s walking to the water and he’s going in and I thought, ‘Well, if he’s going in I’m going in.’”
Until the snow made it impossible, O’Conor rode his bike the three miles from his house to the lakefront. Once he had to start taking his car, he encountered some other logistical challenges familiar to Chicagoans – how to avoid a parking ticket.
“I still have the note in my car. It says ‘Jumping in lake. Back in five minutes.’”
Toward the end of his year-long streak, he started to feel extra pressure to finish it.
“In that first year I became obsessed,” he said.”I felt like I’m inviting people to a 365-day party and I didn’t want to let them down. I started to be really careful because I didn’t want to break a leg or do anything that might prevent me from going in.”
He crossed that finish line with a big party, took the next day off, and then set a new goal to jump in all five Great Lakes. He swung through Green Bay on his way back from completing that quest, and he jumped in from Louie’s Lagoon.
Next up is a swing through New England with a goal of hitting all five states in a single day.
“I’m just mapping it out now. I need to find a place to jump in Southeast Vermont.”
And then?
“Well, Minnesota has 10,000 lakes,” he said. “I don’t want to say that would be impossible, but it would be monumental.”
I think he’s kidding, but, who knows? I recommend you follow him to find out. I guarantee he’ll make you smile.

Dan posts videos of his jumps on his Twitter and Instagram accounts. I like this freeze frame because it shows the skyline, the musician and exactly how enthusiastic those jumps are. He doesn’t mess around.







