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Alex Bowman entered NASCAR's weekend in the Windy City with a road course resume you'd easily overlook. In 32 career Cup Series starts on this track type, he'd led just five laps; in the rain-filled edition of Chicago's race last season, he crashed out and finished 37th.

This year? He left the streets by Lake Michigan an unlikely race winner.

Bowman and crew chief Blake Harris took advantage of another dose of wet weather, one that ultimately turned Sunday's second edition of this street race into a timed event. Staying out during a stage break, he jumped toward the front, gambling track position would run out the clock against faster cars who switched to faster, slick tires on drying asphalt.

"As those cautions kept coming," Harris explained. "We got to that stage [break] and it was like, wait a second, we have like eight, ten laps here to go. . Like there's a chance [to win if we stay out]. If there's a caution or two, there's a chance."

That's exactly what happened, one late yellow draining the time Bowman needed after passing road course ringer Joey Hand to take the lead. Just enough slower cars got in the way of fast-closing Tyler Reddick, who cleared traffic and had to get overaggressive to have any chance. When Reddick hit the wall on the final lap giving chase, it was the extra bit Bowman needed to trudge toward an upset win as darkness fell.

Consider the circumstances for Bowman heading in, boasting longshot odds of 60/1 according to Sportsline. He hadn't won since Las Vegas in March 2022, a span of nearly 2 ½ years. Since then, he's suffered through two serious injuries (concussion, back) and entered this weekend leading just six laps in all of 2024.

On Sunday, he was out front for the final eight, raising eyebrows and popping a balloon of speculation that swells whenever you underperform at Hendrick Motorsports, the most successful team in NASCAR history.

"At some point," HMS Vice Chairman Jeff Gordon admitted, "You've got to win. Not just because you're at Hendrick Motorsports, it's because it's really hard to get the team where they need to be to compete at the highest level on a regular basis."

Bowman heard the noise, only growing louder after the demise of Stewart-Haas Racing sparked a stronger burst of Silly Season activity than usual. A contract extension through 2026 failed to quiet doubters as they watched Bowman's three teammates all secure playoff-clinching wins with ease.

"As a human being," Bowman said, "I'm just a dude trying to do my job the best I possibly can, and I see everything that gets said about me. So to be able to overcome what I've gone through and to end up back here, it feels really good."

With the win, Bowman arguably becomes the third driver to secure a long-term future that hung in the balance. Daniel Suarez bought time at Trackhouse with his February win at Atlanta Motor Speedway, ensuring he'll be one of three drivers kept on for 2025. Austin Cindric, despite a contract similar to Bowman, appeared destined for the exits at Team Penske before teammate Ryan Blaney ran out of gas at Gateway, handing him the win.

It's created a trio of wild cards with monkeys off their backs and nothing to lose entering the playoffs. And in a year that started with a select group of drivers ahead of the pack, it's nice to see a little bit of unpredictability into this year's postseason field.

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Green: Joey Hand. Joey who? The sports car veteran had an uneventful career as a NASCAR road course ringer before nearly pulling off the type of upset Shane van Gisbergen did last year. In the end, Hand couldn't keep up with Bowman on similar strategy, but a fourth-place finish is nothing to sneeze at for a driver in a part-time third car for RFK Racing.

Yellow: Tyler Reddick. Second, indeed, is the first loser for a driver who's given up a shot at victories so close he could taste them for two straight weeks. Top-five finishes are meaningless for someone who long ago clinched a spot in the playoffs; instead, he missed out on precious bonus points. "We were catching Alex by a large margin there, and … I clearly just screwed up," Reddick said. "Trying to stay in the dry groove and… I cut the wheel a little too hard."

Red: Christopher Bell. How many times this year has Bell been the fastest car only to find himself wrecked out of the race? This time, it was a tangle with teammate Martin Truex Jr. that left the No. 20 Toyota sitting out after leading 14 laps. Bell's now crashed out five times this season, tying a career high with 16 races still to go.

Speeding Ticket: Shane van Gisbergen and Kyle Larson. SVG entered Sunday the overwhelming pre-race favorite to go back-to-back on the street course. Larson, the pole sitter, was his biggest rival, the two staging a remarkable duel in Saturday's NASCAR Xfinity Series race before SVG came out on top.

Who would have guessed they'd end Sunday's race as the first two cars who failed to finish?

SVG went first, an innocent victim when Chase Briscoe lost control in front of his No. 16 Chevrolet.

Larson joined SVG inside the garage moments later, locking up the brakes on a wet track and slamming head-on into Turn 6 in the day's hardest wreck.

Oops!

Bowman's win was slightly overshadowed by early contact with Bubba Wallace that ruined a top-10 run for a No. 23 Toyota team fighting for their playoff lives.

Wallace still staged a valiant comeback, climbing to 13th by the checkered flag but was fuming in the cockpit most of the day with a driver he's got a history with. Wallace took time to express displeasure to Bowman after the race, hitting the No. 48 Chevrolet with Bowman's window net down in a move that will likely produce at minimum a hefty NASCAR fine.

Count Bowman among those who doesn't believe Wallace should be seriously penalized. The first thing he did upon exiting his race car was apologize before celebrating the victory.

"Just messed up," Bowman explained. "Trying to get my windshield wiper on, missed a corner and ruined their day. I hate that. I'm still embarrassed about it."