Denny Hamlin’s chaotic weekend in Chicago became more than just a race; it was a collision of branding, bad luck, and unwavering ambition. Hamlin began the 2025 season with uncertainty, a new crew chief and a lack of sponsors, but he bounced back with intent, including a win at Martinsville in March that fulfilled a decade-long desire. He later stood atop the podium at Darlington and Michigan, reinforcing his status as a championship threat. However, mechanical woes, including DNFs at Texas and Kansas, emerged as recurring setbacks, threatening to derail what had been a highly promising early season.

Coming back to this weekend, that marks the third edition of NASCAR’s Grant Park 165 on Chicago’s temporary 2.2-mile street circuit, anticipation is high as drivers tackle the notoriously rough surface shaped by Midwest weather and city traffic. For the 23XI Racing team, this is their home turf. Michael Jordan won six NBA titles with the Chicago Bulls, plus their sponsors like McDonald’s, have their headquarters in the Windy City. So as far as brand activation goes, they wen’t All-In.

In a bold marketing pivot, a record-setting collaboration with a #110 billion-valued partner, Jordan, backed Hamlin’s weekend in Chicago, elevating the event’s stage before a huge NASCAR audience. In the video shared by Hamlin on Instagram, captioned, “@jumpman23 x Chi-Town 🔥,” his family can be seen enjoying the show as the drifting car catches fire, as Hamlin explains, “It looks familiar. Hood up, car’s on fire, blowing up,” as he crouches low to escape the searing heat, and his daughters, Taylor and Molly, stand frozen nearby, clutching their chests in fear. The sheer novelty of asphalt weaving between Grant Park’s green expanses and Lake Michigan’s skyline added gravitas to this high-stakes commercial pairing and immediately stoked social media.

 

What happened earlier in the day shocked fans even more as disaster struck before Hamlin even reached qualifying. During the first practice on Saturday, his #11 Toyota’s engine blew the bottom out just past Turn 4. He later vented frustration in the paddock, telling TNT Sports, “I hadn’t even hit the gas yet. Came off Turn 4, just started accelerating and blew the whole bottom out,” and lamenting the setback with team leadership. The outcome was grim, with no qualifying run and a start at the rear of the field, making it a major handicap on the narrow street layout.

Chicago hasn’t been kind to Hamlin in the past street-race editions either. In the inaugural 2023 Cup Series event, he secured pole only to crash on Lap 2, though he rebounded to finish 11th. The 2024 iteration was even more unforgiving, with setup struggles and perhaps lingering emotional hang-ups seeing him slip to 30th. Without any practice on Saturday, Hamlin faced echoes of these past struggles, yet again needing to navigate a city circuit that rewards and punishes missteps. But fans have been weaving all of the incidents together to put out hilarious comments under Hamlin’s post, just as they wait for the action to unfold at the Chicago track for one last time.

Social media reacts to Hamlin’s wild weekend

“He said “looks familiar” RIP Denny’s car in practice,” one fan commented, taking into account the previous incident. The scene looked familiar to Hamlin because earlier that day, his own car sputtered to life when he immediately blew its bottom-end engine past Turn 4, dumping oil, smoking heavily, and spiraling off the course before he could even set a pace lap. As the engine exploded minutes into the session, Hamlin could only watch in disbelief. Later in the pits, he erupted in a heated debrief with both team owner Joe Gibbs and competition director Chris Gabehart. The déjà vu in his tone underscored the recurring struggle Chicago’s technical circuit has posed for Hamlin, turning what was meant to be a sharp lead-in into a familiar comedy of errors.

Another praised the promotional event, saying, “Jordans Promotion in Chicago, Can’t get any better than that.”  This weekend’s race at Chicago will see the #45 Toyota from 23XI Racing turning heads with a bold Jordan Brand paint scheme, featuring the iconic “Shattered Backboard” design and Jumpman logo prominently displayed on the hood, an homage that driver Tyler Reddick unveiled via Instagram with the teaser “Shattered backboards and brackets.” The scheme nods to the famed 1985 Jordan poster, the very image that inspired today’s Jumpman logo, which makes this promotional event even more memorable.

“That for sure Isn’t Reddick doing drag,” another fan joked, hinting at the collaboration between Reddick and Jordan, which is true as his 2025 stats tell a different story. Through 17 Cup races, Tyler Reddick has secured 1 pole, not flashy burnouts, and delivered zero wins so far, although he has recorded four Top-5s, and six Top-10s, ranking 13th in points with 533. Rather than theatrics, Reddick’s strength has been consistency, including a thrilling stage-win photo finish at EchoPark Speedway, edging out Chase Elliott by 0.001 seconds. Perhaps, he can give this fan a rebuttal with a victory lane visit soon.

Some others did not understand the hype behind the promotional event, as one fan wrote,

“Why there’s a crowd just to see some random car do burnouts and donuts? Chicago is weird.” Burnouts and donuts at the NASCAR Chicago race aren’t random stunts; they are ritual celebrations rooted in motorsport history. But more importantly, this was an activation event that saw NASCAR stars like Hamlin and Reddick represent Michael Jordan’s brand.

One fan had a deep-rooted connection with such shows of drift and speed, as they commented,

“You should go to Formula Drift in Seattle!” Formula Drift’s Seattle round at Evergreen Speedway consistently draws massive and passionate crowds, often selling out its 15,000-seat grandstands with over 13,000 spectators in 2024, making it one of the loudest and most fan-friendly stops on the tour. Attendees rave about being able to get up close to the cars and mechanics, with many calling it electric and unreal, even during less intense moments, making the event worthwhile.

For many, the thrill isn’t just about the car’s identity but the sound, smoke, and spectacle that turned the streets into a live arena. Kids on shoulders, seasoned fans comparing it to Daytona, and live concerts, all added to the electricity in the air. What looked like chaos to some was tradition in motion to others. In that moment, Chicago wasn’t just watching motorsport; it was feeling it.