NASCAR's Shane van Gisbergen is hoping for another successful weekend in downtown Chicago

CHICAGO (AP) — The first time Shane van Gisbergen raced in Chicago, he was largely unknown in NASCAR. The second time, he was one of the favorites on the downtown street course.

The third time is a different situation for van Gisbergen once again. This time, he has a second Cup Series victory in his back pocket — providing some flexibility for the 36-year-old New Zealand native as he prepares for the playoffs.

“We’re in a nice position now having won a race,” van Gisbergen said Friday. “And it may change our strategy. If we’re in a position to get a playoff point, we’ll probably try and get that, but that’ll put us deep in the field for the next stage. So yeah, there’s a bit of a toss-up there what we’re going to do, but it’s a nice position to be in.”

Sure is.

Just two years ago, van Gisbergen — a three-time champion in Australia’s Supercars — put on a dazzling show in a rainy first edition of NASCAR's downtown Chicago experiment. Making the most of his extensive street racing experience, he became the first driver to win his Cup Series debut since Johnny Rutherford in the second qualifying race at Daytona in 1963.

He won Chicago's Xfinity Series stop last year and the first stage in the Cup race before he was knocked out by a crash.

“You know, I have great memories here," van Gisbergen said. "This place has changed my life, so I’m going to have special memories of this place forever.”

Van Gisbergen's success in Chicago led to a full-time Cup ride with Trackhouse Racing. But the driver of the No. 88 Chevrolet is learning his way around NASCAR and he got off to a slow start this season.

While oval tracks remain a challenge, he certainly hasn't forgotten his roots on street and road courses. He posted his second Cup win last month at Autódromo Hermanos Rodríguez in Mexico City.

Van Gisbergen is scheduled to compete in both Chicago races this weekend. Next up for NASCAR is another road course at Sonoma Raceway, providing an opportunity to move up from No. 32 in the Cup standings and build up some momentum.

“Road courses are just a bonus for us,” he said. "We know we’re going to be good and we can just focus on trying to get results there.”

Even after two years, the downtown Chicago street course remains a tricky proposition. The 12-turn, 2.2-mile track is narrow and bumpy in spots — to go along with manhole covers, and transitions from concrete to asphalt and back — and there is little room for error in some areas. Rain affected the action in each of the first two weekends, and there could be more showers on Sunday.

Patience is sometimes the best approach, but that only goes so far in NASCAR.

“It’s easy to say that until Shane is out there a second faster than you and you have to go put yourself in some uncomfortable situations,” said Joey Logano, the reigning Cup Series champion.

When it comes to van Gisbergen on road courses, Logano said the rest of the Cup Series is "in a way, playing catch-up.” Van Gisbergen said he feels the same way about ovals.

“These guys have been doing left-handers since they were 10 years old,” van Gisbergen said. "You know, they’re two completely different sports, and although there has been road racing in NASCAR forever, it’s not that much. So yeah, just the experience levels are different in what we do. And I feel like, yes, they’ve definitely gotten a lot better since the first one on this track, for sure.”

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FILE - Shane Van Gisbergen celebrates after winning a NASCAR Cup Series auto race at the Grant Park 220 July 2, 2023, in Chicago. (AP Photo/Morry Gash, File)

WEST PALM BEACH, Fla. (AP) — President Donald Trump on Sunday fired off another warning to the government of Cuba as the close ally of Venezuela braces for potential widespread unrest after Nicolás Maduro was deposed as Venezuela's leader.

Cuba, a major beneficiary of Venezuelan oil, has now been cut off from those shipments as U.S. forces continue to seize tankers in an effort to control the production, refining and global distribution of the country's oil products.

Trump said on social media that Cuba long lived off Venezuelan oil and money and had offered security in return, “BUT NOT ANYMORE!”

“THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA - ZERO!” Trump said in the post as he spent the weekend at his home in southern Florida. “I strongly suggest they make a deal, BEFORE IT IS TOO LATE.” He did not explain what kind of deal.

The Cuban government said 32 of its military personnel were killed during the American operation last weekend that captured Maduro. The personnel from Cuba’s two main security agencies were in Caracas, the Venezuelan capital, as part of an agreement between Cuba and Venezuela.

“Venezuela doesn’t need protection anymore from the thugs and extortionists who held them hostage for so many years,” Trump said Sunday. “Venezuela now has the United States of America, the most powerful military in the World (by far!), to protect them, and protect them we will.”

Trump also responded to another account’s social media post predicting that his secretary of state, Marco Rubio, will be president of Cuba: “Sounds good to me!” Trump said.

Trump and top administration officials have taken an increasingly aggressive tone toward Cuba, which had been kept economically afloat by Venezuela. Long before Maduro's capture, severe blackouts were sidelining life in Cuba, where people endured long lines at gas stations and supermarkets amid the island’s worst economic crisis in decades.

Trump has said previously that the Cuban economy, battered by years of a U.S. embargo, would slide further with the ouster of Maduro.

“It’s going down,” Trump said of Cuba. “It’s going down for the count.”

A person watches the oil tanker Ocean Mariner, Monrovia, arrive to the bay in Havana, Cuba, Friday, Jan. 9, 2026. (AP Photo/Ramon Espinosa)

President Donald Trump attends a meeting with oil executives in the East Room of the White House, Friday, Jan. 9, 2026, in Washington. (AP Photo/Alex Brandon)