Can chess become the new poker?

He used to fall asleep dreaming about his moves.

You’d expect as much from an All-Pro NBA point guard whose mind was known to move as swiftly as his feet on a fast break, enabling him to distribute the ball with the precision and explosiveness of a laser-guided missile.

But it wasn’t always his play on the court that invaded Derrick Rose’s slumber each night.

He had a new obsession: chess.

“When I was playing, it used to irritate me,” Rose grins during a recent Zoom call, reflecting on his love for chess during his NBA career. “I used to get up like, ‘Man, this can’t be my No. 1.’ ”

Rose, 36, retired from the league in September after an accolade-laden 16-year career in which the three-time All-Star and 2009 Rookie of the Year became the youngest player ever to win MVP, at 22 years old in 2011.

Now, chess can be his No. 1.

The result?

Chesstival, a new pro-am, freestyle chess event that Rose helped conceptualize. It premieres at Wynn Las Vegas on Sunday and will be held in conjunction with the U.S. debut of the Freestyle Chess Grand Slam Tour at Wynn from Wednesday to July 20.

Chesstival features two competitions in one day: First, current and former NBA players like Marcus Smart, Drew Gooden, Tony Snell and others team up with a chess master to challenge another duo in a “Head & Hand” format, in which one player names a chess piece and the other player decides where to move it.

Next, the basketball vets go head-to-head in a Blitz chess tournament.

Both competitions feature a $25,000 prize pool with proceeds going to the winners’ charities of choice.

Chesstival sets the stage for the Freestyle Chess Grand Slam, a new global league founded by five-time world chess champion Magnus Carlsen and German entrepreneur Jan Henric Buettner. (Rose is also an investor.)

The Vegas tour stop, the first with a live audience, will feature 16 of the world’s best chess masters — including Carlsen — competing for $750,000 in prize money.

It’s all part of a larger attempt to elevate chess into a more mainstream attraction, similar to how esports and poker have been vaulted into the public consciousness in recent decades.

Taken together, the two competitions mark the biggest chess gathering in Vegas since the FIDE World Championship was held at Caesars Palace in 1999.

“It’s not often that you have a chess event of this magnitude,” notes Angelo Agbayani, president of the UNLV Chess Club. “Of course, there’s big chess events like the National Open and the North American Open, but those are national tournaments. It’s actually been awhile since Vegas has had an event like this.”

Defining the terms

OK, so what exactly is freestyle chess?

Developed by chess titan Bobby Fischer in 1996 — and also known as Fischer Random Chess or Chess960 — it’s a twist on the game that emphasizes spontaneity by randomly placing the pieces on the first and eighth ranks.

The result is 960 possible starting positions, rendering it impossible to plan initial moves in advance.

“It’s like another variant of chess,” Agbayani explains. “For the locals who maybe play poker, they could think of it like the difference between Omaha versus Texas Hold’em. It’s the same game, except the back row of pieces is shuffled, so you will never start the game the same. It will always be different.”

Basically, freestyle chess demands that players think on their feet — and think fast — kind of like an NBA point guard searching for an assist with the shot clock expiring.

For Rose, the skills that made him a basketball star directly inform his prowess at chess — and vice versa.

“I feel like it’s just staying steps ahead and critically thinking while you’re getting pressure,” the Illinois native says, citing his own background as an example. “Living in Chicago, I was thrown into the game of basketball at an early age. Being able to play against all the guys that was older than me, I had to play with a lot of pressure on me. So I feel like that’s the parallels of the pressure part and realizing that you can always get better.

“I learned how to move the pieces early on in my NBA career, but I never took it further than that,” he continues of his gradual immersion into chess. “It went from that to me playing against my friends, to them getting obsessed with it, to us playing all day throughout the summers, betting pushups for games.”

Rose began taking those games more and more seriously — maybe a bit too seriously, upon occasion.

“Chess is very draining,” he says. “When you lose, it’s different. In basketball, I take it kind of hard. In chess, I take it really hard. It makes me want to fight right away, whenever I lose.”

Notorious for playing at a breakneck pace on the basketball court, Rose was naturally drawn to the fast action of freestyle chess.

“With less ties at the end, draws at the end, it’s perfect for Blitz (chess), short games,” he says. “It’s like a shootout in basketball: You get in, you get out, you see whoever the champion is.”

‘The greatest sleeping pill’

He couldn’t understand why anyone would want to watch something so, well, boring.

A few years back, German entrepreneur Buettner, who ran AOL Germany before founding his own successful venture capital business in California, was approached about hosting a chess tournament at his luxury resort Schloss Weissenhaus, which he opened in his home country a decade ago.

“I’m like, ‘OK, what’s a chess tournament? I have no idea,’” Buettner recalls during a phone interview from Hamburg, Germany. “So I looked and I watched, and I found the greatest sleeping pill of all time: watching two people play chess.”

But Buettner notes that he likes a good challenge, and here was a big one: make chess fun to watch.

For inspiration, he turned to the diametric opposite of observing two intellectual types match wits at a snail’s pace: Formula One racing.

Having traveled the F1 circuit as a fan, including last year’s Vegas race, Buettner sought to infuse the pomp, showmanship and storylines of that sport into the staid, stuffy world of chess.

“It’s like, ‘Wow, look at how they treat the Formula One drivers,’” he says. “They are superstars that fly around in jets, and the chess players are sitting in their training suit or whatever, in their street wear in some gyms.

“What is more boring than watching two people play chess?” he continues. “It’s basically like having fast cars driving by with no context, right? It’s more about the personality stories and the colors and the excitement and the gaming around it. So I’m like, ‘Challenge accepted: Let’s do the best chess tournament the world has ever seen in my Weissenhaus. What do I need for the best chess tournament of all time? I need the greatest chess player of all time.’”

Enter Magnus Carlsen. He met Buettner at a chess event in Qatar and hipped him to the idea of a freestyle chess tournament with some of the world’s best players.

“I got it, you know — it makes the boring game of chess more interesting,” Buettner says. “Like in basketball, where they introduced the 3-point line. It makes a totally different game, right?”

‘All hell broke loose’

The inaugural Freestyle Chess G.O.A.T. Tournament debuted at Buettner’s resort in February 2024.

It lost money, but gained fans.

“We just did it because we had this idea and no business plan behind it,” Buettner says. “In the end, it cost me $2 million to do it. But it was exciting. It was great.

“During the tournament — in the positive sense — all hell broke loose,” he continues. “Everybody calls me, ‘That’s the greatest thing.’ We had, like, a billion impressions. Everybody’s like, ‘I think we have to do something about it.’”

And so the Freestyle Chess Grand Slam Tour was born, with five cities booked for 2025, Vegas being the fourth stop after two in Germany and one in Paris.

Rose came aboard as an investor, bringing Chesstival with him.

“It’s a real partnership,” he says. “We could give these people in the chess world an experience to see something that’s new — not trying to disrespect the traditional chess or chess players, but just trying to add to the game and bring people to the game.”

Chesstival was supposed to launch here last summer, but Rose — who had yet to officially retire from the NBA — acknowledges that he didn’t commit enough energy to the event at the time.

“I felt like I failed doing my part, which is to reach out to the players, and it fell apart,” he says. “So this time around, because I’m not playing (basketball), I’m able to be more hands on, and we got it done.”

For all parties involved, the key to growing chess is making the game an entertainment event, a social gathering, a happening, with more widespread appeal — even for those who couldn’t possibly distinguish a Sicilian defense from its French counterpart.

“Who is watching chess tournaments? Chess players, right?” Buettner asks. “So, who is watching Formula One? Racers only? No, everybody watches.

“Even if you go to Formula One races, most of the people are not even interested in the race,” he continues. “They are mingling with each other. They do business deals. They have good food. ‘Oh, the race’s going on? Really? Who’s winning?’ This kind of thing. We are following the same model.”

That means an emphasis on audience engagement, highlighting the players’ personalities and bringing fans behind the scenes.

“We put the players in velvet jackets of different colors; every player has this individual color we recognize by the fans,” Buettner says. “We also have some other interesting stuff, like a pulse monitor, so that the spectators can see how the pulses are going when they do the moves, and a confession booth, when they talk to the audience about their moves and so on.”

For Rose, who’s doing his part to bring fresh eyes to the game by recruiting NBA players to play publicly, teaming up with Buettner and Carlsen is the rare chess move that doesn’t require a whole lot of deep thinking — or loss of sleep.

“I partnered with them because I saw their idea, I saw their dream,” he says. “It’s me loving the game. It’s me being obsessed with the game.

“And that’s what the game does,” he adds. “It pulls you in.”