Chess.com Expands into Poker with New Gambit Site, More Games Planned

Chess.com, a platform long synonymous with online chess, is now broadening its horizons beyond the 64 squares. The company quietly introduced its first new venture, Gambit, a free online poker website, in beta in May 2026. This expansion marks a significant move for the nearly 20-year-old company, which is now gearing up to host its inaugural livestreamed poker event and collaborate with popular content creators, signaling a broader strategy to enter more classic game territories.

Albert Cheng, Chess.com's chief growth officer, explained that poker was the logical first step due to its inherent learning and social dynamics, mirroring the appeal of chess. He emphasized that Gambit is designed to be a space for learning, explicitly stating there will be no real-money gambling. "Real money is the problem we built Gambit to get away from," Cheng told The Verge. "The whole industry makes money when beginners lose. We’d rather build a place where people can actually learn."

The user interface of Gambit closely resembles that of Chess.com, featuring a familiar design aesthetic and similar game modes. Players can engage in bot matches, challenge friends, participate in tournaments, utilize a review mode for post-game analysis, and access dedicated learning sections. Even recognizable bot characters from Chess.com, including the lowest-level bot "Martin," have made their way to Gambit, each with corresponding skill levels.

Chess.com has also developed a proprietary Elo-style rating system for Gambit, designed to be a primary motivator for player improvement. Cheng highlighted its importance in maintaining player engagement without the financial risks of gambling. "You’re not gambling your own hard-earned money necessarily, so the stakes are lower from that standpoint, but you need something to counterbalance it that you care about, and that keeps the ecosystem in play, and keeps the poker that’s on Gambit reasonably high-quality," he explained.

Strategic Expansion Fueled by AI

This sophisticated rating system underpins Gambit's subscription model for premium learning features, a strategy mirroring Chess.com's established business model. "Our primary business model of Chess.com is a subscription, but most people play Chess.com for free," Cheng noted. "They subscribe to get unlimited access to review their games and to get unlimited puzzles, lessons, et cetera." A robust rating system provides players with a tangible measure of progress, potentially encouraging them to invest in premium features. This same rating system framework is central to Chess.com's future plans, which include expanding into other classic games such as go, backgammon, and mahjong. While Cheng did not provide specific launch dates for these new ventures, he confirmed that "development is moving quite rapidly," employing the successful playbook used for Gambit.

Artificial intelligence has played a pivotal role in enabling Chess.com's expansion after nearly two decades. Cheng indicated that AI significantly accelerated the development of Gambit, assisting with coding tasks and allowing a small team to transition the platform from prototype to launch within a year. "I think the biggest advantage that it’s provided is essentially being able to read our existing codebase and our design system and apply consistent patterns to how we develop Chess.com over to a different platform and do so quickly," Cheng stated. However, he also acknowledged AI's limitations, particularly in areas like brand identity and feature design, suggesting that the optimal approach involves a blend of AI assistance and human expertise. "I think that’s the best ultimate use of AI is that ultimately it’s going to be a blend, right?" he mused. "Just because code is easier to write doesn’t mean that you just let it run on its own, but it certainly is a superpower in getting things off the ground."

Cheng clarified that the current live version of Gambit contains minimal to no AI-generated assets, though such assets were used in earlier development stages. He believes that without AI's contribution, launching a new site would have demanded a larger team or posed a greater disruption to the company's growth trajectory. The ability for a "small, scrappy" team to rapidly develop new platforms has now opened the door for Chess.com to explore additional game genres, commencing with poker. As Chess.com strategizes its next moves, it is focusing on games that possess both "classic durability plus the community around it," akin to chess. With Gambit now live, Cheng is prioritizing the cultivation of its community and social aspects, mirroring Chess.com's successful approach and actively engaging content creators. The platform will host its first Gambit Cup livestream on August 31, 2026, at 12 PM ET / 9 AM PT, broadcast on Twitch and YouTube, featuring Chess.com co-founder Danny Rensch and chess content creator Alexandra Botez.