Prediction market participants on the federally authorized platform Kalshi indicate low confidence that the United States will acquire new territory, despite President Donald Trump's public comments regarding Greenland, Kharg Island, and Canada. Data from the platform reveals that over $770,000 has been bet on the contract "Will the US acquire any new territory?" with the highest probability peaking at 22% for an acquisition occurring before Jan 21, 2029, the scheduled end of Trump's term.

Trump's Territorial Interests

Trump has repeatedly emphasized the strategic importance of Greenland, an autonomous territory of the Kingdom of Denmark. During a NATO summit in Ankara on July 8, he stated, "We took Greenland and then, stupidly, we gave it back." He argued that the US needs the island for the protection of the world, not just the United States. In January, he called the Arctic island "imperative" for national and world security, asserting that no other nation or group of nations is in a position to secure it.

Beyond Greenland, Trump has expressed interest in acquiring Kharg Island from Iran. Located 15 miles from Iran’s coast, the island handles nearly 90% of Iran’s crude oil exports. Additionally, Trump has suggested that Canada could become the 51st US state.

Market Probabilities

Bettors on Kalshi have assigned varying probabilities to US territorial expansion based on specific timelines. The market sentiment reflects skepticism regarding the feasibility of these acquisitions within the near future.

On Tuesday, Trump posted a photo on Truth Social showing him in the Oval Office with European leaders. The image included a map displaying Canada, Greenland, and Venezuela with the American flag imposed on them.

Shark Tank investor Kevin O'Leary stated that future conflicts will be defined by artificial intelligence, precision weapons, and advanced defense systems. He argued that these technologies allow the U.S. to pressure adversaries without relying on traditional large-scale warfare. O'Leary emphasized that this shift reduces the necessity for widespread casualties while maintaining strategic compliance.

O'Leary Details AI-Powered Warfare Strategy

In a post on X on Tuesday, O'Leary described a future warfare strategy he termed "tenderization." He argued that AI-powered systems could allow countries to weaken an opponent’s capabilities through sustained, targeted pressure. "If Iran doesn’t want to play ball, they will be tenderized into compliance," O'Leary wrote.

He explained that the approach involves "highly specific ordinance, satellite-controlled, AI-driven, predictive analysis on everything you need." O'Leary noted that these technology and operations would be managed from U.S.-based infrastructure. "You don’t have to kill a lot of people. You don’t wanna do that," he said, arguing that precision weapons and AI could reduce the need for traditional warfare methods. "This is going to be a new type of warfare. This is called tenderization," he added.

O'Leary also called for greater investment in AI-powered defense systems. "That’s what we need in America. That’s what I’m building, and that’s what every other developer’s gonna have to build," he stated.

AI Reshaping Cybersecurity And Modern Warfare

Earlier, the Five Eyes intelligence alliance warned that rapid AI advances could accelerate cyberattacks. The alliance stated that adversaries could use AI to identify vulnerabilities, generate malicious code, and automate operations faster. They urged organizations to prepare within months rather than years.

XTEND CEO Aviv Shapira said the future of defense technology could rely on AI-powered platforms. These platforms would connect drones, robots, and autonomous systems across manufacturers. Shapira described XTEND’s vision as an "Android of robotics" designed to unify defense hardware through software.

Palantir CEO Alex Karp said AI was providing the U.S. and its allies with a strategic advantage. He argued that AI was transforming modern warfare by improving intelligence sharing and battlefield coordination amid rising Middle East tensions.