For the first 24 hours of the trade deadline, the Giannis Antetokounmpo situation caused equal parts confusion and relief. That changed after a different kind of offcourt move. A prolific investor, Antetokounmpo is expanding his portfolio once again, but his latest venture has sparked an uncharacteristic wave of criticism from fans and league observers alike.

His latest investment comes when he decided to stay put in Milwaukee. Now many believe that his investment and his team decision aren’t mutually exclusive.

Giannis Antetokounmpo announces major investment

The Milwaukee Bucks’ star’s company, Ante Inc., invested in Kalshi, a federally regulated prediction market that allows users to trade on the outcome of real-world events, ranging from economic indicators to political elections. It’s not a completely new investment for Ante Inc. that has ventured into real estate, fintech, and AI-related content production.

Details of his stake aren’t disclosed, but the fact that he has even a point percentile in this puts him in a precarious position. The NBA has not really accepted the prediction market industry though Kalshi has a partnership with the NHL and golfer Bryson DeChambeau. They’ve not responded to his move but Kalshi and Giannis did.

“I love the Kalshi markets and have been checking them often recently,” Giannis Antetokounmpo said in the press release. “I like to win. It’s clear to me Kalshi is going to be a winner and I’m excited to be getting involved.”

“As an active player in the NBA, Antetokounmpo will be forbidden from trading on markets related to the NBA, per Kalshi’s strict terms of service that ban insider trading and market manipulation,” Kalshi said in the press release. The issue, however, is that fans think that this venture is not completely free of conflicting interests.

Besides the ethical gray area, the recent events have made the NBA community feel disillusioned by his business move.

Giannis Antetokounmpo’s trade saga comes under a magnifying glass

The controversy stems from a sequence of events over the past several months regarding Antetokounmpo’s future in Milwaukee. Injuries and oncourt incidents made fans think he’s mentally checked out of Milwaukee. Trade speculation was fueled by his open desire to join a team like the Knicks and the Warriors’ active pursuit of it.

While his agent was supposedly in talks with the Bucks front office, Giannis presented a confusing stance. He’d claim his agent is negotiating his future autonomously while declaring his intent to stay in Milwaukee. Doc Rivers also would repeatedly shut down trade buzz.

The trade deadline passed anticlimactically. Two of the biggest pieces, Giannis Antetokounmpo and Ja Morant stayed with their teams as if the last few months didn’t happen. The team even took potshots at Shams Charania when Giannis stayed.

While most were on the Giannis trade watch, the narratives drove massive volume on Kalshi. After news of Giannis’ investment surfaced, Kalshi users revealed the market the app was running on Giannis. Users were forecasting whether Antetokounmpo would request a trade or sign an extension with the Bucks. According to platform data, users wagered a staggering $23 million on these outcomes.

With Antetokounmpo ultimately deciding to remain in Milwaukee and subsequently revealing himself as a major stakeholder in the very platform that profited from the speculation, the backlash was instantaneous. Fans who were emotionally and financially invested in the trade saga felt his career uncertainty was weaponized for profits.

On social media, fans have labeled the move “gross,” with one prominent commentator noting, “You can’t just take money from anything and expect people to give you the utmost respect.”

Because details of the investment aren’t disclosed, it’s unclear if Giannis profited off this at all. It’s also unknown when he invested, although the window between the trade deadline and the announcement is small.

Despite the outcry, there has been no formal indication that the NBA will look into the partnership. Current league collective bargaining agreements are often vague regarding investments in non-sports gambling entities.