ESPN’s senior NFL insider Adam Schefter is among the early investors benefiting from the recent sale of Underdog, a fantasy sports and prediction market company. The business was acquired by the U.K.-based online trading firm IG Group for up to $2.15 billion, including $1.1 billion upfront and additional earnouts based on future performance. Schefter had initially invested in Underdog back in 2021 during a $10 million funding round that also included high-profile investors like Mark Cuban, Kevin Durant, and Jared Goff.

Although the exact amount of Schefter’s investment was small and undisclosed, industry sources speculate that the value of his stake has at least tripled since Underdog was valued at $485 million following its Series B funding round in 2022. Despite this financial success, Schefter has not increased his involvement with the company beyond this early investment and has no ongoing operational role. Underdog’s recent sale underscores the growing appetite in the fantasy sports market, drawing interest from major financial firms like IG Group.

Underdog’s sale includes $1.1 billion paid upfront to shareholders, a $200 million earnout for Underdog shareholders, and up to $850 million earmarked for eligible employees dependent on the company’s future performance. The acquisition marks a major milestone for the company, which has leveraged its position in the burgeoning sports prediction space to attract significant investor attention and capital. IG Group’s acquisition positions it to deepen its foothold in the fantasy sports and trading markets.

Around the same time he invested in Underdog, Schefter also backed Boom Entertainment, a firm that develops sports and casino gambling apps, though it’s unclear if he retains a stake there. Schefter recently extended his ESPN contract, continuing his prominent role in sports media while benefiting from these early-stage investment wins. This latest success reflects how sports insiders like Schefter can strategically capitalize on emerging opportunities within the intersecting worlds of sports, gaming, and digital marketplaces.