"I wish I had a bigger position than I have, but it's a sizable position. ... It's in the hundreds of millions of dollars, but it could be more but the stock just got away from me," he said Monday on CNBC's "Halftime Report." "I added to the position. I also bought the tracking stock [Dell Technologies Class V] too, which I don't think was mentioned."
CNBC reported in April that Icahn acquired a "medium-sized" stake in VMware, according to sources familiar with the matter. Dell is considering a reverse merger with VMware where it would also consolidate the tracking stock (ticker DVMT) as part of a deal. Dell said last week it was considering an exchange of its closely-held DHI shares for DVMT shares, which track the performance of VMware within Dell.
Icahn broached the prospect of facing off again with Dell's founder, Michael Dell.
"We're right there against Dell again, maybe," he said. "I say maybe because I hope he does the right thing and he pays a fair price for it."
Icahn publicly and unsuccessfully challenged Michael Dell in his 2013 effort to take Dell private. Michael Dell and Silver Lake ultimately acquired the company for $24.4 billion, a price tag Icahn said "greatly undervalues it."
Icahn's ownership of both the tracker stock and VMware suggests he is bullish on the prospect of a deal between Dell and VMware. Dell is currently seeking feedback from holders of the Class V shares about terms of a potential VMware deal that would satisfy investors, CNBC reported last week.
The billionaire investor is chairman of Icahn Enterprises. He often targets struggling companies as an activist to bring about changes to improve their businesses and boost their stock market values.