Billionaire investor Carl Icahn widened his exposure to energy-related holdings in the second quarter, according to regulatory filings Monday.

Icahn, known as a corporate activist who holds his shares through various funds, aggressively boosted his stake in Chesapeake Energy Corp. (CHK) and reported new investments in NRG Energy Inc. (NRG) and Anadarko Petroleum Corp. (APC), as of June 30.

At that time, Icahn owned 12.7 million shares of Chesapeake Energy, up from 2.1 million shares at the end of March. The holdings give him a 2% stake in the natural-gas company and place him among the top-10 shareholders. He reported his initial investment in the company last quarter.

In the latest quarter, he reported a new two-million-share stake in oil and natural-gas company Anadarko, amounting to less than 0.5% of the company, and a 2.4-million-share investment in power producer NRG Energy, a 1% holding.

Icahn also showed activity in the technology sector, where he has been active in the past. He reported a 9.5-million-share holding in Lawson Software Inc. (LWSN), or a 5.9% stake. On June 8, Icahn had filed that he beneficially owned 15.6 million shares of the company, with some portion of that being in call options.

Icahn reported a 7.8-million-share investment in chip-design software company Mentor Graphics Corp. (MENT), a 7.3% stake. In July, Icahn reported that he beneficially owned 14 million shares of the company, with a portion being call options.

In both cases, he has called the stocks undervalued and said he wants to meet with management.

He reported a new stake in Micro Systems Inc. (MCRS) of 654,960 shares, amounting to less than 1% of the total outstanding.

Icahn also reported a new 2.4-million-share stake in Smith & Wesson Holding Corp. (SWHC), equaling about 4% of the firearms maker.

In the period, Icahn reported no change to his biotechnology holdings, including stakes in Biogen Idec Inc. (BIIB), Genzyme Corp. (GENZ) and Amylin Pharmaceuticals Inc. (AMLN), all companies in which he has board representation.

He reported no stake in Adventrx Pharmaceuticals Inc. (ANX) after having a 4.3-million-share investment, or 30% of shares outstanding, in the small specialty pharmaceutical company last quarter.

Monday's disclosures don't include a complete picture of Icahn's holdings because he has been permitted to keep some of his investments confidential. Prominent investors are sometimes permitted to temporarily withhold information from their quarterly reports if the disclosure would interfere with an investment strategy.

Some of the holdings reported on Icahn's 13-F are outdated, because he often buys more than 5% of companies' outstanding shares, forcing him to make more frequent filings regarding those holdings.

Since the end of the second quarter, Icahn exercised options to increase his stake in Hain Celestial Group Inc. (HAIN) by two million shares, bringing his total ownership to 5.65 million shares, or 13.8% of shares outstanding. Icahn reached a deal with the food company to put two people on its board, including his son Brett.

Meanwhile, Icahn is trying to take over Lions Gate Entertainment Corp. (LGF) and recently extended his tender offer of $6.50 a share until Oct. 22, as he fights the film studio in Canadian court. He is attempting to block a July debt-to-equity swap that essentially shrinks his stake in Lions Gate as it tries to thwart the buyout effort.

Earlier this month, Icahn bought 10.2 million shares of Motorola Inc. (MOT), a telecommunications company that is preparing to split itself in two. The purchase boosted his stake to a total of 232.2 million shares, or 9.99% of shares outstanding.

Icahn has sharply increased his stake in recent months, as some have speculated that he sees Motorola's value rising when it completes its split, which is set for early next year. At the end of 2009, he owned 119.8 million shares.

Many investors that manage more than $100 million are required to file 13-Fs with their stock holdings 45 days after the end of a given quarter, giving the public its freshest possible glimpse into the portfolios of well-known money managers. Most hedge-fund managers and others wait until the last possible moment to make these filings.

-By Thomas Gryta, Dow Jones Newswires; 212-416-2169; thomas.gryta@dowjones.com

 
 
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