Handpicked Skeptic to Pitch Hardball Questions at Warren Buffett

“It’s fair to say that I’m Daniel in the lion’s den,” Douglas A. Kass, the head of Seabreeze Partners Management, said on Thursday in the middle of his trip to Nebraska. “But I’ve prepared intensely.”

The addition of Mr. Kass, who is Berkshire’s first credentialed bear and is betting that the company’s stock will fall, is the latest adjustment to a formula that has been in place for decades. More than 18,000 shareholders flock to Omaha in early May every year, hoping to listen to what one of the country’s most celebrated investors has to say.

Most years, shareholders have asked a wide range of largely softball questions, from the billionaire’s thoughts on the global economy to his religious beliefs.

But Mr. Buffett has tried to toughen up the questioning at the annual meeting, a 180-degree turn from what the majority of publicly traded companies seek to do. He has asked reporters,In home display  including one from The New York Times, and analysts to ask tougher questions.

Inviting Mr. Kass, 64, is perhaps the boldest move yet. The hedge fund manager is best known for his frequently contrarian positions, often on display in appearances on television shows about business and in his column. Mr. Kass has also pointed to his time working for Ralph Nader while a student.

“See if you can drive the stock down 10 percent,” Mr. Buffett teased his new foil during a CNBC interview in March.

Mr. Kass has repeatedly explored Berkshire’s weaknesses over the years, including a 2008 article. Among his arguments at the time were Mr. Buffett’s advanced age and the company’s slowing growth.

Mr. Kass maintains a short position on Berkshire’s shares, whose size he declined to disclose other than to describe it as average-size for him. But he spent the last month reading up on Mr. Buffett and his company,Home energy management  and as of Thursday was winnowing 25 potential questions down to six.

Two, he contended, would generate big news if Mr. Buffett answers them. The others have not been asked before, he said.

All the while, Mr. Kass said, he has remained an admirer of Mr. Buffett, sometimes referred to as the Oracle of Omaha. Since beginning his research, manager Mr. Kass has found a number of similarities with Mr. Buffett. For example, both have been treated for prostate cancer, and both once collected discarded horse-racing tickets at tracks in their younger days.

For his first trip to the Berkshire meeting, Mr. Kass is bringing his son and a group of friends.

“I’m psyched,” he said. “It’s like the financial World Series to me.”

Apart from Mr. Kass, many elements of previous Berkshire meetings will be in place again this year. Mr. Buffett, 82, is likely to reiterate that his company — a huge conglomerate that counts railroads, private jets and running shoes among its holdings — has a succession plan in place for when he finally hangs up his investor’s hat.

He will also most likely discuss his hunger to strike more big deals, one of his signature corporate moves. Neither of his acquisitions this year appears to qualify for the giant takeovers he craves: Berkshire teamed up with a Brazilian investment firm to buy H. J. Heinz for $23 billion, and it bought the 20 percent of the Israeli tool maker IMC that it did not already own for about $2 billion.

“It’s back to work; Charlie and I have again donned our safari outfits and resumed our search for elephants,” Mr. Buffett wrote in his annual investor letter, referring to his longtime investing partner, Charles T. Munger, Berkshire’s vice chairman.

He is also expected to discuss his recent newspaper buying spree, having bought 28 dailies over the last year and a half for $344 million. While the acquisition campaign is not the most expensive he has ever conducted, Power monitor Mr. Buffett has described himself as an addict who sees value in local news.

It is unclear whether he will be asked about another new move: into social media. On Thursday at 11:20 a.m. Omaha time, Mr. Buffett overcame a famous aversion to technology by posting his first message on Twitter. “Warren is in the house,” he wrote as a camera for Fortune magazine hovered over his shoulder, capturing every tap.

By late afternoon, his post had been reposted more than 25,000 times, and his nascent Twitter account had drawn 176,000 followers. Among them is Mr. Kass, a prolific user of Twitter who has been documenting his passage to Omaha.

The foray was a surprise, given that Mr. Buffett once claimed he missed an important message about Lehman Brothers because he did not know how to check his phone’s voice mail.

“I guess he’s not as much of a Luddite as he professes,” Mr. Kass said.

Mr. Buffett dryly hinted that Twitter had a little more in its favor than other platforms.

“The co-founder came from Nebraska,” he said, in an apparent reference to a Twitter co-founder, Evan Williams. “So it can’t all be bad.”