Buffett fears Berkshire's five-year book value growth rate may underperform the S&P 500 for the first time ever. In 2012, Berkshire's book value per share increased 14.4%, behind the S&P 500's gains of more than 15%. In a twist to the shareholder meeting, Doug Kass -- head of Seabreeze Partners and a contributor at TheStreet -- will present a case for shorting shares of Berkshire Hathaway. While Kass will certainly have room to make an argument, and he could even borrow Buffett's words, shorting Berkshire Hathaway shares has made for a disastrous trade over multiple decades. Kass, who said he is shorting Berkshire's Class B shares and is slightly underwater since initiating the position about a month ago, has bet against the "Oracle of Omaha" before. In March 2008, Kass wrote an article for TheStreet outlining 11 reasons to short Berkshire shares. Subsequently, Berkshire shares fell about 40% amid a collapse in the U.S. financial sector. On Saturday, Kass toldTheStreet his participation as a Berkshire bear will add a novel element to the annual meeting. " Warren Buffett was probably feeling the questions were getting a bit redundant... I think he wants to be challenged," Kass told TheStreet. "I have one big challenge for him, which I think will reverberate the auditorium," Kass said. Kass's participation at Berkshire's shareholder meeting may also underscore investor concerns about the direction of the company such as management transition and a deployment of the company's cash stockpile. "I think the succession question will be obviously front and center," said Thomas Russo, a partner at Gardner, Russo & Gardner in an April interview. "I gather there will be some commentary." In late 2011, Buffett also said his son, Howard Buffett, would succeed him as a non-executive chairman of Berkshire to oversee a maintenance of the firm's values. Less clear is who would be chief executive of Berkshire Hathaway. Currently, speculation centers on insurance unit head Ajit Jain, BNSF railroad CEO Matthew Rose, MidAmerican Energy CEO Greg Abel as leading candidates to be Buffett's successor. Buffett has informed Berkshire Hathaway's board of directors of his successor. Russo, the Berkshire investor, sees room for multiple job openings to replace Buffett, when the time comes. He expects up to four roles to fit the shoes of Buffett. Gardner, Russo & Gardner is Berkshire's tenth largest shareholder with a stake of nearly $800 million in the company's Class A shares and over $200 million of Class B shares, according to Bloomberg data. Russo says Berkshire holding's represent about 11% of the firm's assets.