Bruce Robert Berkowitz (born circa 1958 in Chelsea, Massachusetts, to working-class parents—father Barney Berkowitz, who ran a corner grocery store with bookmaking and taxi driving, and mother Hennie) is an American value investor. He is the founder, Chief Investment Officer, and Managing Member of Fairholme Capital Management LLC (established 1997 in Short Hills, New Jersey; relocated to Miami, Florida by 2006), and President and Director of Fairholme Funds, Inc. (The Fairholme Fund launched 1999). Renowned for concentrated bets on undervalued assets, including early investments in WorldCom debt, Sears Holdings, and heavy stakes in Fannie Mae and Freddie Mac, where he led shareholder legal challenges against the U.S. government's conservatorship. Berkowitz received Morningstar's Domestic-Stock Fund Manager of the Year (2009) and of the Decade (2000-2009) awards, and Institutional Investor's Money Manager of the Year (2013). He has served on boards including Chairman of The St. Joe Company (2011-2024), Sears Holdings (2016-2017), White Mountains Insurance Group (2004-2010), and others. In 2014, he proposed a Miami museum for Richard Serra and James Turrell artworks, approved in 2015. Berkowitz worked in his family store, quit high school briefly at 15 to manage bookmaking during his father's heart attack, attended Chelsea High (one year), Huntington Prep, and Beaver Country Day School. The first in his family to attend college, he earned a BA in Economics from the University of Massachusetts Amherst (1980), marrying wife Tracey Pellows the same week; they have three children (two sons, one daughter). Post-graduation, he joined the Strategic Planning Institute (Cambridge, MA), then Merrill Lynch (London, 1982/1983), Lehman Brothers (London 1986, New Jersey 1989 as Senior Portfolio Manager), and Smith Barney (Managing Director 1993-1997). Berkowitz's philosophy emphasizes cash generation, human psychology from his upbringing, and contrarian bets on sectors like defense, healthcare, infrastructure, and survivors like Hertz. His fund has faced volatility, with recent heavy concentration in St. Joe Company (82% in 2023 reports), and setbacks in Fannie/Freddie and Sears real estate plays.