Quoted in the "New York Times", a Pritzker family friend observed Pritzker was trapped in a deal of her uncle's making: "Penny got sucked into this…this was really the legacy of Jay." In 1995, Penny was named as one of three successors to the retiring Jay Pritzker besides his son Tom and his cousin Nick. Tom was named the official head of the businesses, Nick and Penny each named vice-chairman. Together, the three were to oversee the Pritzker family assets. Jay intended to keep the family business together, devising a system of trusts that would allow individual family members to receive money from the trusts to meet their needs; however, the family's wealth was to be primarily maintained in the trusts to grow the businesses and fund philanthropic endeavors. The Pritzker business empire contained over 200 businesses and was valued at $15billion. After Jay Pritzker's death in 1999, other Pritzker family members challenged Tom, Nick, and Penny's control of the businesses in multiple lawsuits. Penny's brothers joined in one of the lawsuits. In 2001 Tom, Nick, and Penny decided to sell family assets to allow eleven cousins to receive a share, dissolving the family's business ties. Disentangling the family's business interests took nearly a decade. The family sold its controlling stake in the Marmon Group to Berkshire Hathaway for $4.5billion in 2008. The Pritzker Realty Group sold Parking Spot, an airport parking management business Penny co-founded in 1998, to Green Courte Partners LLC for $360million in 2011. Starting in 2005, she served as non-executive chairman of TransUnion. In 2009, she co-founded Artemis Real Estate Partners LLC, a real estate investment management company, with Deborah Harmon. In 2011, she founded an investment office, PSP Capital Partners. Altogether, Pritzker started five companies before joining the federal government. Pritzker's friendship with Barack Obama and his family dates back to the 1990s when he was a professor at the University of Chicago. Pritzker met Obama at a Chicago YMCA where her son participated in a basketball program coached by Obama's brother-in-law Craig Robinson. Obama and his family were frequent guests at Pritzker's Lake Michigan vacation home. Pritzker was an early supporter of Obama's political career, helping to finance his 2004 Senate campaign. Early in the Democratic presidential primary, Pritzker's financing helped Obama's candidacy survive when Obama was trailing Hillary Clinton in the polls.