Immediately before he was appointment Chief of Staff to Governor Scott, Hollingworth served as CEO of Parallel Infrastructure, a division of Flagler Development.
Flagler, a
real estate development company, owns some 19,000
acres of property and more than 50 office and industrial buildings in
Jacksonville,
Orlando,
Fort Lauderdale, and
Miami. Its parent company,
Fortress Investment Group, also owns
Florida East Coast Railway, which provides freight service on tracks running through coastal communities from Jacksonville to Miami. In 2014, a related company, All Aboard Florida (parent company:
Florida East Coast Industries), attempted to secure a $1.6 billion federal government loan to finance the development of
Brightline, a
higher-speed passenger train service between Orlando and Miami on these tracks. This plan, which entails the state of Florida financing the construction of a new $213 million transportation center at the
Orlando airport to house the
terminus of the rail service, is subject to widespread opposition by local governments in communities north of
Palm Beach County where it will pass through but not provide service. The fact that Hollingsworth was previously connected with Flagler and is now the governor's "right-hand man" has raised concern over possible
conflicts of interest in the All Aboard Florida plan. Hollingsworth worked for
CSX from May 1995-May 2000 and from February 2002-September 2004. He was vice president of
APCO Worldwide from 2000-2001. On December 10, 2013, under pressure from journalists, Hollingsworth released a statement to the
Miami Herald and
Tampa Bay Times that he had lied in his 2011 application for membership in the board of
Enterprise Florida Inc., the State of Florida's public-private economic development agency. On his application, he claimed that he graduated from the
University of Alabama with a BA in Communications in 1990, when in reality, he didn't obtain the degree until 2009. Hollingsworth has worked for the following Florida politicians:
Charles Bennett,
Corrine Brown,
Ed Austin, and
John Peyton. ==Personal life==