[3] Webb was educated at King High School and Hillsborough Community College, Tampa, Florida, in the United States.

During Webb's time as CIFA President, it was reported that British players were being offered up to £70k to represent Cayman Islands at international football.

[7] Webb was unanimously elected to lead the Confederation of North, Central America and the Caribbean Football Association (CONCACAF) on May 23, 2012, in Budapest, Hungary.

Webb appointed a new Miami-based General Secretary, Enrique Sanz de Santamaría, enabling the CONCACAF head office to relocate to Miami.

The indictment, which named fourteen other individuals related to FIFA, included racketeering, wire fraud and money laundering conspiracy.

Other football officials charged are Eduardo Li, Eugenio Figueredo, Jack Warner, Julio Rocha Lopez, Costas Takkas, Rafael Esquivel and Nicolás Leoz.