On January 18, 2008, Holliday signed a two-year, $23 million contract with the Rockies, covering his final two years of arbitration. The Rockies also offered a four-year, $72 million extension, with a club option for a fifth year at $12 million. The team viewed the contract extension with the two years covering arbitration as a singular deal worth approximately $107 million. In contrast, Holliday and his agent, Scott Boras, regarded the extension as an $84-million free agent contract undervalued compared to similar players. Therefore, negotiations stalled in spring training.