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Goldman began his career doing profiles for Yankees Magazine, a writing job that eventually led to the creation of one of the first online Yankees blogs, "The Pinstriped Bible" in 1999. The blog eventually became affiliated with the Yankees' YES Network website, as both and the original title and "The Pinstriped Blog". Goldman was also hired by Baseball Prospectus to write for them, and he edited or co-edited several volumes of the Baseball Prospectus annual. He eventually became the Editor-in-Chief of BP and wrote the "You Could Look it Up" columns for the site during the season. In December 2011, he was selected as a BP representative in the Baseball Writers Association of America. Goldman left both BP and YES Network in 2012 to join colleague Rob Neyer at the sports site SB Nation.
Goldman edited BP's books Mind Game (2005 — ISBN 0-7611-4018-2) and It Ain't Over 'til It's Over (2007 – ISBN 0-465-00284-6), as well as authored his own book Forging Genius: The Making of Casey Stengel (2005 — ISBN 1-57488-873-0) (2006 — ISBN 1-57488-874-9). He also co-edited the 2006, 2007 and 2008 editions of the Baseball Prospectus annual.