Goldman has a humorous writing style and for comic effect he often uses exaggerated analogies when describing players' skills. He is bold in criticizing decisions of general managers and coaches and humorously deriding them.

In his writings on the YES Network and the Sun, he criticized Yankees manager Joe Torre for moves that he thought cost the Yankees the World Series. He repeatedly claimed that one of Torre's major mistakes in the 2003 World Series was when in Game 4 in the 11th inning Torre inserted Jeff Weaver, who had not pitched in more than 12 days, as the relief pitcher instead of the Baseball Hall of Fame candidate and closer Mariano Rivera. Rivera was considered the best closer of all time and is the all time Major League postseason leader in saves and ERA. He was also considered the best postseason relief pitcher of all time. Instead, Weaver gave up a walk-off home run in the 12th inning to the Florida Marlins' Álex González. Goldman also attributed partial blame to both Torre and hitting coach Don Mattingly for the Yankees' playoff losses in 2004 and 2006. During both the last four games of the 4-3 loss in the 2004 American League Championship Series to the Boston Red Sox and the 3-1 loss in the 2006 American League Division Series to the Detroit Tigers, Goldman claims the Yankees did not hit well because they were not patient at the plate, unlike during the regular season.

One of Goldman's themes is the Yankees' lack of success in developing young pitchers. He attributes it partially to the Yankees' expensive free-agent acquisitions that cost them draft picks, but he also notes how at times young pitchers who struggled with the Yankees were traded to other teams and fared better there, and even sometimes won a World Series with the new team. He suspects that lack of skill and impatience in coaching are the causes.

Another theme in Goldman's writings is the Yankees' lack of young pitchers in recent years. He mentions that during the 2003-2004 off-season, Roger Clemens, Andy Pettitte and David Wells all left the Yankees as free-agents to pitch for their hometown teams, and after that the Yankees' pitching deteriorated, though both Pettitte and Clemens were again with the Yankees in the 2007 season (Clemens joining only halfway through the season).

Bernie Williams

Goldman was a fan of Bernie Williams during his peak but after the 2006 season believed Williams was no longer the player he once was and should not take at-bats away from the young fourth outfielder, Melky Cabrera. His skepticism about Williams brought upon him the criticism of Yankee fans who remembered Williams at his peak when the Yankees won four World Series. Williams was, in fact, dropped from the Yankees lineup.

Alex Rodriguez

Goldman stands out as a staunch supporter of Yankees third baseman Alex Rodriguez who went through fielding and hitting slumps in the 2006 regular season and did not hit well in the post-season as a Yankee since game 3 of the 2004 ALCS. Goldman repeatedly rebuffed his critics and was strongly against trading Rodriguez, despite the rumors circulating in the 2006-2007 off-season that Rodriguez would be traded. Goldman claimed that even if Rodriguez were traded for someone of equivalent value, the Yankees would deteriorate in hitting because of a downgrade at third base. The only third basemen who was then hitting better than Rodriguez were the Mets' David Wright and the Marlins' Miguel Cabrera. Rodriguez went on in 2007 to win the Most Valuable Player Award in the American League, though once again his performance in the playoffs was disappointing.

Goldman frequently engages in non-baseball-related discussions on topics of food, music, American history, politics, and obscure movies, writing at length about those topics in the Pinstriped Blog and his chats on Baseball Prospectus.com. He is also a vocal critic of President George W. Bush's administration and its decision to send troops to Iraq. He occasionally writes about politics in the Pinstriped Blog and refers to it in the Sun. There has been no reported conflict between him and the Sun's conservative editorial board.

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.

Goldman has both Jewish and French ancestry. He is a graduate of East Brunswick High School and Rutgers University.