The Winter Meetings have been Organized Baseball's annual offseason ritual since the early days of the game. This is SABR's second volume on their history, covering 1958 - 2016, plus a special section on the Negro Leagues winter meetings. The latter years of the 20th century included many monumental changes in the business of baseball. This volume covers multiple rounds of expansion, the advent of free agency, several work stoppages, collusion among the owners, and the elimination of the American and National League presidents' offices and consolidation of the two leagues as a single business entity.

With contributions by 40 members of the Society for American Baseball Research: Abigail Miskowiec, Andy Bokser, Bob Whelan, Chad Hagan, Charles H. Martin, Chip Greene, Chris Jones, Christopher Matthews, Clayton Trutor, Dan Levitt, Darren Munk, David M. Kritzler and Alan P. Henry, Donald G. Frank, Duke Goldman, Gregory H. Wolf, Hawkins DuBois, Jason C. Long, Jason Myers, Jeff Barto, Jerry Swenson, Jessica Frank, John Bauer, John Burbridge, Kent Henderson, Luca Rossi, Mark Armour, Mark S. Sternman, Michael Huber, Mike Lynch, Paul D. Brown, Paul Hensler, Robert K. Whelan, Rodger A. Payne, Ross E. Davies, Steve Cardullo, Steve Weingarden, Steve West, Tim Rask, Tom Cuggino, Wayne G. McDonnell, Jr.