Just thought I would post some interesting background information.

Buster Olney arrived at ESPN after six years at the New York Times covering the Mets and Yankees

Not with ESPN anymore but Peter Gammons grew up in Groton, Massachusetts, and lives in Boston. Gammons covered the Red Sox at the Boston Globe for many years.

Keith Law grew up in Smithtown, New York and graduated from Harvard University

Karl Ravech grew up in Needham, Massachusetts and was previously affiliated with local radio stations in Pennsylvania and New York.

Bill Simmons grew up in Massachusetts and studied print journalism at Boston University. Before ESPN he worked on the website Digital City Boston, worked for the Boston Herald and was known as the “Boston Sports Guy”

Other Notables

Tim Kurkjian grew up in Maryland and covered the Baltimore Orioles for the Baltimore Sun

Jayson Stark was born in Philadelphia, Pennsylvania, and prior to joining ESPN he covered the Philadelphia Phillies for The Philadelphia Inquirer.
He not there anymore but Steve Phillips was the General Manager for the New York Mets.

Most of the rest of the ESPN’s baseball contributors are ex-players.