This chapter examines the innovations of “Liberty Printer” John Holt as well as his heated rivalry with loyalist printer James Rivington. An organ of the Sons of Liberty, Holt’s New-York Journal orchestrated America’s first news distribution service, which publicized British abuses in Boston, helping unite the colonies against a new, common enemy. With the arrival of the British in 1776, Holt would print his newspaper, sporadically, on the run. These wartime issues reveal the chaos of war as well as Holt’s own dire straits as he continued to serve his constituents. In James Rivington, Holt found an equally talented rival. Rivington’s Gazetteer was a modern marvel, which served the Tory cause as fervently as the Journal served the Patriot cause. In examining the parallel lives and prints of Holt and Rivington, this chapter showcases their modern print innovations, elicits a sharper understanding of the role of wartime propaganda, and interrogates the complicated decision of allegiance for Loyalists, Patriots, and the many Americans who remained neutral throughout the duration of the war.