The Blue Guidon The Newsletter of Andover and the Military
Fall 2025
John Campbell Greenway By David Chase, Faculty Emeritus
“The best man in my regiment.” That was Theodore Roosevelt’s assessment of John Campbell Greenway, a Rough Rider during the Spanish-American War. Born in 1872, Greenway would excel in three endeavors: as an athlete, mining executive, and Army officer in two wars. In each undertaking, courage, skill, teamwork, initiative, and determination played their part. John Campbell “Jack” Greenway entered Andover in 1891. He first achieved recognition as a member of PA’s football team, playing left end. In 1892 he was catcher on the baseball nine. Both teams had mixed records, but (as today) the school judged a season successful if PA trounced Exeter, and it had. It was common for Andover students destined for scientific or technical vocations in the late 19th century to leave before graduating. Greenway was among 13 underclassmen matriculating into Yale’s Sheffield Scientific School in 1892. At Yale, he gained national recognition, again in football, playing end, and in baseball as catcher. Yale teams were among the best of the era, each game reported in papers across the country. Elected president of his class, Greenway graduated with an engineering degree in 1895. He went to work for Carnegie Steel at its thrumming Duquesne mill on the Monongahela outside Pittsburgh, starting as a machinist’s helper at $1.32 a day. He spent two and a half years
gradually advancing, proving himself a bright, ambitious employee. Late in April 1898, with the United States’ declaration of war against Spain, Greenway left Carnegie, took the train to San Antonio, and enlisted as a trooper (private) in the First United States Volunteer Cavalry, soon nicknamed the Rough Riders. Col. Leonard Wood was commander. Wood had been a college football player himself in the early 1890s and recalled Greenway’s Yale career. Thanks to Wood, in four days Trooper Greenway became 2nd Lt. Greenway. The Rough Riders were equipped with the latest Krag-Jørgensen carbines and Colt revolvers. They were fitted with a unique, casual uniform, rugged and frontier-like: a large, high-crowned slouch hat, flannel shirt, baggy canvas trousers, leggings, boots, a cowboy bandana worn around the neck. Supplying the regiment was the work of Wood’s second in command, Lt. Col. Theodore Roosevelt. More than a thousand Rough Riders assembled in Tampa in May 1898. Due to a lack of adequate sea transport, however, only eight companies, without their mounts, arrived in eastern Cuba on June 23. The Rough Riders would fight as infantry. The troop ships heading to Cuba also carried Regular Army Cavalry, African American Buffalo Soldiers, and volunteer Black troops. (Among them was Lt. Walter Pinchback, PA Class of 1893, profiled in the fall 2023 issue of The Blue Guidon.)
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July 1898: The Rough Riders atop San Juan Heights during the Spanish-American War. Theodore Roosevelt is center; Jack Greenway is literally Roosevelt’s right-hand man.