Winchester Osgood

Winchester Osgood cabinet photo, signed on the reverse (circa 1893)

“Who’s good, He’s good…Osgood”.  A frequent rally cry by the Quaker faithful which rang across the University of Pennsylvania's Manheim  Field in the late 19th century.   The whole University student body was so devoted to this spectacular athlete the cheer was even shouted during Sunday Chapel under the Provost’s nose.  Yet in the fall of 1896 the sound of adoring fans in Winchester Osgood’s ears was deafened by the exploding forty-three caliber shells from a Hotchkiss revolving cannon and the battle cry of “Vive, vive Cuba Libre”.  His football pads and cleats exchanged for an Officer’s uniform for the volunteer Cuban Liberation Army.  While the field of action once on the University of Pennsylvania campus was now on the mosquito infested swamps of Havana Cuba his valor, honor and courage were consistent throughout.  But as he “slept in his hammock at night, with his revolver round his waist and the stars of heaven overhead,” Winchester Osgood dreamt of being at home, going to Catholic service with the minister sprinkling holy water, only to awake and find dew drops falling on his war torn face.  How did he end up so far from home?

Winchester Dana Osgood was born in Fort Barrancas, Florida on April 12, 1870 to Henry Brown Osgood Jr and Harriet Mary (Hubbard) Osgood.  Fort Barrancas was a US Army Fort originally constructed by the Spanish in 1698, located physically within present day Naval Air Station Pensacola.  Henry Osgood was stationed there at the time of Winchester’s birth, rising to the rank of Brigadier General before his retirement on October 13, 1907 at the age of sixty-four.  Henry Osgood was the grandson of Judah Dana, Great Grandson of John Winchester Dana and Great-Great-Great Grandson of Dartmouth founder, Eleazar Wheelock.  Harriet Mary Hubbard was the daughter of sea Captain Richard Steer Hubbard and Amelia Douglas, who inherited the family farm which eventually became Win's childhood home.  After 250 years this farm is still maintained by the Douglas/Osgood descendants.

Winchester was one of five children and noted at an early age for his upright, generous and impulsive, though somewhat reserved independent spirit.  He attended preparatory school at Wesleyan Academy in Wilbraham, Massachusetts.  Wesleyan Academy was one of the oldest educational institutions of the Methodist Episcopal Church, established by New England clergyman in 1818.  It was intended for general educational purposes but also for young men intending to enter ordained ministry.  It was there that “Win” met Caroline Bushnell Davis.  Ms. Davis was noted as a “pretty little girl, with a roguish face, laughing eyes, and despite her tender years, a most proficient flirt”.  She preferred boys who were strong and athletic.  Young Osgood was just the opposite; shy, frail, and insecure.  Yet Osgood fell madly in love with her.  To win her affection there was only one thing for him to do – become a world class athlete.

Win Osgood with his sisters (Harriet and Emma), brother Henry (top right) and friends - circa 1895  

This wasn’t an easy task.  The other boys at school laughed at his feeble and awkward attempts.  On the football field he was pushed around like a rag doll.  Still he persevered, never losing sight of his ultimate goal.  All his spare time was spent in the gymnasium.  Slowly his muscles developed and grew.  During his last year at Wesleyan Academy he almost made the football team, but was determined too light.  The disappointment was bitter, but he consoled himself with the thought that he would enter Cornell next year along with Ms. Davis.  Maybe he could gain her affection there.

By the time Winchester entered Cornell, in the fall of 1888, he was a well-developed athlete.  He played right half-back for Cornell from 1888-89, 1891-92.  In the 1889 football game against Yale, Osgood was noted as the only man on the entire Cornell team who succeeded in running or dodging, scoring the only points for Cornell in a losing effort.   In 1892 the Big Red football team went 10-1 and outscored all opponents by a combined total of 432 to 54 under Carl Johanson.  Their sole loss was 20-14 against Harvard, where Osgood made practically all the points by Cornell and noted for his spectacular ability.  Winchester’s teammate that year was freshman Glenn Scobey Warner, who would go on to revolutionize the game as a player-coach.  Glenn Warner, affectionately referred to as “Pop”, would coach for 44 years and develop such innovations to include the single and double wing formations, the three-point stance and body blocking techniques.  He is best known for the youth football league he developed, which proudly still bears his name.

1892 Cornell football team

Also while at Cornell, Osgood rowed the bow oar on the Varsity crew, where he won the 1892 single-shell championship.  He won the boxing and wrestling championships.  He held multiple school records for the bicycle team and in 1892 he was awarded a medal as the best all-around athlete at Cornell.  In the midst of these demanding athletic commitments,  Win Osgood found time to join the Phi Gamma Delta fraternity and was actively involved in several school Christian youth groups.  Yet sadly, despite the admiration and accolades around campus, he couldn’t turn the head of the one student that mattered most - Ms. Caroline Davis.

After the 1892 Cornell football season, at mid-term, Winchester Osgood transferred to University of Pennsylvania despite his gridiron success and academic standing.  Osgood was a bit disappointed when Charles J. Barr was selected as captain for the 1893 football and crew teams, which some claim was the reason for his abrupt transfer.  Other reports state he was heavily recruited by Penn Hall of Fame coach George Washington Woodruff after coach Woodruff's mediocre 1892 inaugural season for the Quakers.  While possibly just a coincidence, Ms. Caroline Davis graduated Cornell in 1892 and returned to her home in Philadelphia that summer.

1894 University of Pennsylvania bicycle team

Osgood entered the civil engineering course at the University of Pennsylvania in the winter of 1892. At Pennsylvania, Osgood continued his dominance as a three-sport athlete, excelling at football, track and field, and wrestling. He lettered two seasons at halfback for the Quakers.  In his first year, he helped the 1893 football squad to a 12–3 record. The team had a strong start, winning its first 11 games. During that stretch, the defense only gave up 18 points while the offense scored 305 points. But Penn lost three out of the last four games to Harvard, Princeton and Yale.  Despite those loses Osgood received widespread recognition for his outstanding play, particularly in the 14–6 loss to Yale as he scored Penn’s only touchdown in the game.  In 1894, Osgood helped Penn to its first undefeated season. The 1894 team featured one of the greatest 19th century collegiate backfields – Arthur Knipe, George Brooke and Osgood. All three were named to Walter Camp’s All-American team.   The highlights of the season was a 12–0 victory over Princeton, only Penn's second win in 30 meetings with the Tigers, and an 18–4 victory over Harvard. Coach Woodruff once commented, “As a player Osgood has never been surpassed in his specialty of making long and brilliant runs, not only around, but through the ranks of his opponents.  After one of his seventy or eighty yard runs his path was always marked by a zigzag line of opposing tacklers just collecting their wits and slowly starting to get up from the ground.  None of them was ever hurt, but they seemed temporarily stunned as though, when they struck Osgood’s mighty legs, they received an electric shock.”  Pudge Heffelfinger, the legendary Yale All-American, gave this description of Osgood: "It was downright uncanny to watch him run, opponents missed him by inches. His body undulated like a snake's. He was the Red Grange of the pioneer era.”

1894 University of Pennsylvania football team

Win was the idol of spectators at a football match because of the unexpected things he did; however, he was also noted to be difficult to handle at times.  He would occasionally disregard signals if he had an opportunity to make a spectacular run, which indeed usually happened.  At times this individual play would be at a detriment to the team’s success.  It was likely for this reason he was passed over as captain for the Cornell teams in 1893.  This disregard of order, however, didn’t set well with the new Penn coach.  Woodruff benched Osgood on the sidelines for a game or two in 1893, which embarrassed and humbled him, but secured his understanding of team play for the Quakers.  Coach Woodruff was in charge, not his players, regardless of their superior talent and ability.  Osgood got the message loud and clear, developing a mutual love and admiration for his coach which continued after graduation.  At Penn Osgood also set collegiate two-mile bicycle records, won the 1894 middle and heavyweight national wrestling championship and received the collegiate heavyweight boxing championship.  He also excelled in tennis and baseball.   

Off the field he was a simple, wholesome, humble student that men around campus honored him even more.  Despite his tremendous physical strength, he had an almost feminine gentleness and bashfulness.    He overcame this bashfulness enough to finally tell Caroline Davis about his great love for her.  He told her how he had worshipped her since a little boy at Wesleyan Academy.  How he followed her to Cornell and back to Philadelphia; how he had seen her preference for big, strong heroic boys and how he was determined to become the best of these qualities.  He asked her if some day she would marry him.  Caroline declined Win’s advances and expressed no pride or interest in having won the love of such a national hero.  Win Osgood was crushed.  

With his romantic dreams in shambles, he became somewhat depressed and restless. He was the head coach of the 1895 Indiana football team, where he had an unfulfilling 4-3-1 record.  He also played for the semi-professional 1895 Indianapolis Light Artillery Football team; joining midway through the season as a player/coach with decisive victories against Notre Dame and Butler.  Soon after the season, he confided to a friend. “I can’t stand this sort of existence any longer, I want to go where there is fighting.  I need the excitement and the danger to make me forget.” He became excited by the news of the struggle for liberty in Cuba and wanted to join one of the expeditions being assembled in the US to aid the revolutionists.  Win sought the advice of his father, Captain Osgood.  His father pointed out the dangers and Win articulated the worthiness of the cause.  Win felt a moral obligation and duty to offer his assistance to these repressed people.  

His proffered services as a volunteer were gratefully accepted by the leaders of the insurgents, to whom his knowledge and ability as a civil engineer, no less than his personal bravery and inborn capacity for leadership, soon rendered him of great value.  Win Osgood was commissioned as a Commandant in the Cuban army on April 11, 1896.  While waiting for his expedition to start, Osgood passed the time in cross-country running and other athletic exercises.  His marksmanship was also an object of much attention, as was the use of the sword.  He reached the shores of Cuba in the summer of 1896, where he immediately rose to the rank of Major in the artillery under General Calixto Garcia. 

Win Dana Osgood, circa 1893

On October 18, 1896 the Cuban General Garcia and General Maximo Gomez joined forces and moved upon a small shoreline village called Guaimaro, which was strongly fortified and defended by the Spaniards. After much hard fighting and a brilliant charge led by Colonel Mario García Menocal, the largest fortification was taken. During the battle, Major Osgood was in charge of shelling several blockhouses with a Hotchkiss cannon using 12-pound shells. Osgood's artillery unit was under steady fire from small arms. When Osgood stooped over the gun to adjust the sight to account for the wind, he made the remark, “think that will do.” At that moment, he was hit through the skull by a Mauser bullet fired by a sharp-shooter stationed in the church tower eleven hundred yards away. Osgood was carried from the location by his comrades and hurried down the hill to the aid station. Without re-sighting the artillery piece, Osgood’s second in command Major Frederick Funston gave the order to fire the gun and the shell hit one of the blockhouses.  He died four hours later and was buried under a mango tree in an unmarked grave.  

Accolades from across the country poured in upon news of Winchester Osgood’s tragic demise.  His University of Pennsylvania roommate and fraternity brother, George Orton stated at his memorial:  Do not think of him buried in Cuban soil or laying in some marshy grave.  Such thoughts are sacrilege.  That Apollo form, those muscles fit to vie with those of Hercules, that kindly beaming face and graceful carriage may indeed have gone way.  But let us remember him as we all have seen him; flashing down the field for a touchdown or tackling as none other could; crossing the line a winner in the bicycle race, or a victor with the gloves or wrestling bout.  Or again let him be remembered as the perfect gentleman, pure in word and deed, faithful to friends, gallant to ladies and courteous to all.  For “Who’s good, He’s good…Osgood.”

Reference:  Wikipedia and several Phi Gamma Delta Journals. 

My deepest appreciation to Linda Mesinar for all her help and encouragement over the last ten years.  This site wouldn't be possible without her!

The Cuban Hero music sheet 1897

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