Ok, "pudge" means fat, and a "heffelfinger" is a sex act, so..surely this was a made-up name, from a humorous story or satire.
But no, there really is a Heffelfinger family, with a member named Pudge.
Obviously I have to write a post about him. Someone with such a distinctive name must have some gay connection.
I couldn't find any shirtless pics, but he fills out this Yale sweater well. He was 6'3 and 200 lbs, a giant in his era.
Later he coached the California Golden Bears, the Lehigh Brown and White, and the Minnesota Golden Gophers, plus returning to Yale as a guest player and coach. He appeared in exhibition games through his life -- the last time he played was in 1930, when he was 63).
Meanwhile, he published sales booklets for sports equipment and an annual book, Pudge Hefferfinger's Football Facts.
He produced a sports quiz radio program, plus a spy show, Secret Agent K-7.
For a career, Pudge worked in the shoe business and real estate, and spent twenty years as the Hennepin County, Minnesota Commissioner. In 1930 he ran unsuccessfully for Congress.
He died in Blessing, Texas in 1954, leaving a wife and four children.
The moustached guy with feminine hand thing and his wrist an inch or so from Pudge's crotch is Bum McClung, aka Thomas Lee McClung (1870-1914), three years younger, a "frosh" who became a football star in his own right, and, like Pudge, returned to Yale to coach throughout his life.
After graduation, Bum became the treasurer of Yale University, and in 1909 the United States Treasurer under President Taft.
When he died unexpectedly from an illness in 1914, an obituary called him "a remarkable athlete, a wonderful football player, a lovable classmate, a diligent student, a manly man–a type Yale men idealize for emulation."
You'd never make it to a high office in the U.S. today without being married, but Bum managed.
The late 19th century was the "era of the bachelor," when many men who liked women feared the loss of freedom that came with marriage, as well as the debilitating effect of the sex act itself. Being unmarried doesn't necessarily mean that Bum was gay.
Maybe he and Pudge....
Here's another picture of Bum McClung with an unidentified friend. He's doing that feminine hand thing again.