Philadelphia, Pennsylvania got its first NHL team in the 1930–31 season. The Pittsburgh Pirates, in this context a previously-successful hockey team, moved across the Allegheny Mountains at the instigation of owner Benny Leonard, the legendary lightweight boxing champion who was a Jewish kid from New York but had fought many of his most famous bouts in the City of Brotherly Love. Granted, the Pittsburgh Pirates in their last season had been a terrible hockey team, with a record of 5-36-3, nine wins below the next-worst team in the NHL, but they had picked up 19-year-old future Hockey Hall of Famer Syd Howe, useful young forward Wally Kilrea, and heavyweight defenseman Allan "Big Pete" Shields from Ottawa in the offseason, so in Philadelphia the newly-christened Quakers were hardly going to be worse.
With their tiger-stripe sleeves and attractive cursive chest logo, the Quakers actually seem to have looked rather sharp. Everything was black and white in the 1930s so maybe they were ghastly in person but the surviving photos show a timeless quality that could walk into a Heritage Classic and sell 20,000 sweaters today. They had a few neat players: besides Howe, a young, tough little forward named Gerry Lowrey could chip in points, Kilrea wasn't in Howe's class but went on to 316 NHL games in an era where that meant something, Shields and Johnny McKinnon gave established defense, skipper Hib Milks wasn't bad, and rookie starting goalie Wilf Cude was only 20 when the season started but became solid with the pre-war Canadiens. And Philadelphia was a hockey city: their Can-Am team, the Philadelphia Arrows, drew 4,000 or so fans a night to the Philadelphia Arena.
This is all a rather feeble look at the bright side, for the Philadelphia Quakers were in fact completely doomed. Benny Leonard was only the official owner; the real man was bootlegger "Big Bill" Dwyer, who besides his unsavory reputation was also the owner of the New York Americans and therefore could not be officially involved with the Quakers. They had no stars and their few NHL-level talents were either too old or too young. Off the ice, the Philadelphia Arena was a 5,000-seat barn unsuitable for major league hockey in a declining neighbourhood. Pittsburgh was being ravaged by the Great Depression, but Philadelphia was even worse. The harder the Quakers organization tried, the more pathetic things became, and they did not try for long. In the end they suffered the perhaps-unique distinction of being an NHL team outdrawn by a minor hockey team in the same building.
And somehow they did get worse. The 5-36-3 1929–30 Pittsburgh Pirates became the 4-36-4 Philadelphia Quakers. By points percentage it is the worst two-year run in NHL history, yes, worse than the expansion Washington Capitals. In the end the Quakers couldn't even fold properly. Frankly it's a miracle hockey survived in Pennsylvania at all.