Motor City sports great, Gordie Howe, Mr. Hockey himself, brushed shoulders with Detroit’s infamous Purple Gang in the prime of his Hall of Fame NHL career. Howe and his soon-to-be-crowned Stanley Cup champion Detroit Red Wings played the first outdoor game on record in pro hockey history in the winter of 1954, an exhibition contest held in Michigan’s Upper Peninsula against a rag-tag prison squad with members of the murderous Purple Gang on it.

The NHL’s all-time leader in games and seasons played, Howe died of natural causes at the age of 88 late last week. The Purple Gang was a Jewish mob which ruled Detroit’s Prohibition Era underworld landscape and was tied to an estimated 500 slayings during its’ reign that lasted less than a decade (1925-1933).

On February 2, 1954, at the request of incarcerated Purple Gang chieftains Ray Burnstein and Harry Keywell, Howe and his Red Wings teammates traveled to Marquette State Prison for a friendly showdown on the ice versus the penitentiary’s inmates. It got out of hand fast.

Author Daniel Waugh’s excellent Purple Gang book, Off Color, discusses the game. (Purchase Waugh’s book here).

The Red Wings went ahead 18-0 after one period and then switched up the squads with Howe and future Hall of Fame goalie Terry Sawchuk joining the prison team for the remainder of the event. Months later the Red Wings won the first of two straight Stanley Cup Trophies, Howe’s third and fourth championship ring, respectively. At the time of the exhibition, Howe was in the midst of reeling off five NHL scoring titles in a row.

Burnstein and Keywell were at Marquette State Prison on a murder rap – they were convicted of leading the four-person hit team that carried out the notorious 1931 Collingwood Manor Massacre, a bloodletting of a subunit of the Purple Gang known as the Little Jewish Navy responsible for transporting the gang’s booze across the Detroit River from Canada and into the more than 50 Purples-controlled bling pigs and speakeasies tucked away all across the city. Keywell was one of the shooters who gunned down the three Little Jewish Navy bosses (Harold “Hymie” Paul, Isadore “Izzy the Rat” Sutker and Joseph “Nigger Joe” Lebovitz), Burnstein, in charge of the Purple Gang’s enforcement wing, was the man tasked with planning the slaughter.

The Purple Gang was founded by Burnstein and his three brothers (Abe, Joe and Izzy) on Detroit’s east side in the early 1920s. Keywell and his brother Phil were two of the Burnsteins’ closest friends and top lieutenants. They were all giant sports fans and hobnobbed around town with a number of pro athletes, owners and coaches.

According to Detroit Police Department records, the Burnsteins became acquainted with legendary NHL head coach Jack Adams when he arrived in Michigan in 1927 to help jumpstart a new franchise called the Detroit Cougars, eventually rechristened the Detroit Red Wings five years later. Adams was at the helm for more than three and a half decades and turned the franchise into multiple-time world champions.

In the summer of 1953, Adams and Red Wings all-star forward Ted Lindsay were on a Stroh’s Brewery-sponsored promotional tour throughout the state concluding with a stop at Marquette State Prison in the UP where Adams ran into Ray Burnstein, his old drinking buddy from his bootlegging days. Burnstein had requested that the prison’s warden Emery Jacques bring Adams by his cell after Adams, an NHL Hall of Famer as a player, coach and general manager, and Lindsay, the left wing alongside Howe at center on what became known affectionately as the “Production Line,” held a demonstration in the prison mess hall at which point Burnstein asked if they’d return in the winter for an exhibition.

Surprisingly, they agreed. The Red Wings franchise even donated the equipment for the game and provided the money to have a custom-designed ice rink constructed in the prison’s expansive yard. The inmate team wore uniforms that read “Emery’s Boys” in honor of the warden, however, called itself the “Prison Yard Pirates.” The team was coached by prison athletic director, Leonard (Oakie) Brumm, a member of the University of Michigan’s National Championship hockey club in 1948 and former college coach at the University of Alaska-Anchorage.

Getting pro athletes to come play sports with them and their pals in prison wasn’t a new thing for Burnstein and Keywell. Back in 1941, Detroit Tigers slugger and future MLB Hall of Famer Hank Greenberg, another high-profile Purple Gang associate, accepted an invitation from Burnstein and Keywell to come participate in a prison baseball game.

Ray Burnstein was paroled in 1964 following 31 years behind bars and died in 1966. Keywell had been released the year prior and lived quietly in retirement from his underworld days in Metro Detroit until he passed away in 1997.

Howe finally hung up his skates and hockey stick in 1980, already into his 50s (52). He was a 23-time NHL All-Star selection and scored a career 801 goals (currently second all-time, best ever before Wayne Gretzky surpassed him).

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