Sports Showdowns That Never Were

By Kevin Cook

If the Pacquiao-Mayweather fight never happens, it’ll join this list of great woulda-shouldas.

In the November issue of Playboy, writer Kevin Cook journeyed to the Philippines to profile boxer, politician, activist and hometown hero Manny Pacquiao, who has a Nov. 12 welterweight title bout against Mexico’s Juan Manuel Marquez. Boxing fans across the globe are hoping it will be Pacquiao’s tune-up to an eventual showdown against Floyd Mayweather. Cook doesn’t mince words about Mayweather ducking Pacquiao for the last two years. Should the two eventually meet in the ring, it would be an epic moment for the sport. But if it falls through, it will be just another monumental sports showdown that never came to pass. Here’s Cook’s list of great coulda, woulda, shoulda moments in sports history:

1965 Green Bay Packers vs. Buffalo Bills

In the year before Super Bowl I, coach Lou “Nick’s cousin” Saban’s Bills rolled to a 10-3-1 record behind QB Jack Kemp. Buffalo blanked the Chargers 23-0 in the AFL title game with help from three field goals by Pete Gogolak, the first soccer-style kicker. Meanwhile Vince Lombardi’s Packers, also 10-3-1, topped Jim Brown and the Browns for the NFL crown. Could the Bills have won their only Super Bowl if the Super Bowl era started a year earlier?

What woulda happened

Packers linebacker Ray Nitschke gives Kemp existential angst and a concussion, Kemp’s backup Daryle Lamonica fires a pair of pick-sixes and Green Bay prevails, 20-10. Pee-Wee leaguer Scott Norwood, 5, watching on TV, says, “I don’t feel good about this.” 

1932 New York Yankees vs. Negro League All-Stars

With Babe Ruth hitting .341 with 41 homers and Lou Gehrig batting .349 with 151 RBIs, the mighty Yanks won 107 times in a 154-game season. They swept the Cubs in the World Series, Ruth swatting his famous “called shot” in Game 3. But the Babe’s shot was off Charlie Root, not Satchel Paige, whose batterymate Josh Gibson and bullet-fast centerfielder Cool Papa Bell made the Negro League All-Stars even better up the middle than the Yanks.

What woulda happened A Gibson grand slam off Lefty Gomez ties it in the ninth. Starting pitcher Paige hangs in until the 15th, when Martin Dihigo’s bunt single gives the Stars their first lead. In the bottom of the inning, with two on and two away, Ruth launches a shot over the right-field fence. Bell races through the stands to the parking lot, jumps a fence and hauls the ball in 500 feet from the plate to preserve Paige’s 5-4 victory.

John L. Sullivan vs. Fight Club Brad Pitt

The mustachioed Sullivan ruled the ring in the late 1800s, the last days of bare-knuckle prizefights. A century later, Tyler Durden ruled the basement brawls of Chuck Palahniuk’s novel and David Fincher’s film, starring Pitt. Both fighters were 5’11” but Sullivan weighed 212 to Pitt’s 160.

What woulda happened The first rule of bare-knuckle boxing is, Owww! Pitt lands the first flurry, breaking his hands on Sullivan’s jaw. The champ advances relentlessly, smashing Pitt’s nose and teeth while Pitt laughs maniacally. In the 40th round Sullivan, briefly distracted by a screaming, scratching Helena Bonham Carter, ends the fight and Pitt’s life.

Michael Jordan vs. LeBron James

When Scottie Pippen suggested during the playoffs that LeBron might be better than Michael, fans pictured a one-on-one battle: the 6’6” Jordan in his prime, stealing the ball from 6’8” LeBron for a tongue-lolling tomahawk jam while King James was still looking for his talcum powder. But would it be that easy?

What woulda happened James grabs enough offensive boards to stay close. With 00:10 on the clock, LeBron trails by a point. Five seconds…three, two…what will he do? Nothing—he’s still hoping to dish off to Dwyane Wade.

Diamond Jim Brady vs. Mr. Creosote vs. Joey Chestnut

Before competitive eating became a “sport,” 19th century tycoon Brady’s typical meal featured turtle soup, bread, three dozen oysters, six crabs, six lobsters, two whole ducks and a sirloin steak. Creosote, a bloated glutton in Monty Python’s 1983 The Meaning of Life, ate more than that before exploding. Eating champ Chestnut’s current record is 66 hot dogs and buns in 12 minutes.

What woulda happened

With Creosote DQ’d for vomiting, Chestnut finds that you can’t soften up a sirloin by dunking it in water. Diamond Jim celebrates his win with an Oreo CheeseQuake Blizzard.

2003 Cubs-Yankees World Series

What if Cubs fan Steve Bartman hadn’t interfered with Cubs outfielder Moises Alou in the 2003 NLCS? The star-crossed Chicagoans, led by pre-injury phenoms Kerry Wood and Mark Prior plus neckless corked-bat-swinger Sammy Sosa, coulda gone to the Series against a 101-61 Yanks club starring neckless Roger Clemens and Jason Giambi.

What woulda happened

Trailing 3-2 in Game 7, the Cubs load the bases against Mariano Rivera with nobody out in the ninth. After a weird, brief delay when a billy goat wanders onto the field, Alou lines into a 5-4-3 triple play.

Pacquiao vs. Mayweather

The fight that oughtta happen—the sport’s premier technician against Pacquiao’s superior power and speed. The early rounds would prove that Pacquiao can’t outpoint the unbeaten Mayweather. To win, he’ll have to knock him out.

What woulda happened

Mayweather leads on all cards going into the 12th, when Pac-Man connects with a lightning left that drops Floyd to 42-1.


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