5 underdogs who flopped after their biggest win

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Danny Howard

November 3rd, 2020

Nothing shocks the sports world like an underdog. Upsets usually signal the arrival of a new star or a changing of the guard, but not all fighters can build on that momentum. These five fighters won big only to flounder shortly after.

5. Darryl Pinckney

When a former world champion is facing a fighter with an 18-18-2 record, it has "bathroom break" written all over it. However, Pinckney scored a shocking one-punch KO of Junior Jones that proved anything can happen in a boxing ring. While this could’ve been then moment when Pinckney transitioned from a doorstop to a legitimate contender, it ended up just being a lucky punch and Pinckney went back to his losing ways in short order.

4. Kirkland Laing

While Roberto Duran was trying to move away from the infamous "No Mas" fight and recovering from a dominant loss to Wilfred Benitez, Duran suffered the most embarrassing defeat of his career at the hands of the unheralded Kirkland Laing. One would imagine that defeating a member of the fabled "Four Kings" would change Laing’s fortunes, but instead he retreated back to the UK and remained a regional talent.

3. Leon Spinks

It’s one thing to beat the greatest fighter that ever lived, but it’s another thing to do so in only your eighth fight. That was the story of Leon Spinks, who hustled an out of shape and aged Muhammad Ali to win the belt in 1978.

Unfortunately for Spinks, it wasn't all sunshine and rainbows after the massive upset, especially after Ali easily beat him in a rematch. Substance abuse problems and poor performances took Spinks from heavyweight glory to a miserable 26-17-3 record to end his career.

2. Jeff Horn

Nobody wanted to see Manny Pacquiao fight some guy named Jeff Horn, but when Pacquiao did and Horn won a controversial decision, Horn suddenly became a made man in the sport. Knocking off a legend and winning a title is one thing, but sustaining that momentum is clearly another.

Horn got a chance to prove he was more than a bad decision as champ, but got hideously beaten by Terence Crawford and then later split a two-fight series with Australian journeyman Michael Zerafa. Most recently, Horn affirmed his status as a middling fighter after getting trounced by Tim Tszyu in his third defeat by stoppage.

1. Buster Douglas

We all know the story of Buster Douglas, who overcame 42-to-1 odds to beat Mike Tyson and win the heavyweight title. The victory instantly made Douglas a legend and should have set him up for an incredible run for the title, but we were soon to find out that Douglas wasn’t ready for the responsibilities of being champion.

Spurning a Tyson rematch to instead collect a $25 million payday against Evander Holyfield, a fat and flabby Douglas was stopped in three rounds and retired following the bout. A minor comeback followed in the late 1990s, but Douglas never came in sniffing distance of meeting the expectations following the Tyson win.