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straddled the line between genius and madness throughout
his career, often leaning from one side to the other. It makes him
a difficult figure to define from a historical standpoint, whether
one sees him as an all-time great, as an all-time what-if or as
someone who falls in the vast chasm that exists between those two
extremes. The brilliance of Penn’s prime has been overshadowed by
the fact that he fell off a competitive cliff, suffering a record
seven consecutive defeats before being released by the
Ultimate Fighting Championship

As Penn now attempts to navigate the legal issues that continue to
hound him and reflects on what he accomplished inside the cage, a
look at a few of the rivalries that helped him carve out a

What was supposed to be a coronation for Penn turned into
affirmation for Pulver, as “Lil’ Evil” retained his lightweight
championship with a majority decision over the favored Hawaiian in
the UFC 35 main event on Jan. 11, 2002 at the Mohegan Sun Arena in
Uncasville, Connecticut. Judges Douglas Crosby and Tony Mullinax
cast 48-45 and 48-47 scorecards for Pulver, while Jeff Mullen
scored it a 47-47 draw. Penn had won his first three fights under
the UFC banner—Joey
, Din Thomas and
Caol Uno
were the victims—in less than eight minutes combined and appeared
to have the upper hand against the champion early on, nearly
submitting him with an armbar at the end of the second round.
However, Pulver’s indomitable will slowly took over, as he held his
own with Penn in both the standup and grappling exchanges in the
later rounds. While the decision remains somewhat controversial to
this day, no one can discount Pulver’s efforts in what became his
signature victory. By the time they met for a second time, Pulver
was a shell of his former self and lacked the wherewithal to deal
with the Hawaiian’s otherworldly skills. Penn submitted the
protégé with a second-round rear-naked choke at “The
Ultimate Fighter 5” Finale on June 23, 2007. It was Pulver’s final
appearance inside the Octagon.

Hughes had a runaway-train feel about him when he risked the
welterweight crown against Penn in the UFC 46 co-headliner on Jan.
31, 2004 at the Mandalay Bay Events Center in Las Vegas. One
opponent after another had yielded to his toxic blend of power
wrestling, ferocious ground-and-pound and technical grappling, as
he had rattled off five consecutive title defenses. Penn was one of
the most gifted fighters the sport had ever seen and had rebounded
from a majority decision loss to the aforementioned Pulver, his
victories over Paul
, Matt Serra and
sandwiched around a five-round draw with Caol Uno. Most
seasoned observers believed Hughes was too strong for the popular
but undersized Hawaiian. They could not have been more wrong. Penn
took it to the champion on the feet, and when Hughes stumbled after
whiffing on a left hand, “The Prodigy” dumped him to the mat. Penn
passed guard, advanced to the back and cinched a rear-naked choke.
Hughes had no choice but to tap with 22 seconds left in the first
round, as he emerged from the choke with a blank stare and
reluctantly passed the torch. Penn made it look easy. They met
twice more in the ensuing years. Hughes exacted a measure of
revenge with a second-round technical knockout at UFC 63 in 2006
before Penn closed the book on their trilogy with a 21-second
knockout in 2010.

Penn tied up some loose ends and retained the undisputed
lightweight championship in the UFC 84 headliner, as he wiped out
Sherk—“The Muscle Shark” had been stripped of the title less than a
year earlier due to a positive test for performance enhancers—with
a third-round knee strike and follow-up punches on May 24, 2008 at
the MGM Grand Garden Arena in Las Vegas. The Hawaiian controlled
the majority of the match with a punishing jab, keeping Sherk at
bay while denying both of his attempted takedowns. The damage
started to pile up in the third round, with Sherk bleeding from
cuts near both eyes. In the waning seconds, Penn charged at the
Greg Nelson protégé and blasted him with a flying knee that sent
him careening into the fence. A semi-conscious but defenseless
Sherk was then met with rapid-fire punches until the horn sounded.
Penn declared he was done, and referee Mario Yamasaki agreed. “The
Prodigy” connected on 69 percent of his significant strikes in the
15-minute affair, outlanding Sherk by a 122-46 margin.

A man who had been urged by many to drop to 145 pounds ended the
reign of the sport’s most dominant lightweight, as Edgar used his
speed, movement and a pair of takedowns to outpoint Penn in the UFC
112 co-main event on April 10, 2010 at the Ferrari World Concert
Arena in Abu Dhabi, United Arab Emirates. Scores were 50-45, 48-47
and 49-46, all in Edgar’s favor, as he laid claim to the undisputed
lightweight crown. Bearing bruises under both eyes, Penn seemed
resigned to defeat as he awaited the decision from the judges. He
had not lost as a lightweight in more than eight years. Edgar
grounded the Hawaiian with authority and punctuated his stunning
triumph with a strong fifth round. There, he consistently beat the
champion to the punch and stayed out of danger. Edgar utilized
feints and a multipronged standup attack throughout the competitive
five-round encounter. Penn landed the more powerful punches but
never seemed to shake the resolve of the challenger, who appeared
unfazed by the pound-for-pound great’s considerable aura. Penn
again relied heavily on his stiff left jab and flurried late, but
he seemed to slow noticeably after chasing “The Answer” for the
full 25 minutes. Edgar won both rematches against “The Prodigy,”
leaving no doubt as to who was the superior mixed martial artist.
He took a unanimous decision from Penn at UFC 118 a little more
than four months later, then buried him with third-round punches at
“The Ultimate Fighter 19” Finale in 2014. Advertisement