B.J. Penn (Dave Mandel/Sherdog)

The Rise and Fall of B.J. Penn: An Illustrated Look at Penn’s Best and Worst

Despite a lackluster record of 16-11-2 without a win since 2010, B.J. Penn is still regarded as the greatest lightweight of all time. He revolutionized the sport. You could even call him the father of modern mixed martial arts. With a highly accomplished Brazilian Jiu-Jitsu background and the boxing to compete with anyone on the feet, Penn was truly the first well-rounded MMA fighter. In an era of linear stars like Matt Hughes and Chuck Liddell, Penn broke the mold and became the first person to be adept in all areas of MMA. He redefined the use of the jab in MMA, and his guard passing is still heralded to this day. Say what you want about his motivation and decision making, but the sport would not be what it is today if it wasn’t for Penn.


Penn’s jiu-jistu roots led him to Ralph Gracie when Penn was just 17. He earned his purple belt with Gracie, but then traveled to the famed Nova União camp to train under another grappling legend, Andre Pederneiras. Penn was awarded his black belt by the coach and went on to become the first non-Brazilian to win the World Jiu Jitsu Championship after only three years of training under his belt. Thus, “The Prodigy” was born.

Penn has always been known for his dangerous and versatile guard, but it did not show up much in his MMA career. It was his miraculous technical top game that became a thing of legend. When on top, Penn looks to get half guard or half butterfly guard to work his way to mount. When on bottom in full guard, a fighter’s first reaction is to get into butterfly guard, elevate their opponent’s hips and slide out. Penn uses this tendency to trap one leg and elevate over the butterfly and move his way into mount. This is also called a leg weave or dope mount.


Penn also frequently uses a position still rarely found in MMA today called the chair sit. There are many different ways to use the chair sit, but he mainly uses it toget into mount.

Here, Penn chair sits from half guard, locking down his opponent’s right leg while leaving his right leg free to swing over into mount.

Again, Penn locks down his opponent’s right leg with a chair sit and uses his free leg to take Caol Uno’s back.

Chair sitting from half guard takes away an opponent’s ability to knee shield, shrimp or butterfly into their full guard. Demian Maia also uses a variation of this chair-sitting strategy to pass his opponent’s guard, but that is for another day. Penn’s offensive jiu-jitsu tactics changed the sport. Now, 15 years later, we are seeing some of his strategies being implemented in the UFC.


Early in his career, Penn was a counter-left-hook-happy striker who stood square and only used his hands to set up a takedown. Then, in his return to the UFC in 2006 against Georges St-Pierre, Penn developed a quick, snapping jab, along with a more bladed stance and a nasty counter right straight. In his fight with GSP, Penn focused on using the jab as a counter as St-Pierre was coming in. He controlled the first round with pretty much only the jab and almost won the fight.

After this fight, GSP went on to make a career off the exact jab Penn used on him.

Penn was masterful with this counter jab. Shortly after the first GSP fight, it seemed everybody was taking a page out of his book and using a similar jab. In boxing, the counter jab is a basic technique to stop an opponent in their tracks when coming forward. It was widely used by legendary boxers like Mike Tyson and Joe Louis.

Penn also used this counter jab to draw a counter from his opponent, which in turn can also be countered. In short, he’s throwing a jab to counter the opponent’s forward movement, which will draw a counter punch by the opponent that he can time, step back and counter over.

Here is legendary lightweight boxer Roberto Duran using this same tactic on Davey Moore. Roberto Duran was one of the most feared body punchers in his era, and this shows exactly why.

In one of his jiu-jitsu technique DVDs — yes, that used to be a thing; Google it — Penn described his style as “taking the basics and ramming it down my opponent’s throat.” Although his jiu-jitsu style uses some very unique techniques, his boxing was exactly that — taking the basics and perfecting them. His bladed stance allowed his newfound jab to be even longer while making his head and target area further from his opponent. This bladed stance allowed him to advance or retreat as fast as possible when needed, and to more efficiently land the counter right he fell in love with later in his career.

As much as this new style of boxing helped Penn to become the greatest lightweight of all time, it equally caused his rapid decline. When standing side on in a bladed stance like he does, his lead leg is open to leg kicks. Penn also stands heavy on the lead leg, which makes it much harder to check kicks, something he was never good at doing. The bladed stance also makes pivoting on the lead foot to face the opponent much slower, which allows opponents with frequent lateral movement to circle around him, making him follow them and leaving Penn one step behind. Frankie Edgar was his first opponent to recognize this, and he dominated Penn in all three fights with this strategy.

Edgar circles, leaving Penn trailing behind and open to strikes off the pivot.

Notice how long it takes for Penn to turn and face Edgar while Edgar steps to his left and double jabs.

The Decline of a Legend

After Penn’s back-to-back losses to Edgar, it was clear that a new era had begun. Although Penn is the originator of how the game is done today, his footwork did not evolve with the sport and was the main cause of his decline. After knocking out a 36-year-old Matt Hughes a few months after the second loss to Edgar, Penn has since gone 0-4-1 and was dominated in all four losses. Two of those fights were at 170 pounds, where he went up against Nick Diaz and Rory MacDonald. Diaz and MacDonald executed the same game plan and found another hole in Penn’s striking. With Penn not having the footwork to deal with a laterally moving fighter like Edgar, he also did not have the footwork to stop himself from getting backed down to the cage. Diaz was the first to exploit this, and MacDonald followed a year later.

Diaz intelligently picked his strikes to keep Penn against the cage, and he easily cuts Penn off when Penn tries to circle out.

MacDonald mixes up kicks and punches to the head and body, while never getting too aggressive and allowing Penn to circle out.

Both men even did their fair share of taunting.

Despite being the champion early in his career and taking GSP to a hard-fought split decision, Penn was never a good fit for the welterweight division. He was massively undersized and no longer had the reach or grappling advantage he had at lightweight due to his opponent’s size. Out of his 29 professional fights, only 16 were at lightweight, a division where he only lost three times. Two of those defeats were to Edgar, who would go on to be arguably the second-best lightweight of all time. If it wasn’t for Penn’s odd decision-making, which took him from fighting anywhere between 145 pounds all the way to 205 pounds against Lyoto Machida, he could have been one of the most dominant fighters of all time.

It wasn’t until halfway through his career in 2007 when Penn decided to stick to lightweight for a while. He beat Joe Stevenson for the vacant title and went on a five-fight winning streak while finishing every opponent as champion and solidifying his spot as the greatest lightweight ever. If Penn would have remained at lightweight, then we might have been putting him in the discussion for greatest of all time. However, his decision to fight at four different weight classes and go 4-8 outside of lightweight tarnished what could have been.

Penn’s boxing and jiu-jitsu revolutionized the sport, and his legacy will never be forgotten. He is one of three fighters to hold belts in two different divisions. He popularized the jab in MMA and was the first well-rounded MMA fighter. He is regarded as the greatest lightweight and guard passer in MMA history. His flexibility and jiu-jitsu tactics are still rarely found today. It just goes to show how unique of a fighter Penn was in his prime.

Penn fights again this Sunday at UFC Fight Night 112 against journeyman Dennis Siver. It’s a fight that actually makes sense for him. Perhaps he will even go out with a bang and end his storied career with one last win.