Three-times World Champion, cultural icon, civil rights activist - Muhammad Ali was all these things and more. To many people he's simply "The Greatest", perhaps the most important athlete of the 20th century. Here's our list of the most expensive items of Muhammad Ali memorabilia ever sold.

25) Ken Norton III fight-worn trunks

(Image: Heritage Auctions)

Ali fought Ken Norton three times during his career. The first ended with victory for Norton, and a broken jaw for Ali. The second finished with Ali winning on points. And the third remains one of the most disputed decisions in boxing history.

Norton gave Ali a pounding at Yankee Stadium on September 28, 1976, and the fight went the distance. Unofficial scorecards had Norton ahead, and the fight commentator announced he would be "very surprised" if Norton has not won. He was then very surprised, as the referee's and judges' scorecards gave Ali the victory based on the final round.

The crowd booed, and Ali quickly announced he was retiring from boxing to practise his faith. That retirement didn't last long, and he was back in the ring the following year, but for many that third Norton fight marked the beginning of the end for Ali.

His trunks worn during the fight sold at Heritage Auctions in September 2016 for $43,020.

24) George Chuvalo fight gloves

(Image: Heritage Auctions)

In March 1966 Ali refused the military draft for the Vietnam War, and was quickly stripped of his boxing license in every U.S state due to his unpatriotic stance. So like many of his fellow conscientious objectors he headed north to Canada, to fight George Chuvalo, owner of one of the greatest chins in boxing history.

Canadian heavyweight Chuvalo was never knocked down during his entire boxing career, and just two fighters - Joe Frazier and George Foreman – ever stopped him with technical knockouts. He went the full distance twice with against Ali, losing both on points by wide margins, but after the first bout Ali described him as "the toughest guy I ever fought".

This pair of Ali's gloves from that fight, dated March 29, 1969, sold at Heritage Auctions in September 2016 for $47,800.

23) National A.A.U championship fight gloves

(Image: Leland's Auctions)

This pair of gloves was worn by the 18-year-old Cassius Clay on April 9, 1960, as he successfully defended his National A.A.U. title against Jeff Davis with a knockout in the second round.

He presented the gloves, along with his trophy, to his trainer Joe Martin, who had discovered Clay as a teenager in Louisville, Kentucky and moulded him into a champion fighter at his Columbia Street Gym. As the earliest pair of documented Ali fight-worn gloves ever offered at auction, they sold at Leland's Auctions in 2007 for $48,024.

22) Ken Norton III fight-worn boots

(Image: Heritage Auctions)

The third Ali-Norton fight proved a significant moment in the careers of both boxers.

Following his controversial points victory, Ali later stated in an interview: "I honestly thought he beat me in Yankee Stadium, but the judges gave it to me, and I’m grateful to them."

Having retired from boxing after the match, he made his comeback in 1977, but many observers – including his longtime doctor Ferdie Pacheco – believed he should have stayed out of the ring.

Norton said simply "I won at least nine or ten rounds. I was robbed." In years to come, he would describe the bout as the fight that broke his heart, and the last for which he was truly motivated.

Although he was retroactively granted the WBC title in 1978, following a defeat of Jimmy Young which effectively split the championship, he was never the same and retired altogether in 1981.

The boots worn by Ali in the fight at Yankee Stadium sold at Heritage Auctions in September 2016 for $50,190.

21) 1970s-era Passport

(Image: Heritage Auctions)

Ali was issued this passport by the American embassy in London on June 11, 1974, to replace one lost during his travels. It bears stamps which document Ali's trips to both Zaire and the Philippines, for two of the most famous fights in boxing history – The Rumble in the Jungle, in which he reclaimed his heavyweight title against George Foreman in October 1974; and the Thrilla in Manila, in which he fought Joe Frazier for the third and final time in October 1975.

Heritage Auctions sold the passport in April 2009 for $53,775, stating: "There is perhaps no other artifact from the life and times of Muhammad Ali that so effectively addresses his cultural importance as an official document issued by the country that had stripped him of his Heavyweight title, and that he used to go and reclaim it in Africa, and defend it in Asia."

20) Ken Norton fight robe

(Image: SCP Auctions)

Ali fought Ken Norton three times during his career, with both men winning on a split decisions before Ali controversially won the third bout.

The fight took place at Yankee Stadium in New York on September 28, 1976, and once again Ali won on points after both fighters entered the ring level by the final round. However, Ali had taken a beating from Norton, and to this day the fight is regarded as one of the disputed results in boxing history.

The robe in which Ali entered the ring that night was originally part of the collection of Drew 'Bundini' Brown, his long-time confidante and cornerman, and sold at SCP Auctions in December 2012 for $55,152.

19) Henry Cooper fight gloves

(Image: Fight Saga)

In June 1963 Ali, then still known as Cassius Clay, travelled to London to fight English heavyweight Henry Cooper at Wembley Stadium.

The fight is famous for Cooper's left hook known as "'Enry's 'Ammer", which felled Ali in the fourth round. His trainer Angelo Dundee illegally used smelling salts to revive Ali, and he went on to win the fight in a controversial victory. Ali later said Cooper "had hit him so hard that his ancestors in Africa felt it", and he even phoned Cooper on the 40th anniversary of the fight to reminisce about it.

The gloves Ali wore during the fight sold for £37,600 ($53,000) at Christie’s in 2001.

18) Jimmy Young fight robe

(Image: SCP Auctions)

In April 1976 Ali fought Philadelphia fighter Jimmy Young in Landover, Maryland, in defence of his World Heavyweight title. Seven years younger and 21 pounds lighter, Young went the full 15 rounds, but lost when the ageing Ali was controversially awarded victory by the judges.

Angelo Dundee described it as Ali's "worst fight", and New York Daily News reporter Dick Young wrote "[Ali won] by the grace of three hero worshipping fight officials. I believe many people, the voting officials among them, refuse to believe what they see when one of their super-heroes doesn't function as expected." Following the fight, many began calling for Ali to retire, although it would be another five years before he hung up his gloves for good.

The Everlast robe worn by Ali at the event was another items owned by Drew 'Bundini' Brown, and it sold at SCP Auctions in December 2013 for $60,667.

17) Jean Pierre Coopman fight robe

(Image: Leland's Auctions)

In February 1976 Ali travelled to Puerto Rico, to defend his world heavyweight title against the relatively obscure Belgian fighter Jean Pierre Coopman. In front of a packed house at the Roberto Clemente Coliseum in San Juan, Ali dominated the fight and easily won with a knockout in the fifth round, in what was later described as "a glorified sparring session".

Ali's custom-made white satin robe from the bout sold at Leland's Auctions in 2015 for $68,474.

16) ‘Three Times World Champion’ Ring

(Image: Heritage Auctions)

Ali lost his World Champion title to Leon Spinks in Las Vegas in February 1978, in a spectacular upset which saw the out-of-shape champion dethroned by the 1976 Montreal Olympics Light Heavyweight Gold Medalist.

The pair fought a rematch a few months later at the Louisiana Superdome in New Orleans. This time in far better shape, and with sharper tactics, Ali won in a unanimous decision in 15 rounds, becoming the first boxer to win the Heavyweight championship three times.

This ring, bearing three diamonds and the motto "The Greatest Heavyweight World Champion", was commissioned to celebrate the historic victory and presented to Ali following the fight. Described as "one of the most important Muhammad Ali artefacts ever placed upon the public auction block", the ring sold at Heritage Auctions in August 2011 for $59,750.

15) Leon Spinks title fight rematch robe

(Image: Heritage Auctions)

The World Title rematch with Leon Spinks in September 1978 was historic in two ways. Not only did it mark Ali's record-breaking third title victory, but it was also the last boxing match the champion ever won.

This white satin robe was worn by Ali during the milestone event, and was part of Drew 'Bundini' Brown's personal collection. Regarded as "one of the most significant Ali artefacts ever offered, from the last day of glory in one of American history's greatest sports tales", the robe sold at Heritage Auctions in February 2015 for $74,687.

14) Floyd Patterson second fight gloves

(Image: SCP Auctions)

In September 1972 Ali defended his heavyweight title against Floyd Patterson at Madison Square Garden, in a culmination of their feud which had begun back in 1965. It was Patterson's third attempt to win the title for a third time, but at 37 he was past his peak and Ali comfortably won with a stoppage in the seventh round. Although he never officially announced his retirement, the fight marked the last time Patterson ever stepped into the ring.

The gloves Ali wore during the fight, still bearing trainer Angelo Dundee's pre-fight prediction that Ali would win by a knockout in the fourth round, sold at Heritage Auctions in September 2016 for $89,625.

13) Rumble in the Jungle boots

(Image: Robert Edwards Auctions)

Having been stripped of his title for refusing the Vietnam War draft in 1967, Ali then spent the years trying to reclaim it. On October 30, 1974 he finally squared up against George Foreman in Zaire for The Rumble in the Jungle, a world title fight which has been described as "arguably the greatest sporting event of the 20th century".
Ali both out-fought and out-thought Foreman, winning with a knock-down in the eighth round. According to Foreman: "I thought he was just one more knockout victim until, about the seventh round, I hit him hard to the jaw and he held me and whispered in my ear: 'That all you got, George?' I realized that this ain't what I thought it was."
The boots Ali wore during the fight against Foreman sold for $100,725 at Robert Edwards Auctions in 2013.

12) 'Thriller in Manila' boots

(Image: Heritage Auctions)

In October 1975 Ali faced up against Joe Frazier for the third and final time, in what would be one of the most remarkable and punishing fights of Ali's career. The two men went fourteen rounds in the boiling heat of Southeast Asia, with Ali initially wilting under Frazier's relentless blows.

However, Ali fought back remarkably and by the end of the 14th round both of Frazier's eyes were swollen shut. His trainer Eddie Futch ended it, telling Frazier "No one will forget what you did here today."

After the fight Ali described it as the "closest thing to dying that I know of", and it was later revealed that he was also ready to throw in the towel himself before the 15th round began.

Ali's fight-worn Thrilla in Manila boots – each bearing the good luck mantra "Mo Speeed", as written by Drew 'Bundini' Brown prior to the fight – sold at Heritage Auctions in July 2013 for $119,500.

11) Life Magazine Conversion to Islam letter

(Image: Heritage Auctions)

When Cassius Clay converted to Islam in 1964, many didn't, or wouldn't, believe the news. Amongst the doubters were the publishers of Life Magazine, who were set to feature the newly crowned World heavyweight champ on their cover in March 1964.

They refused to acknowledge the story until they had confirmation from the man himself, so Clay (who was yet to change his name) sent them this letter, which starts "I believe in the religion of Islam..."

It was the first public affirmation of his newly-found beliefs, written at a major turning point in his life, and marked a significant moment in the history of the Civil Rights movement in America.

The handwritten letter sold at Heritage Auctions in September 2016 for $131,450.

10) Rumble in the Jungle trunks

(Image: Grey Flannel Auctions)

An estimated 60,000 people packed into the 20th of May Stadium to see the Rumble in the Jungle in person, with millions more watching around the world. Prior to the fight, fans had been treated to a three-day music concert featuring the likes of James brown, B.B King and Bill Withers, but now it was time for the main event.

Using tactics he called the "rope-a-dope", Ali absorbed punishment from the younger, stronger Foreman whilst shouting "They told me you could punch, George!" His victory was seen as a major cultural event, and remains one of most iconic moments of Ali's career.

The trunks Ali wore for during the fight sold at Heritage Auctions in September 2016 for $143,400

9) 'Thriller in Manila' trunks

(Image: Heritage Auctions)

The Thrilla in Manila remains one of the most brutal and exhausting fights in heavyweight boxing history, and following the fight these trunks were retained by Drew 'Bundini' Brown, who marked them "Ali - Frazier Fight, Trilla (sic) in Manila, Pres. F. Marcos, Manila, Philippines, Oct. 1, 1975."

When Brown passed away in 1987, his entire collection of boxing memorabilia (many pieces of which appear on this list) was left abandoned in a storage locker, and sold off at auction in 1988 for non-payment of fees. These trunks were later photo-matched by experts to the historic fight, and sold at Heritage Auctions in August 2012 for $155,350.

8) 'Rumble in the Jungle' fight robe

(Image: Taschen/Neil Leifer)

The Rumble in the Jungle was seen as a major statement, with two prominent African-American fighters returning like heroes to Africa. One poster for the event laid it out simply, with the headline "From slave ship to the Championship".

Instead of the usual satin, Ali entered the stadium symbolically wearing a robe featuring woven African patterns and beadwork, much of which had ironically been hand-made in Hammersmith, West London. Following the fight the robe was reportedly left behind in the changing room, before Ali insisted on returning to find it.

In October 1997 the robe sold at Christie's for $156,000.

7) 'Fight of the Century' trunks

(Image: SCP Auctions)

Ali's first fight against Joe Frazier took place at Madison Square Garden in New York in March 1971. Dubbed "The Fight of the Century", it was Ali's first bout in three years after being barred from the ring for refusing the Vietnam War draft.

Viewed as a battle between two polar ideals, the liberal anti-war movement versus the conservative pro-war establishment, the fight took on an important symbolism in the US. It ended with Ali's first defeat in his professional career, but would serve as the first chapter in Frazier and Ali's continuing rivalry.

In November 2011, the red trunks worn by Ali during the fight were sold at auction by SCP Auctions for $173,102, setting a then-world record for a piece of boxing memorabilia.

6) 'Rumble in the Jungle' title belt

(Image: Heritage Auctions)

Just two of Ali's WBC Title belts are known to have survived, with the first tucked away in a long-term private collection.

The second belt graced Ali's waist following the Rumble in the Jungle, perhaps the most culturally significant boxing match of all-time.

It later ended up in Drew 'Burundi' Brown's storage locker, which stood abandoned after his death in 1988, until the contents were auctioned off to cover unpaid fees. The majority of the items in Brown's collection have since sold again, but this heavyweight title belt remained off the market for more than 25 years.

Described as "the most significant boxing award ever made available at public auction", and "a truly priceless artefact of the American experience", the belt sold at Heritage Auctions in September 2016 for $358,500.

5) Military draft refusal letter

(Image: Heritage Auctions)

Having become the heavyweight world champion in February 1964, Cassius Clay converted to Islam and changed his name to Muhammad Ali a few months later.

He then became involved in the Civil Rights movement, and in 1966 refused the military draft for the Vietnam War on the grounds of his religious beliefs, claiming "Man, I ain't got no quarrel with them Viet Cong...Why should they ask me to put on a uniform and go ten thousand miles from home and drop bombs and bullets on brown people in Vietnam while so-called Negro people in Louisville are treated like dogs and denied simple human rights?"

He was arrested, systematically denied a boxing license in every state and stripped of both his passport and his world title. It would be four years before he was able to box again, although his principled stance helped elevate Ali from a champion athlete into an important cultural and political figure in his own right.

His 1966 letter requesting religious exemption from the military draft board sold at Heritage Auctions in February 2015 for $385,848.

4) ‘Fight of the Century’ gloves

(Image: Heritage Auctions)

After being stripped of his world title in 1966 for refusing the draft, it would be five years before Ali had the chance to win it back. The 'Fight of the Century' against Joe Frazier marked the first time two undefeated boxers had ever fought each other for the heavyweight title. And after 15 rounds, Frazier remained undefeated.

The gloves worn by Ali during his first professional loss, in one of most hyped and politicized boxing matches of all time, were described as "among the most important items of boxing memorabilia ever to be offered at auction." Offered from the collection of Ali's trainer Angelo Dundee, they first sold at SCP Auctions in December 2012 for $385,848, then again at Heritage Auctions in August 2014 for $388,375.

3) Sonny Liston first championship title fight gloves

(Image: Heritage Auctions)

Ali, then still Cassius Clay, got his first shot at the World Heavyweight title in 1964 against the frankly terrifying Sonny Liston, a convicted armed robber who learnt to fight in the Missouri State Penitentiary.

Nobody predicted a victory for Clay, with the Los Angeles Times writing "The only thing at which Clay can beat Liston is reading the dictionary." But Clay was full of confidence, and wound up his opponent at the weigh in, walking into the room with an African walking stick and a jacket which read "Bear Huntin'". "Tell Sonny I'm here. Bring that big ugly bear on!" yelled Clay. Liston emerged and charged at the challenger. "Someone is gonna die at ringside tonight!" screamed Liston, charging at his challenger as the event descended into chaos.

However, once inside the ring it became clear that Clay meant business. As the fight progressed, he used his speed to avoid Liston and land his own lightning-fast combinations. One ringside commentator screamed "This could be the upset of the century!", and soon it was Clay's turn to shout out loud "I'm the greatest! I shook up the world!" -  as Liston quit on his stool before the seventh round began.

The man who would soon become Muhammad Ali had won his first world title, and was on his way to immortality.

Having been described as "the most important boxing gloves that exist, relics not only of one of sport's great David and Goliath tales, but also instruments that changed the course of American history", the gloves sold at Heritage Auctions in February 2014 for $836,500.

2) Ali & Liston's 'Phantom Punch' gloves

(Image: Heritage Auctions)

After Ali defeated Liston in 1964 to claim his first world title, the pair met in a rematch in Maine for what remains one of the most controversial bouts in boxing history. It was the first time Muhammad Ali stepped in a boxing ring as 'Muhammad Ali', and anticipation was high following his stunning previous victory.

However, the crowd was stunned midway through the first round, when Ali threw what became known as the "Phantom Punch". Liston hit the canvas and was counted out, whilst Ali screamed for him to get back up and fight, but the fight was over in less than three minutes. To this day many believe the punch wasn't strong enough to knock Liston out, and that he took a dive due to everything from gambling debts to threats from the Mafia or the Nation of Islam.

Following the controversial decision, both fighters' gloves were seized by the state's boxing commissioner, and they remained in his collection for decades. In February 2015 both pairs worn by Ali and Liston sold together at Heritage Auctions for $956,000.

1) Floyd Patterson first fight gloves

(Image: Boxing News Online)

In November 1965 Ali defended his heavyweight title against former champion Floyd Patterson in Las Vegas. Prior to the fight, Ali criticized Patterson for refusing to call him by his new name, instead using 'Cassius Clay' which Ali referred to as his "slave name".

Patterson, who was mourning the sudden death of his coach, also went into the fight with an injury, and was clearly outmatched from the start. But perhaps in payback for the insult, Ali refused to end the fight quickly and toyed with Patterson before finally knocking him out in the 12th round. After the fight many sports writers and observers criticized Ali for unnecessarily humiliating Patterson in the ring.

The gloves worn by Ali during this contentious fight were bought by Ultimate Fighting Championship CEO Lorenzo Fertitta in 2014 during a charity auction is Las Vegas, for $1.1 million – the highest price ever paid for a piece of Muhammad Ali memorabilia.