Impresario Vince McMahon, the Chairman of World Wrestling Entertainment and the Czar of professional wrestling in America since the 1980s, presented champion wrestlers Ric Flair and Shawn Michaels with Rolex watches. As Wrestling 101 reported in April of 2008, “Vince McMahon gave Ric Flair and Shawn Michaels Rolex watches. Both watches were inscribed with “24,” with Flair’s saying “To Be the Man,” and HBK’s saying “You Gotta Beat the Man.” Classy move by Vince.â€� Giving the Rolex watches revealed that McMahon could overcome his past resentments and feuds. In November 2001, Ric Flair returned to WWF after an 8-year hiatus saying that he was the co-owner of the WWF. McMahon hated this and said that he was the only owner of the WWF. The two faced each other at Royal Rumble 2002 in a Street Fight, which Flair won. On the June 10, 2002 edition of Raw, McMahon defeated Flair to end the rivalry and become the sole owner of WWE. Moreover, McMahon’s feud with Vince Michaels is legendary, including betrayals, sneak attacks and dirty battles with his son Shawn McMahon. Showing his true pride and glory, McMahon transcended the violent and sordid past with a magnificent gift of two diamond-studded, jewel-encrusted Rolex watches to Flair and Michaels.

Beyond the realm of Vince McMahon, Rolex always has played a strange role in professional wrestling. A Rolex watch has often been a wrestler’s symbol of success and luxury. Naturally, such a symbol becomes a target for the wrestler’s opponent. In the Wrestling Booking Sheet, Michael Cole wrote, “Mankind said he was dominating The Undertaker’s gang when The Rock came in. The Rock said he broke his Rolex for Mankind.â€� Yes, wrestlers have been known to destroy a precious Rolex wristwatch on camera in order to intensify a feud with another wrestler. Would anything make you angrier than having your Rolex Day-Date President or your Rolex Oyster Datejust Jubilee crushed right in front of your very eyes?

Vince McMahon is not the only major executive in the wrestling world to wear a Rolex. The following excerpt is taken from the Los Angeles Times in 1999: “Eric Bischoff, Turner’s wrestling chief, ponders how to make chicken salad out of a crisis that beset his World Championship Wrestling’s pay-per-view the night before. . . “You know we wouldn’t do something that looks like some manipulative ratings ploy, now would we?” Bischoff asks. Then he takes off his Rolex, dons his leather jacket and prepares to go before a sold-out arena in Phoenix to assume his on-screen persona–of a smirking, scheming wrestling czar.â€� What is so intriguing is the story represents another side to the proverbial coin: Bischoff’s Rolex is his own watch that represents his real world success in his personal life. In order to enter the crazy world of professional wrestling, the top executive removes and protects his Rolex watch, as he morphs into the crazy character he becomes on television. Indeed, Rolex and professional wrestling make for a strange marriage, but they have walked down the aisle for quite some time and, most likely, will continue to do so for many years to come.

Rolex is the new champion in the auction house, certifying the watch company’s legendary position as the creator of the highest quality wristwatches. On April 23, 2008, an ultra-rare 1971 “Albino� Rolex Daytona, formerly owned by rock n’ roll legend Eric Clapton, sold at Sotheby’s “Important Watches Auction� for $505,000 including buyer’s premium. Although it was expected to fetch $100,000-$150,000 by watch experts, the Rolex Daytona broke all records when it sold for over half a million dollars once the dust had settled.

Created by Rolex in 1971, the watch is nicknamed the “Albinoâ€� Daytona because the background and subsidiary dials are a monochrome silver color, in stark contrast to the normally contrasting dials of more common Rolex Daytonas. It was a design that was not too popular, as the contrasting outlined sub-dials make for better visibility. If you look at the Rolex Daytona models today, they have no “Albino’s”. Basically, the watch was an unpopular variant of a popular model. Before the auction, the Rolex Daytona was not even expected to be in the top three of most expensive watches sold on that day. At this auction, the 6th most expensive watch sold was a “James Bondâ€� Rolex Submariner from 1959, which brought in $211,000. The 2nd through 5th most expensive watches sold at this auction belonged to Pate Philippe and ranged from $217,000 to $445,000. At the Antiquorum’s recent $8.5 million Rolex auction, the top-priced timepiece sold for $248,000.

For years, Eric Clapton has been recognized as a major Rolex watch collector. The guitar legend’s personal collection is quite extensive, and Clapton even named his record collection of greatest hits, Timepieces. Still, nothing in Clapton’s collection compares in price to the 1971 Rolex “Albino� Daytona, which will now go down in history as the Rolex that shocked the refined world of high-priced auctions.

Before being deposed by American forces and executed by his people, Iraqi Dictator Saddam Hussein was known for his love of luxury, clearly represented by his custom-made, diamond-studded gold Rolex watch. Unlike the majority of Hussein’s loot, the Rolex watch did not end up in the hands of the American military. Instead, Saddam’s right-hand man Haitham Wahaib is putting the Rolex up for auction, along with other valuables, in order to raise $4500,000 for Iraqi schools. But how did Wahaib end up with the Rolex in the first place? Although his tale appears incredulous on the surface, it is worth repeating. As reported by Mark Nicol in The Daily Mail, the story is as follows:

It was the most lucrative day’s work that Haitham Wihaib will ever do. His boss Saddam Hussein had just spent hours in a Baghdad palace with one of his many mistresses. As the Iraqi dictator emerged and headed towards his chauffeur-driven Mercedes, it was Wihaib’s job - as his head of protocol - to check that he had not left anything behind. “To my surprise I saw his £100,000 gold Rolex sitting on a bedside table,” recalled Wihaib. “I ran after Saddam and stopped him just before he got in the car. I said, ‘Your Excellency, your Excellency, you left your gold Rolex behind.’ When he turned to me, I had never seen such a satisfied look on his face. He had clearly had a very pleasurable afternoon. He smiled and told me to keep it.”

The custom-made Rolex has dozens of diamonds laid into the watch face and the bracelet. At the very pinnacle of luxury, the watch represents the incredible quality and precision of the Rolex watchmakers. The Daily Mail confirmed that the watch is genuine and the valuation is accurate. Long before the Iraq war that led to Saddam’s fall, Haitham Wihaib had a bad falling out with his master and was imprisoned. After being released, he managed to smuggle his collection of Saddam’s valuables out of Iraq and defect to Great Britain in 1994. Although he worked for the dictator for over twenty years and was his chief of protocol, Wihaib has never worn the gold Rolex given to him by the Iraqi dictator. In regards to his hiding of the watch, Wihaib said: “All Saddam’s bodyguards were very jealous so I never wore the Rolex in Iraq. They would have chopped my arm off for such a watch.�

In closing, it is fascinating to note that Saddam’s regime often altered expensive Rolex watches with faceplates depicting the leader. Amazing as it sounds, these symbols of Western power and affluence were greatly admired by members of the anti-Western Ba’ath party or so the story goes. Although Saddam Hussein would deface a Rolex watch given to his supporters, the authenticity of his own custom-made Rolex was kept and maintained. It will be intriguing for Rolex enthusiasts to see how high the price goes for Saddam’s jewel-encrusted Rolex watch.

Before their divorce in October, Guy Ritchie celebrated the 50^th birthday of his wife Madonna by giving her a $100,00 vintage Rolex Masterpiece watch. At the huge party Guy Ritchie threw for Madonna in August, nobody knew the couple was on the verge of separating. In fact, they might not even have known that their marriage rapidly was coming to a close. As Central Park Gossip reported: “Superstar Madonna’s hubby Guy Ritchie has made sure his wife is on time for all her birthday appointments, he’s bought her a $100,000 Rolex watch to celebrate the day. The movie maker has reportedly bought the Material Girl an 18-karat gold and diamond-studded Rolex Masterpiece as a 50th birthday gift. A pal tells In Touch magazine, ‘She (Madonna) wanted it for a while, but she couldn’t bring herself to spend that much money on a watch.’ “

At the celebration, Guy Ritchie gushed about his wife in front of nearly a hundred well-wishers: “She looks better now that she ever had done. I’m so proud. I love her so much.â€� The party included cases of champagne and mounds of caviar with illusionist David Blaine performing card tricks for the guests. In Touch magazine had a different take on the party at the time, believing, “Guy picked up a $100,000 diamond-covered Rolex for Madonna, because nothing says “I love you” quite like marking a major age milestone with a device that measures the passage of time.â€�

Although the Rolex Masterpiece given to Madonna was not caught on camera, a similar piece pictured above recently was put up for sale at a major estate auction and described as follows: “The centerpiece item in the estate jewelry group is an original factory Rolex Masterpiece 18k white gold ladies’ watch, brand new in the box with papers, with factory diamond bracelet, factory diamond bezel and factory mother of pearl and diamond dial. It is the finest ladies’ watch Rolex makes. Very few are produced, and anyone lucky enough to find one would probably pay around $100,000.�

Madonna reportedly was thrilled by her beautiful Rolex Masterpiece, but the high of the party quickly sank into the depths of divorce. By the end of October 2008, the marriage of these two high profile celebrities was over and officially ended at a short proceeding in a London courtroom. Although Ritchie spent lavishly on his wife for her 50^th birthday, including the $100,000 Rolex Masterpiece and a half million-dollar Bulgari necklace, he walked away from the marriage with a hefty seventy million dollar settlement. The remaining question is whether Madonna will wear her beautiful Rolex Masterpiece, or will she place it in a safe deposit box in order not to be reminded of her lost love?

Matt Damon believed in Rolex in the beginning, and such loyalty has remained even beyond the marketing deals of his successful film series. No matter what kind of watch the producers give Jason Bourne, Matt Damon wears a Rolex in his private life and gives Rolexes as incredibly generous gifts. But even Amazon.com knows Jason Bourne should be wearing a Rolex as expressed in a review of the last film on the Amazon site that, “with careful attention to detail and a plot that works like a Rolex, Ultimatum’s unrelenting pace never feels overblown.� The comparison makes perfect sense because no other luxury watch has both the dedication to quality and the record of accomplishment of a Rolex. When it comes time to surprise old friends, Matt Damon remembers this truth about the legendary wristwatch.

In 2002, the following story was reported in the London Sun: “Matt Damon went to a college reunion – and bought each of his 36 classmates a £2,200 Rolex watch. 
The Hollywood heartthrob’s generous gesture cost him almost £80,000. A pal said: “He wasn’t showing off – he just wanted to let friends know he hadn’t forgotten about them. It was a shock when he turned up. Everyone thought he would be far too busy hob-nobbing with the rich and famous.� What kind of Rolex Matt gave his classmates remains a mystery, but his generosity remains admirable and impressive. 

In his own life, Matt Damon wears a vintage Rolex Oyster Perpetual Explorer 1016, perhaps the most collectible of the Rolex watches. In the shot at the poker table, Matt wears his Rolex Explorer. After reviving the poker movie genre and poker in general with Rounders, Matt became an avid player in his private life. He wears a Rolex at the tables because the watch reminds him of the precision and focus needed to win when playing against the very best.

Matt’s Rolex Oyster Perpetual Explorer 1016 has “Superlative Chronometer Officially Certified� written above the six o’clock marker. Fitted on a Rolex solid link oyster bracelet, the watch has a black matte dial and is powered by a Rolex caliber 1570 rotor automatic. In a recent photo shoot with GQ, Matt is wearing another Rolex, but the only identification the magazine supplies is, “Watch by Rolex.�

At the beginning of the 21^st century, AskMen.com noted that, “Matt Damon is reportedly set to become the new face of Rolex watches. Sources claim the hunky actor is currently in talks with bosses about signing a lucrative deal to advertise the luxurious watches. A source said: “He’s hugely popular and would be brilliant as the face of Rolex.â€� Unfortunately, such a deal was never consummated, but Matt’s belief in and dedication to Rolex has never wavered, and the actor continues to wear and give the watches to this very day.