After donning a suit and calling himself “Bond, James Bond,” Sean Connery became a fixture in countless conversations about Hollywood greats. The Scottish-born actor had a knack for playing a suave hero who could keep his cool when the fate of the world was on his shoulders. Audiences ate it up.

But in the early ’70s, beyond his Bond years, the Hollywood legend was distracted. Because unlike the spy he so famously played, Sean Connery didn’t benefit from movie magic in his daily life. When his mind fixated on something, he couldn’t pull out a fancy gadget to solve his problems: he was forced to sacrifice everything to get it.

When Sean Connery shows up in a movie, audiences know one of two things will happen: he’s either going to charm a lady, or he’s going to make things explode. Sometimes both. Oddly, his real life mirrored this pattern.

While playing James Bond (a role which saw him frequently charming and exploding things), the Scottish-born actor pulled a move that Agent 007 might’ve seen as dangerous: he fell in love.

MGM Studios

He married Diane Cilento in 1962, and together, they had one son. However, the relationship, according to Diane, was less like one between Bond and his girls, and more like that between Bond and Dr. No — there were serious struggles.

Diane felt that, in his post-Bond years, Sean grew jealous of her success as an actress. He allegedly became physically and emotionally abusive, even enjoying the company of many women who were not his wife. A 1972 golf trip highlighted the failure of the relationship.

While on a short vacation alone, Sean was taking some swings at a Moroccan golf club. There, he spotted a woman on the course he’d never met before. In that moment, a carnal desire ignited in his brain.

The woman was Micheline Roquebrune, a former teen golf legend. In her 20s, she traded 9-irons and putters for paintings and exhibits, making a career out of staging fancy art shows all over the world. Still, she hit the fairway often.

Though also married when Sean spotted her on the green, she, too, succumbed to the lust she felt when locking eyes with the legend. Later, when the sun had set, the two met in Sean’s quarters and, well, met in Sean’s quarters.

Over the next four days, Sean and Micheline never acknowledged the other while the sun was shining. At night, though? Well, the two met up again and again, forgetting about the failing marriages they certainly had to deal with when they went home.


Once the trip was over, Sean returned to Diane and his son, but he couldn’t shake Micheline from his mind. He was obsessed. Likewise, she returned to her husband and three kids, keeping an eye on Hollywood for a chance to see Sean once again. They didn’t speak for two years.


But then Sean’s and Diane’s relationship finally hit a wall. Unable to make their connection work, the two divorced in 1973. Before the ink on the divorce papers dried, Sean, still pining for Micheline, reached out to her.

He invited her to his home in Marbella, a Spanish resort city. A still-married Micheline scoffed at the offer. “Who does he think he is,” she recalled thinking to herself. But then, Sean spoke 14 words she’d never forget.

“I’ve missed you,” he said. “I can’t stop thinking about you, and I can’t forget you.” Convinced to take the plunge after a long gaze into his eyes, Micheline went to Spain, all but ending her marriage. Their romance was official — but right away, they hit problems.


“In the early days, it was difficult for us to see each other,” Sean recalled. “She was still living in North Africa with her children.” Nevertheless, they made time for each other, and soon they both knew it: they were in love.

In 1975 — just three years after their first meeting — Sean and Micheline wed in Gibraltar (oddly, at the same venue in which he married Diane). They’d sacrificed so much to be together, but Micheline still had concerns about Sean.

See, she was no dummy. She knew Sean was a serial womanizer, and she knew his wandering eye (for her) stuck a knife in the back of his last marriage. To keep their marriage long, happy, and prosperous, she set a few schemes into motion.

Though they lived permanently in Marbella, Sean spent a lot of time on movie sets. Micheline allegedly made sure she was right there with him, chasing away women with a proverbial wooden stick.

She even told Catherine Zeta-Jones to “butt out of it,” when the actress told tabloids Sean was a good kisser during a scene they’d shot together. “I knew I was taking on the whole package,” Micheline said of marrying Sean. “Everyone wants him, and I have to accept and understand that.”

Trust issues aside, the two put together a good life together, and over the next 40 years, their love prospered in a way their first marriages had not. “No man has ever had this effect on me,” Micheline said. “For the whole world, he’s a huge star, but for me, he is, above all, the man of my dreams.”

To keep their love alive, they make sure to enjoy breakfast and coffee together beside their villa’s pool. The little things aren’t lost on one of Hollywood’s biggest stars. “Micheline is an amazing woman,” he said. “She is the love of my life.”

Coincidentally, Sean’s longest lasting relationship looked like an affair ripped from a 007 movie. Yet surprisingly, he pulled his most James Bond-esque move decades earlier, before he ever donned the moniker. His actions would’ve made the intelligence agent proud.

It was sometime in the early 1950s, and Sean was playing billiards and chatting up a few lovely ladies at a crowded pool hall on Lothian Street in Edinburgh. As the story goes, he was wearing a really nice leather jacket.

What Sean didn’t realize was this pool hall sat squarely in the territory of the Valdor street gang, leather-clad tough guys who didn’t take kindly to new faces schmoozing up women — and wearing nice jackets — on their turf.

Edwardian Teddy Boy

In fact, Sean might’ve reconsidered his interest in billiards and women had he known the Valdor gang, through violence and terror, had earned a reputation as gentlemen you didn’t exactly want to bring home to meet your parents.

Anyhow, one of the Valdor boys walked up to young Connery, grabbed his jacket — which he’d taken off while playing — and threw it on the ground. His message to Sean was clear: get out of here, pretty boy.

A weaker man — or maybe a more sensible one — might’ve withered at this. He might’ve gathered his crumpled jacket from the floor, given a subtle nod to his friends, and run out the front door. Sean did not do this.

Instead, Sean raised his pool cue like a knight might raise a sword. “I’ll give you five seconds to put that back,” Sean said, nodding to his jacket, his knuckles turning white as he clenched his weapon of choice.

First Knight

Perhaps a tense staredown followed. Perhaps the next few seconds felt like half a century to the Valdor boy, who considered what the repercussions might be if he sunk a fist into the future James Bond’s jaw right there.

Right then, however, the gangster backed down. As he fled the club, thoughts of revenge raced through his mind. There was no possible way, he concluded, someone could come into his pool hall and disrespect him like that.

So the gangster gathered five friends, and a few days later, the group of six men tracked Sean down to the Fountainbridge Palais, a nightclub where Sean worked as a bouncer.

Edin Photo

The plan for the gangsters was simple: they would walk up to Connery, pummel him until his face looked like a pizza that’d been dropped off a ten-story building, and then leave. Maybe they’d even get to symbolically swipe his jacket.

Pilot Online

But there were a few things that these gangsters didn’t take into account when they hatched their revenge plot. See, while we might know Sean as an actor — an artist — back then, he had other ambitions.

At the age of 18, Sean started training to become a bodybuilder. After two years, he began working with a former gym instructor for the British Army. To fund his ambitions, he took on labor-heavy jobs.

He lugged bottles as a milkman, swam long distances as a lifeguard, and kept the peace throughout clubs and bars in Scotland as a bouncer. In 1950, strapping young lad that he was, he competed for Scotland in the Mr. Universe contest.

He won third place, but even so, there was no denying Connery’s strength and size. As his good friend and fellow actor Michael Caine said, at this time, Sean looked like a “Scottish Arnold Schwarzenegger.”

Cinema Metro

It was this absolute monster of a man the Valdor gang approached outside the nightclub. When they made their intentions for a fight clear, Sean Connery, a non-violent guy by all accounts, climbed onto a 15-foot high balcony, hoping to escape.

The Valdor gang pursued, however, and before Sean knew it, he was on a balcony 15-feet up with nowhere to hide. He couldn’t run, so there was just one option left: fight.


And fight he did. At one point, with the powerful calloused hands of a champion weightlifter, Sean grabbed one of the gangsters by the throat and squeezed; with the other hand, he grabbed another by the biceps.

In total control of these two gangsters, he slammed their heads together. The ensuing crack of their skulls colliding probably sounded something like banging two coconuts together.

Nearly 70 years later, we only know a few details from the fight. All surviving eyewitness accounts, however, make the same claim: Sean Connery absolutely annihilated these six gangsters.

When the fighting finished, Sean Connery stood tall over the six leather-clad men. This had an odd effect on the gangsters. So used to their utter dominance of the streets, they couldn’t help but respect the man who’d kicked all of their butts.

Virtual Jerusalem

So the Valdor gang, flushed with respect for Connery, offered him a spot within their ranks. He politely declined, but the Valdor gang knew he was someone to be respected.