The 5 biggest badasses in Shanghai history

The 5 biggest badasses in Shanghai history

Every city has its share of historical renegades, but somehow Shanghai's have always been a little more, shall we say, intense. Here are five that might just make you whimper a little bit

Culturally and politically, few places have seen more dramatic shifts over the past two centuries than Shanghai. It has been a meeting place for international thoughts and ideas, a theater in which competing international interests played out with fascinating and often tragic consequences. 

But it has also been a city flush with sex, drugs and violence, ranking high on the list of historically badass cities. And this delicious debauchery is not the result of just one or two renegades (one badass does not a 'whore of the Orient' make). Shanghai has been run through with badasses throughout the ages, ranging from the hard-nosed to the certifiably insane. This list, in keeping with the city’s cosmopolitan mystique, looks at five badasses from various nations and eras, each weaving his own thread in the city’s rich, roguish tapestry. 

Big Ears Du Visible here: Green Gang top-brass with Zhang (center), Huang Jinrong (left) and 'Big Ears' Du (right). Not pictured: The shrunken monkey skulls Du wore under his robe.1. The Green Gang, opium-running gangsters

The Green Gang was epically badass. Triads, opium smugglers, Chiang Kai-shek’s murder squad, moles inside every police station… where to begin?

Most contemporary experts would attribute their awesome intimidation qualities to leaders 'Big Ears' Du Yuesheng and Zhang Xiaolin. The smoother Du metaphorically flexed his badass biceps by delivering coffins to his enemies’ homes, whereas the bat-shit crazy Zhang supposedly fed his girlfriend to a tiger.

Earlier boss 'Pockmarked' Huang Jinrong may not have been quite as memorable, but did have the redeeming quality of a great gangster nickname. 

Badass quote: “You need two things to survive in this world: courage and wisdom.” -- Du Yuesheng


Chen YiBadasses on the level of Chen Yi thrive on conflict and have been known to go to extreme lengths -- such as dressing like a bellhop -- in order to provoke confrontation.2. Chen Yi, new Shanghai’s enforcer

If the Green Gang was the baddest of the badasses in a city dripping with badassery, then the man that managed to silence them must have been very badass indeed. The spicy Sichuanese Chen Yi was a CCP strongman and a gifted military mind. He marched the Long March, resisted the Japanese and commanded the decisive Red Army victory over the KMT at Huaihai. He was named the first Communist mayor of Shanghai, where, among other things, he eradicated prostitution, gambling, opium and organized crime. No small feat in those days.

Unfortunately being a mean son of a bitch rarely went unpunished in Mao’s China, and Chen was demoted from China’s top diplomat to a janitor, cleaning toilets in Beijing for the rest of his life. In a cruel twist of fate, each day his proud statue on the Bund is mistaken by thousands of tourists for Mao Zedong.

Badass quote: “Chen Yi is a good and loyal comrade.” -- Chen Yi’s colossally badass (and complete B.S.) response during a Red Guard interrogation when asked what was Mao’s wisest saying.

Frederick Townsend Ward19th century super-badass Frederick Townsend Ward always wore the same costume, seen here, to battle and never carried any weapon besides a stick.3. Frederick Townsend Ward, Taiping killer

The few facts that we do know about 'General' Frederick Townsend Ward read like a chapter out of the badass handbook. A Massachusetts-born soldier of fortune with a resume that included pirate-hunting in Asia, working as a ranger in Mexico and soldiering in the Crimea, Ward would become the savior of the Qing Dynasty.

Legend has it that the minute Ward got wind of the civil war raging in China between the Taipings and the Manchus, he rode his horse from the East Coast of the United States to San Francisco, boarding the first boat bound for Shanghai. Rounding up whatever foreign mercenaries he could find, Ward got his ass handed to him (twice) at Taiping-held Qingpu, taking a bullet in the face on the second try. He was arrested for violating Western neutrality laws, escaped Steve McQueen style and trained thousands of Chinese soldiers. And he trained them well. Ward’s “Ever-victorious Army” kept the 120,000 advancing Taipings from taking Shanghai and -- though Ward didn’t live long enough to see it -- later crushed the rebellion.

Badass quote: “The Rebels had, we heard, been met and defeated with tremendous slaughter, and by whom? By a native force, admirably drilled… by our lately despised American filibuster, General Ward… It must have been with grim satisfaction that Ward awoke, the morning after this battle, to find himself a hero.” -- Augustus Hayes, Shanghai businessman

Yun Bong-gilYun Bong-gil with a birthday present for Emperor Hirohito.4. Yun Bong-gil, Korean freedom fighter

In early 1932, as the Chinese areas of Shanghai were invaded by the Imperial Japanese Army with little pretence, a Korean badass emerged. Yun Bong-gil was a member of the Korean Patriotic Association, a group determined to make a stand against the army that had for decades occupied their home country and was now setting its sights on China. 

On the Emperor Hirohito’s birthday celebration in what is now Lu Xun Park in Hongkou District, Yoon launched a bomb disguised as a water bottle at a group of high-ranking Japanese military brass, killing several of them instantly. His badassery earned him a prompt execution in Japan, and he is now enshrined in a small museum at Lu Xun Park.

Badass quote: "A young Korean patriot has accomplished something tens of thousands of Chinese soldiers could not do." -- Generalissimo Chiang Kai-shek

William E. FairbairnFairbairn demonstrates the delicate art of stabbing some jerk in the butt.5. William E. Fairbairn, hard-boiled cop

Officer WE Fairbairn was as close as Shanghai has ever gotten to producing a hardened badass in the Schwarzenegger mold. In the course of this mean son-of-a-bitch’s prolific 33-year career on the Shanghai Municipal Police Force, he was involved in 600 recorded combat situations. No that wasn’t a typo. 600 fights! This guy wrote the book on kicking ass, several of them actually, with testosterone-infused titles like "Defendu," "Get Tough" and "Shooting to Live." He even helped design a weapon (with another SMP officer) used by British commandos in WWII, the Fairbairn-Sykes Fighting Knife. 

Badass quote: “Unarmed combat is what we enter into when we have been foolish enough not to have a weapon; careless enough to lose our weapon, or unlucky enough to have broken our weapon.” -- W.E. Fairbairn