The Scariest Bosses Of All Time

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HELMSLEY SUED (Surrounded by her attorneys Jeffrey Taub, left, and Steven Eckhaus, right, Leona Helmsley speaks to the press out
APThe late Leona Helmsley, notorious "Queen of Mean"
The employee-boss relationship is automatically scary for any worker. These are the people, after all, who control destinies. But some managers are simply more frightening than others. And this is the season for frights and scares.

So see below for eight of the most memorable scary bosses America has ever known. Would you dress up as any of them for Halloween?

Scariest Bosses Of All-Time
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The Scariest Bosses Of All Time

Photo: Sunbeam Corp. CEO Al Dunlap during a 1997 meeting in Boca Raton, Fla. 

When your boss is nicknamed "the Chainsaw" it shouldn't come as a surprise when he proves to be a nasty one. And over the course of his career, Al Dunlap did much to earn the savage nickname. Back in 1994, he engineered a "restructuring" at Scott Paper over a 20-month period that left 35 percent of the workforce, or 11,000 workers, out of work. Of course everyone knows tough decisions have to be made in business, but Dunlap's approach to the bloodletting could hardly be described as sensitive.

For starters, he walked away with $100 million as a result of the headcount reduction, as Business Insider reported. And he capitalized on his strategy to build his own brand, writing a best-selling book called, "Mean Business." He would later be caught fudging sales stats during a stint atop Sunbeam, which was filed for bankruptcy in 2001, as Time Magazine reported.

(Disclosure: This writer was the author of the Time Magazine piece on Dunlap.)

Photo: Cincinnati Reds owner Marge Schott attends a Reds game at Riverfront Stadium in 1995

You expect your boss to have role models. You just hope they aren't modeling their leadership style after Adolf Hitler's. Yet the former leader of Nazi Germany had an admirer in the former owner of the Cincinnati Reds, Marge Schott. Back in 1992, and two years after her Reds won the World Series, Schott told the New York Times the following about Hitler: "Everybody knows he was good at the beginning, but he just went too far."

Over the next few years, she would make similar remarks while also directing her bigoted venom at African-Americans, among other groups. As a result, she would be subject to various suspensions by Major League Baseball before she was forced to relinquish daily control of the Reds in 1996.


Photo: Leona Helmsley is escorted from State Supreme Court by her attorneys in 2003

You don't get dubbed the "queen of mean" for nothing. A daughter of Polish immigrants, Leona Helmsley made it in her own right in New York's real estate world before she married Harry Helmsley in 1972.  But in spite of their combined billions the Helmsleys had a distaste for taxes, it turned out. In 1983 the couple set out to renovate a mansion in Connecticut but tried to illegally list costs as a business expenditure to lower their taxes. When the conduct came to light the Helmsley's maid claimed she heard Leona say, "We don't pay taxes. Only the little people pay taxes."

This haughtiness was in fact a day-to-day reality for those who worked under Helmsley. In one famous incident, Helmsley was said to have taken a tea cup and smash it on the ground at one of her hotels before demanding the waiter to get on his knees and beg to keep his job, as was described by Mental Floss. Why was such imperiousness necessary? Because water had spilled from the tea cup onto the saucer. And most famously, when she died, Helmsley left $12 million to her dog, as was reported by the New York Times.

Photo: New York Yankees owner George Steinbrenner munches on a snack during a 2007 Yankees game

When you hire and fire the same worker five times in one lifetime, you should expect everyone else around you will be intimated. That's the tally for George Steinbrenner, the onetime owner of the Yankees, and his on-again off-again club manager, Billy Martin. Indeed, personnel turnover was a hallmark of Steinbrenner's stewardship of the Bronx Bombers. Following Steinbrenner's purchase of the team in 1973 the next sixteen years would see 19 managers come and go, in addition to  15 pitching coaches and 13 general managers, as Time Magazine reported.

Steinbrenner was also famous for his micromanagement, concerning himself with matters like his players' facial hair. He also snooped on a player of his in an incident that got him suspended. "The Boss," however, was also a winner; his Yankees claimed seven World Series titles during his 37-year ownership of the team.


Photo: Blanck and Harris outside the Triangle Waist Company

A humane boss allows workers to also be human beings, which means employees are given the right to go outside for a breath of fresh air. But for Blanck and Harris, the owners of the Triangle Shirtwaist garment Company, there was no room for their workers to do even that. In all fairness, such a policy was more common during their careers in the early days of the 20th Century; bosses used the strategy to prevent employee theft, as PBS reported. But the locked-door policy famously came to a head in 1911 when their factory caught fire. A total of 146 workers died in the fire, causing the single worst loss of life in New York City before Sept. 11.

Photo: George Pullman, the inventor of railroad cars with folding berths

All workers are concerned about the extent to which their managers controls their lives. Now imagine if you worked for railroad baron George Pullman, who literally forced his workers to live together in the same town, located just south of Chicago, while he controlled their every move during the late 19th Century.

The workers lived in a pseudo-kingdom in the town, in which there was no free press or right to public assembly. Pullman also sent in inspectors to check the cleanliness of his workers' houses. How did he manage to maintain such control over his workers? Pullman deducted rent from his employees' paychecks at the Pullman Palace Car Co, as Time Magazine reported.

Photo: A file photo of Hoover from 1971

Hoover was the very first director of the Federal Bureau of Investigation (FBI) and went on to hold the top post from 1935-1972. And ever since the FBI has limited the time its leaders can serve to 10 years. Indeed, during his reign Hoover maximized his control over his staff. He's said to have looked at the Bureau as if it were his own personal help, ready at any moment to pursue any paranoid request he made. He even once reportedly forced a staffer to get a feces specimen that was left on his patio inspected; he was convinced he was being followed by a wild animal. He then went so far as to build a trap for the suspected animal, but in the end the only victim was his neighbor's cat, which died in the trap, according to the Independent.

Hoover, of course, worked through the Cold War era, which was known for its skullduggery. And Hoover was a master at the great game, famously compiling secret files on romantics liaisons of the rich and powerful to be used for blackmail and other dark arts.

Photo: File photo of Henry Frick

You don't get a major New York City museum named after you by simply being a nice guy. In fact, no one would ever confuse Henry Frick for a pleasant person; he was even voted America's most hated person during his lifetime, which spanned from 1849 to 1919, largely because of his leadership style as chairman of the Carnegie Steel Company.

There are many tales of his ruthlessness, but perhaps none was as maddening for his workers as his conduct during the strike at the steel plant in Homestead, Pa., in 1892. At the time workers in many industries, including copper and coal, were protesting for greater rights, as PBS reported. When the activism arrived at a Carnegie plant Frick responded by building a fence three miles long and twelve feet high around the plant. The fence had peepholes to allow for rifles to fit. After Frick announced his refusal to negotiate over wages, tensions mounted. Finally, Frick sent in the private Pinkerton army to control the plant. Nine workers were killed in the melee. 

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