Michael is shown to be an incompetent manager, who injects a lot of his personal feelings into the work environment. He seems to have few relationships outside the office. In his interactions with other characters, he is shallow, callous, ignorant and unaware of basic social norms. He tends to overestimate his own importance in the eyes of his co-workers and cannot understand why they do not seem to have much fun at work, as he believes an office to be the "place where dreams come true." However, Michael is somewhat loyal to the company and honestly tries to help his employees when he thinks they are having a problem. Michael has been at Dunder Mifflin (as of "Michael's Last Dundies") 9,986,000 minutes, meaning he would have been working at Dunder Mifflin since May 6, 1992.

William Lumbergh is a fictional character, who appeared initially in the animated shorts Milton, and later was portrayed by Gary Cole in the 1999 film Office Space. A caricature of corporate management, Lumbergh is the division Vice President of the software company Initech, and serves as the main antagonist of the film.

Lumbergh is a micromanager who is focused on pointless paperwork, notably TPS reports; he has been described as "the antithesis of the motivational management leadership ideal". He uses "What's happening?" as a greeting, and when asking an employee to do some unpleasant task starts his sentences with, "m' yeah, I'm gonna need you to" or "if you could just go ahead and", as well as ending these requests with "That'd be great" and "Mmmkay?". A Wharton Journal perspectives article opines that the character "brilliantly exposed the emptiness of linguistic conventions at work." Social historian Joe Moran writes that Lumbergh's "non-confrontational" communication style "masks the reality of management coercion".

Donald John Trump, Sr. (born June 14, 1946) is an American business magnate, author, and television personality. He is the chairman and CEO of The Trump Organization, a real-estate developer based in the United States. Trump is also the founder of Trump Entertainment Resorts, which operates numerous casinos and hotels worldwide. Trump's extravagant lifestyle and outspoken manner have made him a celebrity for years, and more recently with his NBC reality show The Apprentice, where he serves as host and executive producer. In 2010, Trump expressed interest in becoming a candidate for President of the United States in 2012. On May 16, 2011, he announced he would not run. On May 23, he stated he has not completely ruled out running if no viable Republican Party candidate emerges. In 2011, Trump ranked No. 17 on the Forbes Celebrity 100 list.

Trump is the fourth of five children of Fred Trump, a real-estate tycoon and developer based in New York City. Donald was inspired to follow his father into real-estate development, and began working on projects for his father's real-estate firm while still in college. Upon his graduation from the Wharton School of the University of Pennsylvania in 1968, Trump formally joined his father's company, Elizabeth Trump & Son. He took the helm in 1971 and renamed it The Trump Organization.

George Michael Steinbrenner III (July 4, 1930 – July 13, 2010) was the principal owner and managing partner of Major League Baseball's New York Yankees. During Steinbrenner's 37-year ownership from 1973 to his death in July 2010, the longest in club history, the Yankees earned 7 World Series titles and 11 pennants. His outspokenness and role in driving up player salaries made him one of the sport's most controversial figures. Steinbrenner was also involved in the Great Lakes shipping industry.

Known as a hands-on baseball executive, he earned the nickname "The Boss." He had a tendency to meddle in daily on-field decisions, and to hire and fire (and sometimes re-hire) managers. Former Yankees manager Dallas Green gave him the derisive nickname "Manager George."

He died after suffering a heart attack in his Tampa home on the morning of July 13, 2010, the day of the 81st All-Star Game

Allen "Al" Davis (born July 4, 1929) is an American football executive, who currently serves as the principal owner (titled as "president of the general partner" or "managing general partner," depending on the source) of the NFL's Oakland Raiders.

Gordon Gekko is the main antagonist of the 1987 film Wall Street and the antihero of the 2010 film Wall Street: Money Never Sleeps, both by director Oliver Stone. Gekko, a fictional character, was portrayed by actor Michael Douglas, whose performance in the first film won him an Oscar for Best Actor.

Co-written by Stone and screenwriter Stanley Weiser, Gekko is claimed to be based loosely on arbitrageur Ivan Boesky, who gave a speech on greed at the University of California, Berkeley in 1986, and real-life activist shareholder and corporate raider Carl Icahn. According to Edward R. Pressman, producer of the film, "Originally, there was no one individual who Gekko was modeled on," he adds. "But Gekko was partly Milken", who was the "Junk Bond King" of the 1980s, and indicted on 98 counts of racketeering and fraud in 1989.

In 2003, the AFI named him number 24 of the top 50 movie villains of all time.

Miranda Priestly, the British-born (as Miriam Princhek) editor-in-chief of Runway, a very chic and influential fashion magazine published by the Elias-Clark company. She is known for wearing a white Hermès scarf somewhere on her person every day and treating her subordinates in a manner that borders on emotional and psychological abuse.
People at the magazine are afraid of finding themselves alone in an elevator with Miranda, or making critical remarks about her even to their close friends. Andrea dubs this attitude the Runway Paranoid Turnaround, as whenever one of her co-workers makes the slightest negative comment about Miranda, they immediately follow it up with a "turnaround" positive comment, due to their fear of their boss finding out about their attitude and firing them.

Angelo R. Mozilo (born 1938) was the chairman of the board and chief executive officer of Countrywide Financial until July 1, 2008. Condé Nast Portfolio ranked Mozilo second on their list of "Worst American CEOs of All Time".
Over many years, Mozilo sold hundreds of millions of dollars in stock personally, even while publicly touting the stock and using shareholder funds to buy back stock to support the share price. On June 4, 2009, the U.S. Securities and Exchange Commission charged former CEO Angelo Mozilo with insider trading and securities fraud.

Dr. Kenneth Lee "Ken" Lay (April 15, 1942 – July 5, 2006) was an American businessman, best known for his role in the widely reported corruption scandal that led to the downfall of Enron Corporation. Lay and Enron became synonymous with corporate abuse and accounting fraud when the scandal broke in 2001. Lay was the CEO and chairman of Enron from 1985 until his resignation on January 23, 2002, except for a few months in 2000 when he was chairman and Jeffrey Skilling was CEO.

Bernard John "Bernie" Ebbers (born August 27, 1941) is a Canadian-born businessman. He co-founded the telecommunications company WorldCom and is a former chief executive officer of that company.

In 2005, he was convicted of fraud and conspiracy as a result of WorldCom's false financial reporting, and subsequent loss of US$100-billion to investors. The WorldCom scandal was, until the Madoff schemes came to light in 2008, the largest accounting scandal in United States history. He is currently serving a 25-year prison term at Oakdale Federal Correctional Complex in Louisiana. Portfolio.com and CNBC named Ebbers as the fifth-worst CEO in American history; Time magazine named him the tenth most corrupt CEO of all time.

Leonard Dennis Kozlowski (born November 16, 1946, Newark, New Jersey) is a former CEO of Tyco International, convicted in 2005 of crimes related to his receipt of $81 million in purportedly unauthorized bonuses, the purchase of art for $14.725 million and the payment by Tyco of a $20 million investment banking fee to Frank Walsh, a former Tyco director. He is currently serving 8.33 to 25 years at the Mid-State Correctional Facility in Marcy, New York. His earliest release date is January 17, 2014, when he becomes eligible for parole.