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How Dean Winters Achieved a Net Worth of $6 Million

You have probably seen Dean Winters on TV or in the movies. But do you know how much he is worth? From his television and film credits, as well as from commercial work, Winters has amassed a net worth of $6 million.

Are you curious how he did it? Read on to find out more. 

Early life

Winters was born on July 20, 1964 in New York City. As befits his Irish and Italian heritage, he speaks fluent Italian. He has two brothers, Scott and Bradford, and a sister, Blair.

After graduating from Brophy College Preparatory, a Jesuit, Catholic school in Phoenix, Arizona in 1982, he was graduated from Colorado College in 1986.

Homicide: Life on the Street (1995)

Winters' first credit on television was for portraying Tom Marans on Homicide: Life on the Street. The NBC show about the Baltimore Police Department ran from 1993 to 1997. The show changed television history, and the police procedural genre, by giving a prominent focus to racial tensions and power dynamics.

It is thought that the show was based on a David Simon book, Homicide: A Year on the Killing Streets, which came out a few years prior in 1991.

OZ (1997-2003)

While Winters was working on establishing his career, he worked as a stand up comic. Winters toured around the country and performed at some of the biggest and best known comedy venues in America, including Catch a Rising Star, The Comic Strip, and the Comedy Cellar.

He occasionally was on the same billing as comedians Jerry Seinfeld, Paul Reiser, and Chris Rock.

It was while doing stand up comedy that he secured an HBO comedy special. A casting agent for OZ, a prison drama shown on HBO, saw his comedy special and cast him for the role of Ryan O'Reily. O'Reily was an inmate in a special unit, known as Emerald City, within the Oswald Maximum Security Prison.

The premise of the show was that O'Reily and the other prisoners could be rehabilitated instead of simply being punished. It earned several awards, including the PASS Award, Webby Award, Banff Rockie Award, and ALMA Award.

Divorce (2006-2009)

Winters next appeared on Divorce,  an American comedy-drama television series that ran on HBO. Set in Hastings-on-Hudson, New York, it starred Sarah Jessica Parker and Thomas Haden Church.

Winters played Tony Silvercreek, a reoccurring character. Critics liked the dark humor of the show, as well as the chemistry between the cast members. 

Brooklyn Nine-Nine (2013-2019)

In his next television appearance, Winters played a cop in the New York Police Department's Major Crimes Unit named Keith Pembroke. His was not a likable character and was often sexist, arrogant, obnoxious, and self-centered.

He earned the nickname "The Vulture" at the unit by frequently swooping in when the case was nearly wrapped up and then taking the credit for solving it.

Battle Creek (2015)

Winters then moved on to another cop show, Battle Creek, in 2015. He played Russ Agnew, a jaded detective who was mismatched with a charming FBI agent. The two were charged with solving a drug related murder, but the show was canceled after only 13 episodes.

Hellraiser: Hellseeker (2002)

Winters' first movie was Hellraiser: Hellseeker, a 2002 supernatural harrow film. Dean played the villain in this film, Trevor Gooden. After cheating on his wife, Kristy, he conspires to kill her. Trevor and his friend plan to use the Lament Configuration, but the plan backfires when Kristy shoots him instead.

Gooden being shot causes a car accident, and when he awakes from the accident Gooden finds himself in Hell with no memory of what transpired previously. 

John Wick (2014)

In the 2014 neo-noir action thriller film, Winters plays another villian. His character, Avi, is an advisor to a crime lord, Viggo Tarasov, and his second in command.

When Tarasov's son runs afoul of John Wick by stealing his car and killing his dog, Wick takes revenge on the son. Avi is caught up in the action and ends up being killed by Wick.

Don Peyote (2014)

In 2014, the same year John Wick was released, Winters played a gun dealer in Don Peyote. It is a minor role in a film about a unemployed, marijuana smoking slacker who has a spiritual awakening after meeting a homeless man and becomes obsessed with doomsday and conspiracy theories. 

Palmer (2021)

More recently, Winters played Jerry, an abusive boyfriend. When Eddie Palmer is released from prison after 12 years for attempted murder, he befriends Jerry's girlfriend's son, a bullied boy named Sam. The film was directed by Fisher Stevens and stars Justin Timberlake as Palmer.


Starting in 2017, Winters began playing a personified version of Mayhem in Allstate commercials.

While driving a pink van and wearing pink glasses, so as to resemble a teenage girl, he becomes emotionally distracted behind the wheel and causes an accident. As the other driver checks her car, Mayhem drives off, showing the need for good auto insurance.

The following year, another Allstate commercial staring Mayhem aired. In this version, Mayhem performed a goofy dance as part of a social media challenge. He distracted a driver, who subsequently crashed his car.

Winters was reported to receive $4,000,000 for the first commercial and $1,000,000 for the second.

Rites & Wrongs

A new film, Rites & Wrongs, is currently in pre-production. Winters will play Gianni in the film.

Real estate

Winters currently lives in New York City. In 2018, he purchased a $3,500,000 duplex loft in the Tribeca neighborhood.

The five-story unit has two bedrooms, two bathrooms, and an outdoor space totaling 1,800 square feet. It also features a room that resembles a bowling alley accessible by a lock key elevator. 

The main living space has a corkscrew staircase that leads to a glass walled den. The den has a vaulted ceiling and glass doors that open to the north and the south.

Through the north door is a small terrace and, to the south, there is a view of One World Trade Center.

Winters' net worth

With his acting jobs, both on TV, movies, and commercials, Winters has earned quite a bit of money. He is reported to have a net worth of $6 million.

If you would like to know more, additional details about his life and career can be found on either his IMDB page or his Wikipedia article

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Allen Lee

Written by Allen Lee

Allen Lee is a Toronto-based freelance writer who studied business in school but has since turned to other pursuits. He spends more time than is perhaps wise with his eyes fixed on a screen either reading history books, keeping up with international news, or playing the latest releases on the Steam platform, which serve as the subject matter for much of his writing output. Currently, Lee is practicing the smidgen of Chinese that he picked up while visiting the Chinese mainland in hopes of someday being able to read certain historical texts in their original language.

Read more posts by Allen Lee

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