PokerBoom revisited one of poker's legends of the past – Shahram "Shawn" Sheikhan. You may recognize him from YouTube, often clashing with Mike Matusow. Along with his poker career, Shawn's life had some twists and turns that you might not have heard about.

This is Shawn Sheikhan at the peak of his career.

And this is Shawn Sheikhan now.

So, the question is, how could you go from winning millions to potentially facing decades in prison? Let's find out.

Who is Shawn Sheikhan?

Poker is a game of skill, strategy, and sometimes unpredictable twists of fate. In the world of professional poker, few figures have captured the attention of enthusiasts and fans quite like Shawn Sheikhan.

Born Shawn Sheikhan on December 29th, 1969, Sheikhan grew up in Iran in the midst of political turmoil. Raised in a country undergoing a revolution, Shawn's early years were marked by upheaval. As a young boy, he experienced firsthand the hardships that came with being a religious minority in a changing nation.

At the age of 13, he and his family immigrated to the United States in search of a better life. Settling in Southern California, they began the process of adapting to a new culture and a new language.

Shawn's introduction to poker came during his time in California, where he quickly became enamored with the game. He began playing in home games in local card rooms, developing his skills and refining his poker strategy.

Poker With Friends For Free Or With Real Money

His poker skills became evident when he entered the professional poker circuit. Throughout his career, he achieved several significant victories and garnered attention for his bold and aggressive playing style.

One of his most notable accomplishments was in July 2007 when he placed third in the World Series of Poker No Limit Duece to Seven Lowball event. His fearless approach to the game, characterized by his willingness to take risks and put his opponents to the test, made him a memorable figure in the poker world.

But Shawn's notoriety in poker extends beyond his playing skills. It's also marked by his often questionable table etiquette.

Probably one of the most memorable instances of this came during the 2005 World Series of Poker, where he engaged in a widely publicized verbal clash with fellow player Mike "The Mouth" Matusow.

The source of this confrontation was Shawn's impulsive reaction when a flop was revealed in the hand he wasn't even participating in. He slammed the table in frustration, inadvertently giving away the strength of his hand.

This led to both Matusow and Sheikhan receiving penalties.

Matusow responded by swearing at him after Shawn's outburst. "You know, we're in a hand. You need to shut the f*** up."

Shawn's contentious interactions at the poker table don't stop there. Another notable incident occurred during a game of Poker After Dark, where he found himself in a dispute with Phil Hellmuth.

"Shawn, would you please mind this time? Please, please be quiet. Please be quiet so I can talk."

Hellmuth accused Sheikhan of incessantly talking while he was involved in the hand with Annie Duke, even though the entire table was also engaged in conversation.

Despite his occasional controversial behavior, Sheikhan demonstrated his poker skills on numerous occasions.

In March 2006, he secured a spot in the final four of NBC's National Heads-Up Poker Championship, an impressive feat in a prestigious tournament. During the early rounds of this championship, he even had the audacity to tell Gus Hansen, whom he eventually would eliminate, to discard his cards, all while holding four of a kind.

His deep run in the tournament earned him a substantial $125,000 prize, although he ultimately fell short, losing to the eventual champion, Ted Forrest. Well, Shawn Sheikhan isn't the first opponent to be thwarted by Ted Forrest's spooky heads-up luck.

Legal Troubles in California

In recent years, Shawn Sheikhan's life took a dramatic turn when he became embroiled in legal troubles related to his involvement in the cannabis industry.

In 2021, Sheikhan was arrested and faced multiple charges, including conspiracy to distribute marijuana and operating an unlicensed money transmitting business. These charges carried the potential for a lengthy prison sentence and a substantial fine. On June 30th, 2022, Shawn Sheikhan entered a guilty plea in the United States District Court, Southern District of California, admitting to his involvement in the illicit cannabis enterprise.

A DOJ press release about Shawn's case and others

Seeking to sway the judge, Shawn's legal counsel submitted a sentencing memorandum to the court with the hope of persuading the judge to consider probation as an alternative to incarceration. Contained within a comprehensive 33-page document obtained by Poker News, the defense outlined various grounds for leniency. Notably, a number of individuals closely associated with the poker pro, including PokerGo president Mori Eskandani, provided letters of support on Shawn's behalf.

The memorandum highlighted Eskandani's professional involvement with Sheikhan, having invited him to participate in multiple poker shows produced over the years.

In their arguments, Shawn's legal reps contend that a downward variance in sentencing is warranted. Essentially, they proposed that the court should impose a less severe punishment than the standard sentencing guidelines typically applied to the type of offense he admitted to committing.

The defense's case for a downward variance hinges on several factors outlined in the memorandum, including Shawn's remorse for his actions, his acknowledgment of guilt, the support he has received from figures like Eskandani, and the evolving landscape of marijuana laws.

The defense underscores Shawn's acknowledgment of responsibility and genuine remorse, as he has willingly accepted his mistakes without any intention of avoiding accountability. Furthermore, the legal team argues that probation would serve as an effective deterrent against future criminal activities, as Sheikhan does not pose a threat to public safety. The memorandum also highlights Shawn's health concerns, including degenerative disc disease, emphasizing that these factors do not support a prison sentence.

Additionally, Sheikhan voluntarily forfeited $191,000 in cash and property that now rests in the government's possession. The defense requests that the court consider this forfeiture as an additional form of punishment when determining the appropriate sentence. The proposed probationary sentence would incorporate components such as home detention, mandatory drug testing, community service, and counseling. The document closes by emphasizing Shawn's acknowledgment of his conduct in the case, expressing sincere remorse, and emphasizing full compliance with pre-trial conditions with a firm commitment to abstain from any future involvement in criminal activities.

However, this is not Shawn's first brush with the law. He was arrested in 2007 due to a 1995 conviction for misdemeanor sexual battery on a child under 18, where he served 9 months in prison and 5 years of probation. According to Shawn's lawyer, the young woman in the case was a 17-year-old girl that Sheikhan knew when he was in his early 20s.

Needless to say, Shawn's life and career have been a roller coaster ride, marked by highs and lows. From his prominence in the poker world to his current legal battles, his story is a testament to the unpredictability of life's journey. Shawn Sheikhan's story is a reminder that success is not linear, and it comes with many twists and turns and failures. It remains to be seen where his journey will ultimately end.

According to reports, Shawn has to surrender himself on January 1st, 2024 by noon. His release is scheduled for 2028.

The maximum sentence for his charges was forty years in prison, though he managed to get a significant reduction.