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On September 9, 2018, Monson was elected to the City's Duma (local city parliament) of Krasnogorsk, a city located near Moscow.

In April 2016, Monson expressed his desire to join the Communist Party of the Russian Federation in a video appeal to the party and praised socialism as "the only way as a human species that we’re going to survive." Soon after, he was invited to meet Communist Party of the Russian Federation leader Gennady Zyuganov in his office in the State Duma, where they discussed the future of communism in Russia and globally. Monson later led a procession across Red Square into Lenin's Mausoleum together with Zyuganov dedicated to the anniversary of Vladimir Lenin's birth. He was appointed as a special representative for international cooperation by the Communist Party of the Russian Federation's Sport Club in June 2016.

Monson was the subject of a party political advertisement released in the run-up to the 2016 State Duma Elections.

On September 11, 2016, Monson announced on Twitter that he had become a citizen of the Luhansk People's Republic to support local people who suffered in the War in Ukraine. He was made an honorary citizen of the Republic of Abkhazia in October 2016 for "supporting nations striving for self-determination."

In 2015, Monson sought Russian citizenship, citing that he felt "Russian in spirit." He was granted Russian citizenship in 2018 by President Vladimir Putin.

From June 2013 to April 2014, Monson would go 1–6 in seven fights, defeating Denis Komkin, and losing to notable fighters such as Alexey Oleynik, Satoshi Ishii, and Mike Hayes. After a loss to up-and-comer Chaban Ka, Monson defeated Kevin Brooks via north-south choke at Fight Time 20 on August 29, 2014.

Monson faced Dmitry Titkov on September 5, 2014, at Fight Star: Saransk vs. Penza. He lost the fight by cut TKO, after a cut opened up on Monson.

At UFC 57, Monson submitted Branden Lee Hinkle by north–south choke in the first round. At UFC 59, he fought Brazilian jiu-jitsu black belt Marcio Cruz (ADCC veteran and longtime rival). Monson won by decision after three rounds. At UFC 61, Monson fought another Brazilian jiu-jitsu black belt in Anthony Perosh, whom Monson defeated by TKO in the first round.

His next fight was scheduled to be against Neil Wain at "KnuckleUp: Kings of the North," but Neil Wain pulled out of the fight due to injuries. Stepping in to replace Wain was the very man who took him out of the fight, Dave Keeley. Monson defeated Keeley by submission (north–south choke) in the first round.

Monson was unbeaten in his four fights after the loss against Fedor, and in June 2012 signed a four-fight deal with the Super Fight League in India. Monson was originally announced to fight at SFL 4 on September 29 against former UFC fighter Todd Duffee but after the event was pushed back twice the SFL decided to change the structure of their shows, with weekly events replacing monthly events. Duffee and SFL agreed on his departure in September and he is currently fighting in the UFC. Following this news, the fight was canceled.

In 2011, Monson defeated Lee Mein on January 7 and Tony Lopez on April 1 in a five-round decision.

Monson defeated Paul Taylor in Birmingham, England at the Sprawl n Brawl promotion on October 9, 2011.

Monson fought Fedor Emelianenko at M-1 Global: Fedor vs. Monson on November 20, 2011 in Moscow, Russia and lost by unanimous decision.

At 5150 Combat League/Xtreme Fighting League: New Years Revolution, Monson defeated John Brown by split decision on January 16, 2010.

On March 13, 2010, Monson fought in France at 100% Fight II and defeated Francisco Nonato by submission (guillotine choke) in the first round. He lost to Travis Wiuff in a split decision at XKL Evolution 2 on April 24, 2010. On May 14, 2010, he lost in Abu Dhabi to Shamil Abdurahimov by majority decision at the Abu Dhabi Fighting Championship in the Quarter Finals of the 2010 Openweight Grand Prix.

Monson defeated Bira Lima at Impact FC 1 in Australia on July 10, 2010, by unanimous decision.

Monson faced Jason Guida on August 21, 2010, at an event called "Fight Time 1". He defeated Jason Guida at 3:04 in the second round by a guillotine choke submission.

On March 21, 2009, Monson won a controversial decision against Roy Nelson on Roy Jones Jr.'s hybrid boxing/MMA card "March Badness." He then beat Sergej Maslobojev on a Cage Wars card on March 29, 2009. He immediately went to Japan and defeated top Russian Heavyweight Sergei Kharitonov on April 5, 2009, at Dream 8, giving him three wins in two weeks.

On September 12, 2009, at Bitetti Combat MMA 4, Monson had his seven-fight win streak snapped, losing in a rematch with Pedro Rizzo by unanimous decision.

On January 14, 2009, Monson was charged with First Degree Malicious Mischief for vandalizing the Washington State Capitol by spray-painting "an anarchy symbol, a peace symbol and the words 'no poverty' and 'no war'" on the large columns at the front of the building.

On July 29, 2009, Monson pleaded guilty to malicious mischief and entered an Alford plea for graffiti.

In October 2009, he was sentenced to 90 days of work release and ordered to pay $21,894 in restitution. The fine has since accrued interest and now amounts to $24,749.80. As of January 2011, he had only paid $421 of his court-ordered restitution.

Monson defeated former UFC Heavyweight Champion Ricco Rodriguez in the main event of the Mixed Fighting Alliance "There Will Be Blood" event on December 13, 2008. He avenged a loss to Rodriguez from almost seven years prior.

At the main event of PRIDE 34, on April 8, 2007, Monson defeated Kazuyuki Fujita via rear-naked choke submission at 6:37 of the opening round.

His next fight was scheduled to be against Chris Guillen on August 17, 2007, for the Global Fighting Championships' Heavyweight Championship, but the event was canceled after four of the eight scheduled bouts were removed from the card. Monson lost against Pedro Rizzo at Art of War 3, which was held on September 1, 2007. During the bout, Monson displayed a much improved level of striking, and kept the fight standing virtually the entire time.

On September 7, 2007, Monson won a total of two matches in the FILA World Championship in Turkey, defeating France's Zoro Piere and England's Tom Blackledge by submission. Monson was awarded the 275-pound gold medal when his final opponent Ramon Diaz suffered an injury and was forced to bow out.

On November 18, 2006, at UFC 65, Monson fought Tim Sylvia for the UFC Heavyweight Championship. He lost a five-round decision and would later ask to be released from his UFC contract in the hopes of facing then-PRIDE Heavyweight Champion Fedor Emelianenko at a BodogFIGHT scheduled for March 2007. However, negotiations fell through and the match did not happen during that time.

Monson is considered to be one of the world's top submission grapplers. He is a multiple event winner at NAGA, Grapplers Quest and FILA, among other submission tournaments. He is nicknamed "The Snowman" for his performance at the 1999 Abu Dhabi Combat Club Submission Wrestling World Championship. The Brazilian fighters at the tournament gave him the nickname because he came in as an unknown, but beat four Brazilians in a row to win the 88–98 kilogram weight class. As he went along in the tournament and continued to beat his opponents, they said he was like a snowball (white, compact, rolling and getting bigger and stronger as the tournament went on).

Jeffrey William Monson (born January 18, 1971) is an American-Russian mixed martial artist currently competing in the Heavyweight division. A professional competitor since 1997, he has competed for the UFC, Strikeforce, DREAM, PRIDE, M-1 Global, Impact FC, World Victory Road, and Cage Warriors. In Brazilian jiu-jitsu and grappling, Monson is a two-time winner of the ADCC Submission Wrestling World Championship, and a No Gi Brazilian jiu-jitsu World Champion. Monson is an anarcho-communist known for his radical left-wing political views. He is the host of Monson TV on RT.