Who Has Bill Simmons Dated? Exploring His Relationship Timeline and Partners

Bill Simmons is not only known for his illustrious career in sports media but also for his personal life. Apart from being an American sports journalist, podcaster, and sportswriter, he is the proud founder and CEO of the popular sports website, The Ringer

Born on September 25, 1969, in Marlborough, Massachusetts, Simmons rose to prominence as "The Boston Sports Guy," impressing fans and fellow sports enthusiasts with his astute insights. Beyond his professional achievements, he has found happiness in his personal life, as he is married to Kari Simmons. Together, they share their lives and continue to support each other in their respective endeavors. 

Married To Kari Simmons

Bill Simmons and Kari Simmons have shared a strong bond since they got married in 1999. They lead a private life and prefer to keep their relationship away from the public eye. While he is well-known for his work in the sports media industry, he hasn't disclosed many details about his marriage to Kari. 

Bill Simmons with Ben Affleck and Matt Damon SOURCE: Bill Simmons Instagram @billsimmons

Despite the spotlight on his professional life, Simmons values the privacy of their relationship and chooses to keep their matters private. Living a quiet and happy married life, the couple enjoys their time together, away from the hustle and bustle of the public spotlight. Their commitment to each other and their shared love for privacy have allowed them to nurture a lasting and meaningful relationship throughout the years. 

About His Wife Kari Simmons?

Kari Simmons, also known by her real name Kari Crichton, is someone who cherishes her privacy and keeps a low profile. She gained fame under the pseudonym "The Sports Gal" and is recognized for her contributions to the sports world. She attended St. Bonaventure University, where she graduated in 1994. 

Despite her public presence as "The Sports Gal," Kari has chosen not to disclose much about her personal life. Tragically, she experienced the loss of her brother, Jim, who passed away on March 26, 2011, at the age of 49 as mentioned on the Doyle Funeral Home website. Her parents, James Crichton, Sr., and Sandra Crichton have been a significant source of support in her life. 

Kari also has another brother named Joseph Crichton, who shares a close bond with her. Through all the ups and downs, she remains a private individual, focusing on her passions and continuing to make her mark in the sports world. Her commitment to her work and her family has been evident, and her resilience in the face of loss is a testament to her strength. Despite her fame, she continues to lead a private life, which has garnered respect and admiration from her fans.

Has Two Kids With His Wife, Kari

Bill Simmons and his wife, Kari have been blessed with two children, a son, and a daughter. Their daughter, Zoe Simmons, was born in 2005, while their son, Benjamin Oakley Simmons, arrived in 2007. Benjamin prefers to live a low-key life, staying away from the limelight and public attention that comes with his father's fame. 

Bill Simmons and son, Benjamin Oakley Simmons at the NBA game SOURCE: Bill Simmons Instagram @billsimmons

Zoe and Benjamin, both of them are very athletic and enjoy playing sports. She is a talented soccer player and currently serves as a senior forward on the Emerson College Women's Soccer team. She made an impressive start to her college soccer career, being named Rookie of the Year and earning a spot on the 1st-team All-League during her freshman year. As she progressed, she continued to excel, becoming the team's MVP and again achieving 1st-team All-League honors in her senior year while playing for Crossroad Athletics.

On the other hand, Benjamin is actively involved in lacrosse and represents Harvard-Westlake Lacrosse. Apart from lacrosse, he has a strong passion for WWE (World Wrestling Entertainment). Interestingly, his love for WWE has created a special bond between him and his father Simmons, as they both enjoy watching and discussing Wrestlemania together.

The Picking Football Games Between Simmons And His Wife

The tradition of picking football games between Bill Simmons and his wife, Kari Simmons, began in the lead-up to the 2006 season. Curious to know if there was any logic or strategy behind making these predictions, Bill posed a thought-provoking question he could, with all his knowledge of sports, pick games better than someone who didn't have that expertise. 

To find out, Simmons decided to include his wife, Kari known as the Sports Gal, in the fun. She eagerly accepted the challenge, but she had one condition: she wanted a space in each column to freely express her thoughts and rant about any subject of her choice. He agreed, and the friendly competition commenced. As the season unfolded, her rants found a place in the columns. 

It turned out that Kari's intuitive picks and perhaps a touch of luck led to her outperforming her sports-savvy husband in the game-picking contest. Her victory not only showcased her knack for football predictions but also her distinct voice and opinions, which added an engaging and entertaining element to the columns. 

Simmons Marriage And Divorce With The ESPN

The relationship between Bill Simmons and ESPN has been widely discussed in public, often referred to as the "Simmons and ESPN marriage." It all began in 2001 when he received a job offer from ESPN, catapulting him into the spotlight as a sports journalist. Known for his bold and provocative writing style, he quickly gained a devoted following. 

However, despite the initial success and fruitful collaborations, Simons and ESPN's partnership has been characterized as a "troubled marriage," marked by conflicts and disagreements along the way. The two have found themselves in a few battles over various issues, leading to tensions and occasional public spats. The relationship between the two has faced its fair share of challenges over the years. 

One of the earliest notable issues arose in 2008 when ESPN canceled a scheduled BS Report episode between Simmons and then-presidential candidate Barack Obama, which disappointed many fans who were eager to hear their conversation. In March 2013, he found himself in hot water when he was suspended by the network for openly criticizing the network's show, First Take

Another significant point of contention arose in March 2015 when there seemed to be a lack of support for Simmons' beloved creation, Grantland, an innovative sports and pop culture website. This lack of backing from the network left the website's future uncertain. Then, in May 2015, he once again found himself in trouble after making critical remarks about NFL Commissioner Roger Goodell on The Dan Patrick Show, sparking further tensions with ESPN and adding to the strain on their relationship. 

The strained relationship between Simmons and ESPN eventually led to a significant split. In May 2015, the situation reached its breaking point when he was fired from ESPN. The decision came from the network's president at the time, John Skipper, who publicly stated that the reason for his termination was due to a "repeated lack of respect," he has shown towards them as mentioned in an article from The Hollywood Reporter.


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