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Before Chicago Bears Quarterback Jay Cutler Pro Football last played in 2017, but the Pro Bowler has not stayed out of the apparent after retirement.
From his high profile marriage to Kristin Cavallari To his DUI 2024 arrest, Cutler is one of a handful of athletes who have become the name of a home beyond the NFL.
Cutler and Cavallari began dating in 2010, early in his bears career, and participated in 2011.
“Jay is a good Midwestern boy; he’s a gentleman,” Cavallari told only Weekly US before their engagement. “It opens car doors and made the laundry today, which, in my opinion, is pretty cool, so it’s a good boy. We’re in love!”
Kristin Cavallari and Jay Cutler’s relationship had his share of unusual things before eventually ending in April 2020. “Jay is a good Midwestern boy; he’s a gentleman,” Cavallari told (…)
The pair split three months later but eventually were reconciled and were married in 2013. The a couple sharing three childrenThe sons of Camden and Jaxon, as well as the daughter of Saylor.
Cutler and Cavallari separated for good in 2020 and complete their divorce Two years later, with the former -QB now engaged Samantha Robertson.
Keep scrolling for the progress and decline of Cutler over the years.
2006
Jay Cutler in the NFL Scout Combination
Photo by Jim Rogash/Getty ImagesAs an offensive player of the reign, Cutler was generally drafted 11th out of Vanderbilt by the Denver Broncos in the 2006 NFL draft draft. He signed with the team on a six -year contract, $ 48 million in motivation.
Jay Cutler off the market! After over a year of dating, the famous former quarter has now engaged to Samantha Robertson. Cutler, 41, is best known for his time at the NFL, playing as a quarter of the Denver Broncos, Chicago Bears, and Miami Dolphins. Previously, Cutler was married to Laguna Beach star Kristin Cavallari. (…)
May 2008
After losing 35 pounds of the previous season and saying he had “no energy,” Cutler learned that he had type 1 diabetes. While he insisted his football career was not at stake, he said he needed daily insulin shots.
“We thought it might be stressful and grinding going through a whole season,” he told Nfl.com at the time. “But once I got back here and started working out again, I didn’t make any improvement. I didn’t strengthen anything. I was still losing weight.”
The fall of 2008
Pro Bowl Lone Cutler season came the same year with his diagnosis. Also his final season with the Broncos, he threw for 25 touches, setting franchise records for passing yards, completion and efforts. He was traded to the bears after the season.
Kristin Cavallari made waves on Laguna beach in the early 2000s, and has been entertaining us ever since. Cavallari made his reality television appearance in 2004 on term 1 of Laguna beach. He returned for season 2 and later became the pot on the hills following Lauren Conrad’s departure. After finding love with former NFL (…)
April 2011
Kristin Cavallari and Jay Cutler
Photo by Timothy Hiatt/Getty ImagesCutler offered Cavallari over the Easter weekend 2011, with a source saying Us At the time the alum of the Hills was “so excited and completely blind.”
July 2011
They both broke their engagement after only three months. Cutler confirmed their short -lived partition via Facebook, writing, “Thank you all for the support, but if you talk badly about Kristin I will delete you and block you.” They reconciled and were engaged again in November.
2012
Cutler and Cavallari welcomed their first child, his son Camden.
Jay Cutler credits his children for making his goparenting relationship with Kristin Cavallari’s work. “The children do that,” Cutler, 42, shared only us Weekly in The Folds of Honor Tennessee Rock ‘n jock Ball Game Jock celebrities on Monday, June 2. ” We have our schedule and it works for us. ”Cutler and (…)
2013
Cutler and Cavallari tied the knot at the County Clerk’s office in Nashville, Tennessee, celebrating with a church ceremony the following day.
2014
The former couple welcomed the son of Jaxon.
2015
Kristin Cavallari and his daughter Saylor
Courtesy of Kristin Cavallari/InstagramCutler and Cavallari announced the birth of their third child, daughter of Saylor.
Jay Cutler has officially entered the age of his girlfriend with Samantha Robertson. A former NFL star launched his relationship hard through social media in September 2023, years after his divorce from Kristin Cavallari. Cutler and Cavallari were together for 10 years before the announcement of their division in 2020. They share three children. Although Neither Cutler nor Robertson (…)
2020
The pair announced their divorce in a joint statement.
“We have nothing but love and respect for each other and we are very grateful for the shared years, memories made and the children we are so proud of,” they said. “This is the position of two people growing apart.”
Cavallari later noted “inappropriate marital behavior” by Cutler and “incompatible differences” as reasons for their division.
They completed their divorce in 2022.
2021
Cutler claimed that Uber Eats was dropped from an advertising opportunity after he spoke against Covid-19 regulations in the school area of his Tennessee town. He added that his “scenes do not align” with the company.
“Lost an ad with Uber Eats partnering with the NFL,” he wrote through X at the time. “Going to film in LA, ‘scenes are not aligned.’ Guess that they do not like school board members in the future.
2024
After becoming an Instagram officer in September 2023, Cutler and his girlfriend Samantha Robertson announced their engagement just over a year later.
2025
Jay Cutler
Photo from Franklin Police Department via Getty ImagesCutler was arrested in Franklin, Tennessee on charges of driving while intoxicating and possession of guns while under the influence, after officers responded to an accident involving two vehicles. He refused to take the test of a field sobriety, while authorities found a rifle and hand gun in his car, according to the arrest report.
Later hit a plea deal with prosecutors He pleaded guilty to one account of DUI misconduct. In August 2025, he was sentenced to four days in prison and a $ 350 fine. He also agreed to attend DUI classes and revoke his license for a period of time. He will serve a year of trial after his release.
