Early Life and Education of Jay Cutler: A Complete Timeline

By Popular Timelines Editorial Team · Updated: October 4, 2025

How education and upbringing influenced the life of Jay Cutler. A timeline of key moments.

Jay Cutler is a retired American football quarterback who played 12 seasons in the NFL. He is best known for his time with the Chicago Bears, where he holds the franchise records for passing yards, touchdowns, attempts, and completions. Cutler also played for the Denver Broncos and briefly for the Miami Dolphins before retiring from professional football.

Sections (4)

Full Timeline Early Life & Education Career & Achievements Success & Recognition

1967: Last Commodore to win SEC Offensive Player of the Year before Cutler

In 1967, before Jay Cutler won the award in 2005, it marked the last time a Vanderbilt Commodore had been named SEC Offensive Player of the Year.

April 29, 1983: Jay Cutler's Birth

On April 29, 1983, Jay Christopher Cutler was born. He would later become a professional football quarterback in the National Football League (NFL).

1983: Cutler's Birth in Santa Claus, Indiana

In 1983, Jay Cutler was born in Santa Claus, Indiana. He later attended Heritage Hills High School.

2001: Redshirted Freshman Season

In 2001, Jay Cutler redshirted during his freshman season at Vanderbilt University.

2002: Set School Records as Freshman

In 2002, Jay Cutler set school records for touchdowns and rushing yards by a freshman at Vanderbilt, and he rushed for more yards than any other Southeastern Conference quarterback that year.

2004: Record Completion Percentage

In 2004, as a junior, Jay Cutler completed 61.0 percent of his passes, setting a school record, while throwing for 1,844 yards with 10 touchdowns and a career-low five interceptions.

2005: Graduation from Vanderbilt

In 2005, Jay Cutler graduated from Vanderbilt with a bachelor's degree in human and organizational development.

2005: SEC Offensive Player of the Year

In 2005, Jay Cutler was named SEC Offensive Player of the Year as a senior at Vanderbilt, becoming the first Commodore to win the award since 1967.

2007: Jay Cutler Foundation started

During the 2007 offseason, Jay Cutler started the Jay Cutler Foundation to help at-risk youth.

2007: Filming Oprah's Big Give

In 2007, Jay Cutler participated in an episode of Oprah's Big Give filmed in Denver.

March 9, 2008: Oprah's Big Give episode airs

On March 9, 2008, the episode of Oprah's Big Give featuring Jay Cutler aired on ABC.

May 1, 2008: Cutler diagnosed with diabetes

On May 1, 2008, Jay Cutler announced that he had been diagnosed with type 1 diabetes.

2009: "Touchdowns For Diabetes" campaign

In 2009, Jay Cutler teamed up with Eli Lilly and Company in a campaign called "Touchdowns For Diabetes" to support diabetes camp scholarships.

September 2010: Cutler starts dating Cavallari

In September 2010, Jay Cutler began dating Kristin Cavallari.

April 2011: Engagement to Cavallari

In April 2011, Jay Cutler and Kristin Cavallari got engaged.

July 2011: Engagement called off

In July 2011, Jay Cutler and Kristin Cavallari called off their engagement.

2011: "Cutty Come Back" parody song

In 2011, after the Bears lost games due to Cutler's thumb injury, Magic 1 released "Cutty Come Back", a parody of "Baby Come Back".

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2012: Supports Mitt Romney

In 2012, Jay Cutler supported Mitt Romney in the United States presidential election.

2012: Diabetes Awareness visit

In 2012, Jay Cutler visited Perspectives Charter School in Chicago to discuss diabetes awareness.

June 7, 2013: Cutler marries Cavallari

On June 7, 2013, Jay Cutler and Kristin Cavallari were married in Nashville, Tennessee.

2013: Cutler appears on "The League"

In 2013, Jay Cutler played himself in an episode of the comedy show "The League" alongside his ex-wife, Kristin Cavallari.

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2014: Rodgers references the meme

In 2014, Aaron Rodgers of the Green Bay Packers referenced the "Smokin' Jay Cutler" meme during a game against the Bears.

2016: Supports Donald Trump

In 2016, Jay Cutler supported Donald Trump in the United States presidential election.

2016: Inducted into Vanderbilt Athletics Hall of Fame

In 2016, Jay Cutler was inducted into the Vanderbilt Athletics Hall of Fame, recognizing his achievements and contributions to the university's sports program.

2018: Appears on Very Cavallari

From 2018, Jay Cutler made regular appearances on the show Very Cavallari.

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April 2020: Divorce announcement

In April 2020, Jay Cutler and Kristin Cavallari announced that they were getting a divorce, citing that they had "grown apart".

2020: Questioning election results

Following the 2020 election, Jay Cutler created and then deleted a post on his Instagram account questioning Joe Biden's victory.

2020: Supports Donald Trump

In 2020, Jay Cutler supported Donald Trump in the United States presidential election.

2020: Appears on Very Cavallari

Until 2020, Jay Cutler made regular appearances on the show Very Cavallari.

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May 2021: Divorce not finalized

In May 2021, Jay Cutler and Kristin Cavallari had not yet finalized their divorce due to financial issues.

2021: CUTS meat subscription and Uncut podcast launched

In 2021, Jay Cutler launched a meat subscription service called CUTS and his podcast "Uncut".

June 2022: Divorce finalized

In June 2022, it was reported that Jay Cutler and Kristin Cavallari's settlement had been finalized and the couple was officially divorced.

2022: Gratis Brewing and Outsider.com

In 2022, Jay Cutler launched Gratis Brewing, based in Nashville. He also became a founding partner in Outsider.com, a digital media lifestyle company.

2023: Cutler dates Robertson

In 2023, Jay Cutler revealed on Instagram that he was dating Samantha Robertson.

October 17, 2024: Cutler arrested for DUI

On October 17, 2024, Jay Cutler was arrested in Franklin, Tennessee, on suspicion of driving while intoxicated and possessing a firearm while under the influence. He was charged with DUI-first offense, possession of a handgun-under the influence, failure to exercise due care to avoid a collision and implied consent.

2024: Cutler and Robertson get engaged

In 2024, People reported that Jay Cutler and Samantha Robertson were engaged.

August 26, 2025: Cutler Sentenced to Jail for DUI

On August 26, 2025, Jay Cutler was sentenced to four days in jail as part of a plea deal where he pled guilty to driving under the influence. As part of the agreement, a weapons possession charge was dismissed, and he was ordered to surrender a pistol found in his car, pay a $350 fine, attend a DUI safety class, and was placed on unsupervised probation for one year. His Tennessee driver's license was also revoked.