OutKick
  • Sports
  • Culture
  • Analysis
  • Watch
  • Shows
  • Shop
  • Newsletters
  • Search

Jay Cutler

NBA Coach Making a Romantic Play for Kristin Cavallari

Alejandro Avila
November 18, 2025
Jay Cutler at a Chicago Bears game

Jay Cutler To Spend Opening Weekend Of College Football Behind Bars After DUI Arrest

Mark Harris
August 27, 2025

Kristin Cavallari's Nasty Divorce Claim Triggers A Response From Jay Cutler: 'Borderline Slander'

Joe Kinsey
August 20, 2025

Kristin Cavallari's Nasty Divorce Claim Triggers A Response From Jay Cutler: 'Borderline Slander'

Joe Kinsey
August 20, 2025

Jay Cutler Triggers The Libs By Killing An Animal In Africa: 'Small D--k Energy'

Joe Kinsey
July 14, 2025
Former NFL QB Jay Cutler was arrested in Tennessee on charges of DUI, failure to exercise due care, violation of implied consent law, and possession of a handgun while under the influence. (Credit: Getty Images)

Jay Cutler Arrested In Tennessee On Multiple Charges: DETAILS

David Hookstead
October 18, 2024

Jay Cutler Triggers The Libs By Killing An Animal In Africa: 'Small D--k Energy'

Joe Kinsey
July 14, 2025
Former NFL QB Jay Cutler was arrested in Tennessee on charges of DUI, failure to exercise due care, violation of implied consent law, and possession of a handgun while under the influence. (Credit: Getty Images)

Jay Cutler Arrested In Tennessee On Multiple Charges: DETAILS

David Hookstead
October 18, 2024
Kristin Cavallari admits she just wants to have fun at the ripe old age of 37.

Kristin Cavallari's New 'Best Sex' Claim Is A Huge Shot At Jay Cutler

Joe Kinsey
September 3, 2024
Jay Cutler pulled off an awesome move for wives of Navy SEALs who paid the ultimate price. He took them hunting. (Credit: Getty Images)

Jay Cutler Pulls Classy Move For Wives Of Fallen Navy SEALs, Proves He's An American Patriot

David Hookstead
January 12, 2024
Jay Cutler and new girlfriend Samantha Robertson make debut.

Jay Cutler Back From The Dead With A New Girlfriend And She's A Rocket

Zach Dean
October 6, 2023
Jay Cutler's journey to Vanderbilt was pretty unorthodox. Coaches at first thought he was a tight end. (Credit: Getty Images)

Jay Cutler's Vanderbilt Recruitment Story Is Hilarious, Coaches Thought He Was A TE

David Hookstead
June 6, 2023

Jay Cutler Bags Massive Bear On Successful Hunting Trip

David Hookstead
June 1, 2023
Jay Cutler Selling Tennessee Home, Previously Shared With Ex-Wife Kristin Cavallari

Jay Cutler Selling Tennessee Home, Previously Shared With Ex-Wife Kristin Cavallari

Amber Harding
March 11, 2023
Kristin Cavallari dated Matt Leinart before marrying Jay Cutler.

Kristin Cavallari Admits She Dated Matt Leinart Before Jay Cutler, Says She's Done With Athletes

Zach Dean
January 18, 2023
Tim Tebow and Jay Cutler go together great!

Jay Cutler Mistaken For Tim Tebow In Terrible Jeopardy! Answer

Zach Dean
November 16, 2022
OutKick
  • Sports
  • Culture
  • Analysis
  • Watch
  • Shows
  • Newsletters
  • Shop
  • Updated Terms of Use
  • Updated Privacy Policy
  • Your Privacy Choices
  • Help
  • About Us
  • Press
  • Sitemap

DISCLAIMER: This site is 100% for entertainment purposes only and does not involve real money betting. Gambling related content is not intended for anyone under the age of 21. If you or someone you know has a gambling problem and wants help, call 1-800-GAMBLER.