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Bears Legend Wins $50 Million Divorce Court Battle After Ex-Wife Tried to Seize Majority of Assets

Chicago Bears Cut Jay Cutler After One Playoff Appearance in Eight Years -  The New York Times

Chicago, IL – October 1, 2025
Another NFL legend just put points on the board — not on the field, but in the courtroom. Jay Cutler, the iconic former Chicago Bears quarterback who led the team to an NFC Championship appearance, has won a bitter divorce battle with his ex-wife.

Cutler, who earned roughly $100 million in NFL salary and bonuses from 2006–2017, has grown his wealth to over $70 million through TV contracts, endorsements, and investments. But that fortune was seriously threatened.

Court filings reveal that Cutler’s ex-wife, Kristin Cavallari — the reality TV star he married in 2013 — sought more than 70% of the marital estate, estimated at about $50 million. She also requested monthly support exceeding $100,000, alleging infidelity and family neglect after Cutler’s retirement.

However, Cutler’s legal team uncovered forensic evidence showing Cavallari transferred nearly $4 million from joint accounts to shell companies registered under relatives’ names. Additional large expenses — luxury travel, jewelry, and private events — were paid without Cutler’s consent.

Illinois State Court Judge William R. Matthews issued a decisive ruling in Cutler’s favor, finding that Cavallari had “intentionally concealed and dissipated marital assets.” The decision awards Cutler 50% of the marital property — roughly $25 million — and orders Cavallari to return $2 million of the diverted funds.

More importantly, Cutler avoided permanent spousal support. Instead, he is required to provide temporary financial assistance for one year to allow Cavallari to relocate and stabilize financially, while he retains custody of their three children.

Speaking outside the courthouse, Cutler said: “As a husband and a father, I gave my trust and my best years. But when someone tries to take everything you’ve worked for, you have no choice but to fight. I believe in fairness — she’s entitled to her share, but she can’t take it all.”

Legal experts say the ruling sets a strong precedent for high-profile athlete divorces, where hidden assets and excessive demands frequently emerge. Bears fans on social media hailed Cutler’s victory as “a Hail Mary for the ages” in a career defined by resilience.

For Bears Nation, the win resonates deeply. Jay Cutler built his name on toughness and perseverance, and even more than a decade after leaving the field, he has shown once again that champions shine brightest under pressure.

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Ravens Fan-Favourite CB Faces Family Tragedy After Week 5 Game as Military-Trained Skydiving Instructor Dies in Nashville
Baltimore, MD – October 8, 2025Baltimore Ravens second-year cornerback Nate Wiggins is mourning a profound personal loss following the team’s Week 5 matchup, as his cousin, Justin “Spidey” Fuller — a respected military-trained skydiving instructor — died in a tragic tandem jump accident outside Nashville. Fuller, 35, was fatally injured after becoming separated from his harness mid-air during a jump organized by Go Skydive Nashville. His student survived after landing in a tree with the parachute deployed and was later rescued by firefighters. Police confirmed Fuller’s body was recovered in a wooded area off Ashland City Highway. The Nashville Fire Department called it “one of the most complex high-angle rescues in recent years,” commending personnel for their efforts. Known by the nickname “Spidey,” Fuller died after a tandem skydive went wrong on October 4, 2025, near Nashville, Tennessee. (Facebook/Justin Fuller Spidey) Beloved in the skydiving community, Spidey had completed more than 5,000 jumps and helped train U.S. service members in advanced aerial maneuvers. Friends described him as “fearless, focused and devoted to lifting others higher — in life and in the air.” Wiggins — whose mother is the younger sister of Fuller’s mother, grew up admiring his cousin’s discipline and sense of purpose. Family members say that influence helped shape his mental toughness and leadership on the field. A relative told local media, “Justin taught Nate that strength isn’t about being unbreakable — it’s about standing firm when life hits hardest. That’s exactly how Nate lives and plays today.” Wiggins, a former first-round pick from Clemson, has steadily earned the Ravens’ trust as a rotational cornerback in nickel/dime packages, praised for his speed, press technique, and ability to carry deep routes. Coaches describe him as “wise beyond his years,” calm under pressure, and disciplined at the catch point. Through the first five games of 2025, he has 12 solo tackles, 4 passes defensed, and 1 interception, reinforcing his value on the perimeter.  The Ravens organization has provided time and private support for Wiggins and his family, ensuring he can grieve without team-related obligations. Teammates have stood beside him, honoring both his resilience and his family’s tradition of service. The FAA is investigating the incident, while tributes to “Spidey” continue to pour in on social media from military colleagues, fellow skydivers, and fans across the country.“He taught others to fly — now he flies higher than all of us,” one tribute read. Wiggins kept his public comments brief, speaking softly before being embraced by teammates:“Spidey always told me not to fear the height — only the moment you forget to look down and pull someone else up with you. This week, I’m playing for him.”