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Cutler's 'Soft Break-In' to Ex-Teammate's House
23 Nov, 2025
Summary
- Jay Cutler once entered a teammate's home unannounced at 6 AM.
- This occurred after a night out, with Cutler checking on his teammate.
- Cutler recently served jail time for a DUI conviction in Tennessee.
Kyle Long, a former Chicago Bears teammate, recounted an unusual incident involving ex-quarterback Jay Cutler. Long revealed that after a night of drinking, Cutler entered his house around 6 AM the next morning. Cutler's motive was to ensure Long was prepared for their scheduled workout, demonstrating a unique way of showing care.
This revelation comes to light following Cutler's recent legal troubles in Tennessee. The former NFL star was arrested for DUI in October 2024 in Franklin, a Nashville suburb. As part of a plea deal, Cutler was sentenced to a four-day jail term, though he served two and a half days.
Cutler, who was married to reality star Kristin Cavallari, has faced public scrutiny for his actions, including the DUI arrest and a subsequent civil lawsuit. His past relationship with Cavallari also remains a topic of public interest following their divorce.
