- (August 8, 2012) Father of first child with his fiancée (now ex-wife), Kristin Cavallari, a son named Camden Jack.
- Traded to the Chicago Bears for Kyle Orton and three of the Bears's picks, including the 18th overall pick in the 2009 draft. (April 2009)
- Drafted by the Denver Broncos with the 11th overall pick in the 2006 NFL Draft.
- (April 26, 2011) Engaged to Kristin Cavallari.
- (July 25, 2011) Briefly ended engagement to Kristin Cavallari.
- (November 30, 2011) Engaged again to Kristin Cavallari.
- His ex-wife Kristin Cavallari gave birth to their 2nd child, a son named Jaxon Wyatt Cutler, on May 7, 2014.
- His ex-wife Kristin Cavallari gave birth to their 3rd child, a daughter named Saylor James Cutler, on November 23, 2015.
- Ex-son-in-law of Dennis Cavallari and Nicole Cavallari.
- Ex-brother-in-law of Michael Cavallari.
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