Chicago Bears star quarterback Caleb Williams appears to be winning both on and off the field.
and their star quarterback Caleb Williams just pulled off one of the most thrilling comeback playoff victories in recent memory against the Chicago was trailing to their divisional rivals 21-3 at halftime and 21-6 heading into the fourth quarter before mounting the formerJan 10, 2026; Chicago, IL, USA; Chicago Bears quarterback Caleb Williams and wide receiver DJ Moore react after hooking up on the eventually game winning touchdown against the Green Bay Packers during the second half of an NFC Wild Card Round game at Soldier Field.
Mandatory Credit: Matt Marton-Imagn Images | Matt Marton-Imagn ImagesGiven that Williams has quickly blossomed into one of the NFL's biggest stars, his personal life has become a common topic of conversation. The prevailing rumor right now is that Williams is dating 28-year-old model Ashaley Kaashh, as there have been several suggestions that these two could now be a couple, although neither has confirmed it directly.Ashaley kept it coy when a fan wrote, “Anyone having people over to watch the @ash.kaashh Bowl tonight??? 🧀🐻” on their Instagram story before Saturday's Bears vs. Packers game.Caleb Williams’ rumored girlfriend Ashaley sends bold message after Bears’ big win Ashaley was indeed at Soldier Field for Saturday's big game. And she wasted no time flexing what appeared to be a giant fur coat after the comeback victory. She posted several Instagram story videos of her seemingly walking out of Soldier Field. The song, BLOUSIN by Rob 49, was playing on the video, and the lyrics, "Biggest in this -, man," could be heard.Perhaps Kaash is Williams' good luck charm, because both he and the Bears have been playing great ever since the dating rumors between them started.Grant Young covers the Athlete Lifestyle, Women’s Basketball, the New York Mets, the Baltimore Orioles, the Chicago Cubs, and boxing for Sports Illustrated’s ‘On SI’ sites. He holds an MFA degree in creative writing from the University of San Francisco , where he also graduated with a Bachelor’s Degree in Marketing and played on USF’s Division I baseball team for five years.
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