Thousand Dollar Can't Beat Karen: Listen for Your Chance to Win a $100 Stop & Shop Gift Card

For the Listen for your chance to play Thousand Dollar Can’t Beat Karen contest, enter by listening from 9:00 am (ET) to 10:00 am (ET) on Monday, December 8, 2025, through Friday, December 12, 2025, for the cue to call. Upon hearing the cue to call, be one of the first five (5) callers at 1-800-949-1027. Each of the first five (5) callers will each have the opportunity to answer one (1) pop trivia question off-air for the chance to play the on-air game against Karen Carson. The one (1) caller that the station staff determines to have the best audio quality, phone connection, and clarity from among the first five (5) callers that morning will then advance to play the on-air “Can’t Beat Karen” game (each a “Finalist”). Shortly following being selected as a Finalist, the Finalist will then compete against Karen via telephone and be asked to correctly answer five (5) pop culture trivia questions. If the Finalist “Beats” Karen by answering more questions correctly than Karen does, then upon verification of eligibility, that Finalist will receive one (1) One hundred dollar Stop & Shop Gift Card (redeemable at any accepted locations, cannot be redeemed for cash or replaced if lost, stolen, or damaged, full terms and conditions can be found HERE) and an official “Can’t Beat Karen” mug (the “Qualifying Prize”) and will also receive one thousand dollars ($1,000) (the “Grand Prize”). The Grand Prize will be awarded in the form of a corporate check issued in the name of the Grand Prize Winner. Checks will be mailed approximately fourteen (14) weeks after the station receives all required paperwork back from each Grand Prize Winner. If the Finalist does not “Beat” Karen, the Finalist will only win the Qualifying Prize. The number of listeners winning $1,000.00 depends on the number of listeners beating Karen in the Can’t Beat Karen game. There will be up to five (5) Qualifying Prize winners. The gift card is valued at $100.00 and is courtesy of Stop & Shop. The Gift Card will be sent within 2 weeks via FedEx once all proper paperwork is completed. The “Can’t Beat Karen” mug is valued at $5.00 and is courtesy of WNEW-FM. The mug will be mailed out via USPS within four to six weeks. There will be up to five (5) potential Grand Prize winners. The Grand Prize is courtesy of WNEW-FM.  Otherwise, WNEW-FM’s general contest rules apply and are available by clicking here.