Never. ENTERCOM can't afford to forfeit another FM signal in Market #3.
The only reason 105.9 is still being utilized this way is due to sports (football) spillover.
Bottom line, even more detailed, the revenue formula today supports WCFS/WBBM-AM. To take WJMK as a simulcast is suicide when you are doing a market cluster revenue competition with iHeart, Hubbard, Cumulus etc....
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