I think it was proven to be a format that fit well on one station. Personally, I can only hope to see a day when the same happens to Country. The "Jack-esque" station was a hole left when Mike was flipped to make room for WEEI on FM. Not counting to short lived format on 101.7 when iHeart assumed ownership from Phoenix Media.
My belief is that had CBS and Entercom not merge, 103.3 would still be Amp, and there wouldn't have been Big, Mike, Jack, or whatever. The only frequency left was 97.7. I would assume that keeping the "New" format that was assigned to it and WAAF still going away. The only other possibility would have been that either 97.7 went to EMF or WAAF became 97.7 exclusive. Either of those would have been my preference, but I see it as a pipe dream. More likely 97.7 stayed with a classic R&B format. That's just my belief. Either way, I don't see a competitor to WROR in a hypothetical different reality or this one.