Who's going to pay for an AM station now? And pay enough to make a substantial dent in Entercom's debt?
If anyone was in the market for a Chicago AM, you'd think they could have or would have already bought WLS-AM (Cumulus has been clear about wanting to exit the largest markets especially where it has a small station portfolio) or WGN-AM, which is Nextstar's one and only radio station and which they seem to be ambivalent about owning.
Cumulus is generally shedding stations, not buying. So that leaves iHeart, Hubbard, or smaller groups and the brokered / ethnic / religious operators. None of those seem plausible to me and I don't see a John Catsimatidis waiting in the wing to snap up 780 ala WABC, either. Besides the fact that neither Cumulus or Nextstar have managed to unload 720 or 890, just look back to Merlin's sale of WLUP and WKQX -- either of which are arguably more valuable signals now than an AM station, even a 50kw one. EMF bought one, and WKQX went to Cumulus by default. Sold for $21M and $17M. I think your guess of $7M for WBBM-AM is close if not high.
As for US99: why would Entercom flip it? US99 still leads Big country and there have been plenty of rumors of iHeart pulling the plug on Big, so Entercom can just wait out iHeart and possibly get format exclusivity back. Plus, as others have noted, it currently costs near nothing to run.
And what would Entercom flip 99.5 to? They already had classic hits on 104.3 and gave up. I don't see them trying alternative, which could hurt XRT. I'd think the same would apply to classic rock, but maybe the Drive's fat ratings look tempting. I guess I could see a simulcast of the Score on FM, but I'm still skeptical Entercom would give up on US99 for sports at a time when we don't know if there will be sports next week and the Score and ESPN1000's ratings are already dropping.
Lastly, sorry to be a contrarian, but I don't think the failure of AM stereo did that much to kill the AM band. Maybe that was one of the factors back in the 90s that helped push things on their way, but before the more recent decline, AM has had a pretty good second life as a home for primarily spoken word (news, talk, sports) programming.
The larger factors in the current decline of AM seem to me to include the rise of streaming, the constantly rising noise floor thanks to RF polluters like cheapo Chinese LED bulbs that can make listening to AM tedious, declining support for AM radio in receivers (AM band absent entirely or tuner is so poor it might as well be), and the consolidation and decline of the radio industry in general (less content / poorer content leads to less listeners which leads to less revenue which leads to less content / poorer content…).
There are also the just fundamental technical disadvantages that AM has vs FM and streaming in terms of signal bandwidth / fidelity / susceptibility to lightning interference, etc. AM stereo doesn't fix any of those (except maybe fidelity, but … the other issues overwhelm that one).
Yes, it's great that you can kinda hear 670/720/780 across the Midwest, and I say that as someone who loves to catch DX, but to me, AM radio is like not far from the telegraph and dial-up modems. It’s a product of another age that has almost outlived its usefulness.
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