The Dickeys own a fraction of Cumulus. They serve at the behest of the major shareholders. Crestview Partners has 15 times more shares than Lew Dickey. Crestview has 12 times the number of shares than Lew and John Dickey combined. They could be out in a heartbeat if Crestview decides they're not doing the job. Crestview ended up with the company because the Farid-led version of Citadel went bankrupt. The Citadel/Cumulus merger was determined by Crestview's decision, not the Dickeys.
iHeart is privately held because there's no way that they can sell off their assets, or generate enough money from an IPO to offset their massive debt. They may as well operate and put off the bankruptcy for as long as possible so they can reap some profit while they can. Their exhorbitant refinancing terms and the sell-off of tower properties give you a clue as to where they expect to be in the future. Bain Capital, LLC and Thomas H. Lee Partners will do their best to get their money out of iHeart before the eventual collapse. If it survives, they'll have already made their money, and will be happy to part with it. Bain and Lee essentially got stuck with the company in 2008 because Clear Channel had borrowed so much money from them. There's a reason that the Mays family is no long part of the management.
iHeart is privately held because there's no way that they can sell off their assets, or generate enough money from an IPO to offset their massive debt. They may as well operate and put off the bankruptcy for as long as possible so they can reap some profit while they can. Their exhorbitant refinancing terms and the sell-off of tower properties give you a clue as to where they expect to be in the future. Bain Capital, LLC and Thomas H. Lee Partners will do their best to get their money out of iHeart before the eventual collapse. If it survives, they'll have already made their money, and will be happy to part with it. Bain and Lee essentially got stuck with the company in 2008 because Clear Channel had borrowed so much money from them. There's a reason that the Mays family is no long part of the management.