Actually it makes no strategic sense at all. Due to the local-centric construction, installation and service requirements, the only thing they could save big $$ on would be their corporate overhead and at the end of the day that would be peanuts comparied to the free cash flow required to service a reasonable dividend.
Much better for both companies (and also more likely) is to cut the dividend (as Pitney and CTL did) and use some of the money to buy back shares and the rest to deleverage. This might be painful to shareholders in the short run but would be about the only way both of these dinosaurs could keep from becoming extinct.
Actually, the more effective tie-up would be FTR with CTL, as both of these stocks have already taken the necessary step of reducing theie dividends to stablize cash flow. Win, on the other hand,still has to swallow that necessary pill. Neither CTL nor FTR wants to go thorugh that process again. So the only way FTR will link with WIN, will be AFTER WIN cuts its dividend, too.