Here's an interesting political history of WebObjects around the time we last heard from it. As strange as it may seem, there's still an active WebObjects development community despite it being essentially self-supported for nearly a decade, now. Many of the developers in that community were, previously, Objective C developers, and the ones that survived the transition to Java are language agnostics. I suspect they might welcome the opportunity to migrate to a Swift/Cocoa web stack.
It will take some while, but Apple has just made the first step to a "language mindshare" play in the web application space.
Computers are unreliable, but humans are even more unreliable. Any system which depends on human reliability is unreliable. -- Gilb