I think it is also worth noting that English will indeed evolve, inasmuch as linguistic evolution is exasperated by social change. This is evident in English, as if 1066 hadn't happened, and Norman French hadn't influenced the Germanic Old English, our current vocabulary might not be so Latinate. We can contrast the quick evolution of English with the linguistic conservatism of languages such as Modern Icelandic, which is almost mutually intelligible with Old Icelandic, or West Norse, a language contemporary with West Saxon.
Current English will evolve into manifold dialects, each reflecting the unique social environments and social history that will follow. This is all unavoidable and unpredictable.
More interesting in my mind, is how languages such as Classical Latin became codified, whilst social change still caused a divergence of dialectal change in certain regions (e.g. Gallic Vulgar Latin vrs Spanish Vulgar Latin), and whether a codification might happen to English in any form at any time.
By the way, it is interesting that you mention Ladino, as there is also a new English dialect that is spoken here in my home state of New York, called Yeshivish. It is a pseudo-dialect of English spoken in Jewish learning environments among the orthodoxy here in NY, and is highly influenced by Babylonian Aramaic, Hebrew, and Yiddish. It's a good example of regional dialectal change already occurring on a small scale.