Semantic degeneracy represents a fundamental property of natural language that extends beyond simple polysemy to encompass the combinatorial explosion of potential interpretations that emerges as semantic expressions increase in complexity. In this work, we argue this property imposes fundamental limitations on Large Language Models (LLMs) and other modern NLP systems, precisely because they operate within natural language itself. Using Kolmogorov complexity, we demonstrate that as an expression's complexity grows, the amount of contextual information required to reliably resolve its ambiguity explodes combinatorially. The computational intractability of recovering a single intended meaning for complex or ambiguous text therefore suggests that the classical view that linguistic forms possess intrinsic meaning in and of themselves is conceptually inadequate. We argue instead that meaning is dynamically actualized through an observer-dependent interpretive act, a process whose non-deterministic nature is most appropriately described by a non-classical, quantum-like logic. To test this hypothesis, we conducted a semantic Bell inequality test using diverse LLM agents. Our experiments yielded average CHSH expectation values from 1.2 to 2.8, with several runs producing values (e.g., 2.3-2.4) in significant violation of the classical boundary ($|S|\leq2$), demonstrating that linguistic interpretation under ambiguity can exhibit non-classical contextuality, consistent with results from human cognition experiments. These results inherently imply that classical frequentist-based analytical approaches for natural language are necessarily lossy. Instead, we propose that Bayesian-style repeated sampling approaches can provide more practically useful and appropriate characterizations of linguistic meaning in context.