This doctoral thesis in mathematics consists of three articles that explore the probabilistic structure of quantum mechanics and quantization from a novel perspective.

The thesis adopts a probabilistic interpretation of quantum mechanics, which views the archetypical quantum experiments of Bell- and double-slit- type as violating the principle of non-contextuality, i.e., the assertion that all events and observables are always representable on one single Kolmogorovian probability space, rather than the principles of realism or locality. This probabilistic interpretation posits that quantum mechanics constitutes a probability theory that adheres to the principle of contextuality, and that quantum events explicitly occur at the level of measurement, rather than the level of that which is measured, as these are traditionally interpreted.

The thesis establishes a natural connection between the probabilistic structure of quantum mechanics, specifically Born’s rule, and the frequentist interpretation of probability. The major conceptual step in establishing this connection is to re-identify quantum observables instead as unitary representations of groups, whose irreducible sub-representations correspond to the observable’s different possible outcomes, rather than primarily as self- adjoint operators.

Furthermore, the thesis reformulates classical statistical mechanics in the formalism of quantum mechanics, known as the Koopman-von Neumann formulation, to demonstrate that classical statistical mechanics also adheres to the principle of contextuality. This finding is significant because it raises questions about the existence of a hidden-variable model of classical statistical mechanics of the kind as examined in Bell’s theorem, where this presumed hidden-variable model traditionally has been seen as that which distinguishes "classical" from "quantum" probability.A novel reformulation of quantization is proposed considering it rather in terms of the representation theory of Hamiltonian flows and their associated inherent symmetry group of symplectomorphisms. Contrary to the traditional view of quantization, this formulation can be regarded as compatible with the probabilistic interpretation of quantum mechanics and offers a new perspective on the quantization of gravity.