For the last 60 years, Generalized Expected Utility Theory, Rational Expectations, and tacit presumptions of symmetry in outcome distributions have been the foundational mainstay in decision-making paradigms which seek optimum risk tempered outcomes. Portfolio evaluation tools like Sharpe and Sortino ratios, which focus on risk modulated average returns, epitomize the practice. Recently, an alternative Probability Dominance heuristic has been posited with a focus on most likely outcomes as the basis for choice. When outcome distributions are symmetric unimodal, expected and most likely outcomes coincide, and choice can be construed as being made on the basis of either. However, when outcome distributions are not so structured, expected outcomes will not be the most likely. Here, the question as to whether choice should be most likely or expected outcome based is raised, the impact of taking a “Most Likely” view of the world examined and “Most Likely” focused versions of the Sharpe and Sortino Ratios introduced. Simple exercises performed on commonly used benchmark portfolio and stock returns data demonstrate that expected and most likely returns frequently diverge and trend in opposite directions so that portfolio orderings change substantially when alternative heuristics are employed.