The motivational value of the context is clearly demonstrated by students in classroom situations posing the title question. This excellent real-life question triggered the design of a special instructional sequence culminating in the addressed problem and aiming to combine different approaches to probability. Considering students’ usual struggle with the field, this attempt may prove valuable. As in the history of Stochastics, investigating the rationality behind the system of odds requires parallel handling of chances and expected value, and can lead to a deeper understanding of complex mathematical models. Recently, Series of Problems have been in the center of attention of the Complex Mathematics Education Research Project in general, as an important characteristic of the Hungarian Guided Discovery approach. Our design roots in this highly problem based tradition and adopts some of Tamás Varga’s ideas in instruction. In our paper, the details and structure of the designed teaching material will be displayed utilizing the tools of this research. Following centuries of tradition, sports betting is flourishing nowadays, particularly benefitting from the opportunities of online forums. Providing entertainment for many, it has great motivational value for students, who often pose the particular question in the title. This question is spot-on: gambling is a highly regulated, nevertheless always lucrative market. From an educational point of view, sports betting gives us a more complex perspective on probability than combinatorial games. History and teaching practice both suggest that the concept of probability bears serious cognitive load, and students often burdened with biases that makes the heart of the concept elude them. Furthermore, instruction sometimes lacks the adequate means to harmonize even the correctly introduced aspects of probability, leaving the students with either fragmented or contradicting ideas. In our paper we will make an attempt to connect the classical (laplacian), statistical (frequentistical) and subjectivistic (bayesian) approaches of probability through a gradually constructed task sequence organized around sports betting. We hypothesize that the investigation of the rationality of odds can foster a more integrated understanding of the concepts probability and expected value. Classification: D40, M10, K50, U30, U40, U60. Keywords: probability, expected value, risk, problem-solving, problem series, modeling, teaching process