With the discovery of over 4000 exoplanets, we are now able to conduct detailed studies of planet demographics. Interestingly, a possible dichotomy has developed, where hot Jupiters on longer orbital periods (between 5 and 15 days) tend to be more massive on average compared to shorter period systems. It is not clear whether this trend is produced by a detection bias or whether it results from some aspect of the planet’s formation and evolutionary history. NASA’s Transiting Exoplanet Survey Satellite (TESS) provides an opportunity to probe this question by increasing the known population of long-period hot Jupiters. In this work, we focus on the confirmation and characterization of two TESS Objects of Interest, TOI-558b and 559b, giant planet candidates within this period range. We globally modeled the photometric data from TESS along with precise radial velocity measurements, and find that both planets are quite massive (3-6 MJ) and have highly eccentric (0.1-0.3), long period orbits (7 and 14.6 days). Finally, we include the systems in an analysis of the period-mass distribution of all known hot Jupiters, where we find tentative evidence for the existence of multiple populations. We will discuss these two new systems and their context within this population.