We report the discovery of two short-period massive giant planets from NASAs Transiting Exoplanet Survey Satellite (TESS). Both systems, TOI-558 (TIC 207110080) and TOI-559 (TIC 209459275), were identified from the 30-minute cadence Full Frame Images and confirmed using ground-based photometric and spectroscopic follow-up observations from TESSs Follow-up Observing Program Working Group. We find that TOI-558 b, which transits an F-dwarf ($M_{star}=1.349^{+0.064}_{-0.065} M_{odot}$, $R_{star}=1.496^{+0.042}_{-0.040} R_{odot}$, $T_{eff}=6466^{+95}_{-93}$ K, age $1.79^{+0.91}_{-0.73}$ Gyr) with an orbital period of 14.574 days, has a mass of $3.61pm0.15 M_J$, a radius of $1.086^{+0.041}_{-0.038} R_J$, and an eccentric (e=$0.300^{+0.022}_{-0.020}$) orbit. TOI-559 b transits a G-dwarf ($M_{star}=1.026pm0.057 M_{odot}$, $R_{star}=1.233^{+0.028}_{-0.026} R_{odot}$, $T_{eff}=5925^{+85}_{-76}$ K, age $1.79^{+0.91}_{-0.73}$ Gyr) in an eccentric (e=$0.151pm0.011$) 6.984-day orbit with a mass of $6.01^{+0.24}_{-0.23} M_J$ and a radius of $1.091^{+0.028}_{-0.025} R_J$. Our spectroscopic follow-up also reveals a long-term radial velocity trend for TOI-559, indicating a long-period companion. The statistically significant orbital eccentricity measured for each system suggests that these planets migrated to their current location through dynamical interactions. Interestingly, both planets are also massive ($>3 M_J$), adding to the population of massive hot Jupiters identified by TESS. Prompted by these new detections of high-mass planets, we analyzed the known mass distribution of hot Jupiters but find no significant evidence for multiple populations. TESS should provide a near magnitude-limited sample of transiting hot Jupiters, allowing for future detailed population studies.
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