Abstract We report the discovery of two short-period massive giant planets from NASA’s 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 TESS’s follow-up observing program working group. We find that TOI-558 b, which transits an F-dwarf (M _* = 1.349 − 0.065 + 0.064 M _⊙, R _* = 1.496 − 0.040 + 0.042 R _⊙, T _eff = 6466 − 93 + 95 K, age 1.79 − 0.73 + 0.91 Gyr) with an orbital period of 14.574 days, has a mass of 3.61 ± 0.15 M _J, a radius of 1.086 − 0.038 + 0.041 R _J, and an eccentric (e = 0.300 − 0.020 + 0.022 ) orbit. TOI-559 b transits a G dwarf (M _* = 1.026 ± 0.057 M _⊙, R _* = 1.233 − 0.026 + 0.028 R _⊙, T _eff = 5925 − 76 + 85 K, age 6.8 − 2.0 + 2.5 Gyr) in an eccentric (e = 0.151 ± 0.011) 6.984 days orbit with a mass of 6.01 − 0.23 + 0.24 M _J and a radius of 1.091 − 0.025 + 0.028 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 giant planets identified by TESS. Prompted by these new detections of high-mass planets, we analyzed the known mass distribution of hot and warm 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.