Most observed multi-planet systems are coplanar, in a dynamically “cold” configuration of concentric orbits like our own Solar System. I will present the first images of 14 Herculis c with the James Webb Space Telescope (JWST) NIRCam coronagraph. This mature, cold gas giant is the first exoplanet directly imaged in a dynamically “hot” system. With large eccentricities and a nonzero mutual inclination, the architecture of this system points to a turbulent past and dramatic ongoing angular momentum exchange between the planetary orbits. The temperature of the planet (~275K) rivals both the coldest imaged exoplanets and the coldest known brown dwarfs, while its photometry at 4.4 microns is consistent with the presence of carbon disequilibrium chemistry and water ice clouds in the atmosphere. 14 Her c presents a unique laboratory to study many aspects of giant planet formation and evolution simultaneously, and is an exciting demonstration of the mid-infrared high contrast performance of JWST. I will also present on preliminary work to image HD 222237 b, a cold (~200K), nearby, eccentric giant planet with JWST.