Giant stars as known exoplanet hosts are relatively rare due to the potential challenges in acquiring precision radial velocities and the small predicted transit depths. However, these giant host stars are also some of the brightest in the sky and so enable high signal-to-noise follow-up measurements. Here we report on new observations of the bright (V ~ 3.3) giant star $iota$ Draconis ($iota$ Dra), known to host a planet in a highly eccentric ~511 day period orbit. TESS observations of the star over 137 days reveal asteroseismic signatures, allowing us to constrain the stellar radius, mass, and age to ~2%, ~6%, and ~28%, respectively. We present the results of continued radial velocity monitoring of the star using the Automated Planet Finder over several orbits of the planet. We provide more precise planet parameters of the known planet and, through the combination of our radial velocity measurements with Hipparcos and Gaia astrometry, we discover an additional long-period companion with an orbital period of ~$68^{+60}_{-36}$ years. Mass predictions from our analysis place this sub-stellar companion on the border of the planet and brown dwarf regimes. The bright nature of the star combined with the revised orbital architecture of the system provides an opportunity to study planetary orbital dynamics that evolve as the star moves into the giant phase of its evolution.
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