The lolsuit was a lawsuit filed in 2017 on behalf of Maddox. In this lawsuit, Maddox sued Asterios Kokkinos, Dick Masterson, a variety of other associates, Patreon, and a clerk who works at Patreon, for $20 million.
There was a great deal of complexity to the lawsuit, but the involvement of Asterios can be summed up by the fact that he made fun of Maddox on a Christmas album he recorded.
All claims were dismissed as frivolous and/or extremely disorganized by the judge.
Asterios first appeared as a guest in February 2019. He notably got along with Joe, considering him at first to be the "cool" one, much to the latter's delight. Halfway through the episode, however, he conceded that it was fun to make fun of Joe.
He returned to the podcast in November 2019, alongside Sirancha. On this episode, he continually shat on Joe for his terrible questions, but became a patron after being impressed with the quality of the ad reads.
Both Asterios and Sirancha have been invited back for a third (or in Sirancha's case, second) guest appearance. Asterios is tentatively slated to make a July 2020 return, with Lars finding renewed interest in having him on again after listening through The Biggest Problem in the Universe: Uncucked.