1996 - Robert inherits a great deal of money from a distant and very rich relative. It purchases a civic center in Sueño Beach, Florida. He hires old friends, Dean "The Ninja" Christian and "Crazy" Andy Perry to help him set-up shop.

1998 - Robert opens up the new incarnation of the Imaginary Wrestling Association in October. He gives Dean Christian a job as a referee upon his request, and "Crazy" Andy becomes the first announcer hired by the IWA. "Nightmare" Joey Summers, despite their rivalry, shows up the day before the first show and asks for a job. Robert hires him as yet another announcer. He also hires his first wrestlers: Mr. Taste, John "The Equalizer" Powers, Ezekiel, Omega, Red Dog, and Suicide. Ezekiel becomes the first World Heavyweight Champion. Night of Hell is the IWA’s first pay per view, where Knightmare defeats Ezekiel to become the new World Champion. Daniel James is named Commissioner while President Robert Chauncey goes on an extended Christmas Vacation.

1999 – Robert suspends Daniel James for abuse of power for six months. Superstars such as Shadow, Thunder, Fenris, Downfire, and Uzu all enter into the IWA. Damage wins the World Heavyweight Championship. Mr. Nobody makes his first appearance in the IWA, kidnapping Robert and claiming to be in charge. Damage is fired suddenly for problems backstage. The World Title is vacant. At Armageddon, Mr. Nobody sets up a World Title match between the top four stars in the IWA at the time, Thunder, Shadow, Mark Damian, and The Unforgiven. Thunder wins. Robert returns, reclaiming control of the IWA back from Nobody, only to have Nobody disappear. Nobody returns only to wage war once again on Robert and the IWA. Mr. Nobody is discovered to be former Commissioner Daniel James. Nobody plunges from a three tier cage to the floor below and is taken to the hospital disappearing from public eye. Chip Dobbs becomes IWA Vice President.

2000 – Superstars such as Jason O’Kelly, Ego, Magnum, and Animal rise to stardom in the IWA. Jason Hartnell captures the World Heavyweight Championship. Jason Hartnell is fired due to severe backstage problems with several wrestlers and staff members. Mysterious attacks plague members of the IWA staff. It is discovered to be David Skinner, a member of Jonathon Rook’s security detail. Skinner is fired. It is learned that Robert is having money problems keeping the IWA open, despite its success. Jonathon Rook marries former IWA Vice President, Kristina Chapman. Jonathon Summers III becomes partners with Robert in the IWA. Christopher Alexander Rook is born to the proud parents of Jonathon and Kristina Rook. Robert is severally injured at the hands of The Unforgiven. Summers becomes temporary President until Robert’s return. Summers fires Vice President Dobbs and Commissioner Weird Mystery. Summers forms the Insurrection as a revenge plot against the IWA for his childhood friend, Daniel James. He brings in Daniel James as the new Commissioner. Insurrection crushes through the competition capturing all the titles in the matter of a month’s time. Robert comes back and leads the fight against Insurrection. Summers is screwed by James and is forced out of the IWA forever. Robert tries to fire James, but is unable to due to his contract. After almost a year of absence, Knightmare returns to the IWA to capture the World Title in his first match back. James interferes in a match which violates his contract. Robert fires him. James returns with a vengeance. A match is set-up between James and Robert, winner takes the IWA. Robert is screwed by both Weird Mystery and Dalios, allowing James to win. James is now in control and has changed the IWA to the NWA.