Chris met Gary Gygax when he was 15 at one of their 'mini-Gen Cons' at the Horticultural center. Gary was running a miniatures game of Chainmail (the fantasy supplement) that Chris played in. They immediately hit it off, so much so that Chris started running events at Gen Con the very next year. Eventually, Gary had Harold Johnson offer Chris a job at TSR in 1979, (which he refused, it was full time and I wanted to finish high school), but they stayed in touch over the years. After Chris started the Inner City Company, Gary always made sure that Chris got an invite to the "TSR Party" at Gen Con, and Chris got to know several of the crew that way. When the 'TSR crash' hit in 1995-1996, and there was zero production of material for the 2nd Edition, Chris decided to start writing generic adventures that might fill that void, and he thought he would call Gary and see if Gary was interested in developing these adventures with Chris (for a paycheck). Chris didn't know if Gary was desperate, or just liked him that much, but Gary agreed. Gary and Chris wrote "A Challenge of Arm's" and "The Ritual of the Golden Eyes" as 'works for hire' as the developer and writer, and they got to know one another and became fast friends. When Gary could find no investors to underwrite the Lejendary Adventure, he called Chris, asked if he would form a company with him, and Hekaforge Productions, a Limited Partnership, was born.
Then they REALLY started spending a lot of time together.
By the time 2006 rolled around, Chris's ability to continue pushing the Lejendary line forward had about played its part, so he suggested to Gary that they find an 'angel' and Chris approached the Troll Lords with the Lejendary License on Gary's behalf (at the GAMA trade show that year). Gary then cut his own deal with the Troll Lords, but Chris and Gary remained good friends up until Gary's death. Gary and Chris still wrote a few things together, but mostly along the lines of, "hey could you take a look and give me your $0.02" rather than anything official. Most of the time they just traded e-mails every other day or so.
From the age of 15 until the day he passed from this Earth, Gary taught Chris a lot: about writing, design, humor, and frankly, life, and Chris carries those lessons with him to this day.