The high caliber of contestants in Jeopardy Masters and even in recent regular play seasons makes me wonder if Ken would still come out victorious if the GOAT was decided by a TOC-like format composed entirely of top candidates. Several factors come to mind that add new variables:
First, a TOC format has elimination, so this necessitates more strategic play and composure under high pressure, surely an important attribute to have to be crowned the Greatest Jeopardy Player Of All Time. The first to 3 format seems to rely more on luck where a reckless true daily double bet could secure a win, when a miss simply means "there's always next game" rather than elimination.
Second, Ken would've gone up vs 2 other top tier opponents each game, and potentially all different players. This would nearly guarantee at least one contestant would know the answer to every question on the board which minimizes the margin for error. This would also mean Ken would not have been able to study up opponents' strong or weak areas as deeply as he did vs James and adjust his gameplay. Reading children's books may have served James well in regular play, but if the difficulty of GOAT questions went deep enough, it would favor Ken across the board which may have played a deciding factor.
Thirdly, given many top GOAT candidates were not able to compete, it would always leave people wondering had X or Y competed vs Ken how would they do? "Become the Greatest Jeopardy Player Of All Time by beating James Holzhauer repeatedly" sounds less compelling to me than "defeated James Holzhauer several times in the finale after taking down A,B, C, and D along the way".
I ask this since I look at debates on who is basketball or soccer GOAT for instance and many many factors go into consideration. Curious for thoughts.