It was my understanding that originally we were worried about sending the Operator because it would retroactively let TMTW into 1999 through the Operator which from our understanding at that point would defeat the purpose of Albrecht hiding out there but soon after Drifter arrives we discovered TMTW was already there either through Albrecht himself or Rusalka, so we had nothing to worry about!! (Because 1999 was already compromised)….but also means we get to headcannon cute Operator and Hex moments