So you're saying that the defunct Morag-Tong, the government-sanctioned group of assassins from Morrowind, which is in a great deal of turmoil btw, you're saying that these people have put an assassin in the ranks of a not-very-powerful Jarl of Skyrim for YEARS on the off-chance that they might need him dead?
SPOILER AHEAD
You're saying this AFTER an actual former-Morag-Tong assassin confirmed that the group is pretty much gone IN-GAME?
Yes, the dead group of assassins from a strife-ridden country have put a long-term assassin in the court of a powerless member of Skyrim society. That's what happened.
Congrats, you figured it out.