Speculating further:
His relationship with the CIA began in the early 80’s after the Russian invasion of Afghanistan. We did covertly support the mujaheddin back in the day.
He was an asset of value based on his close relationships to several lawmakers on both sides of the aisle into the 90’s.
I will speculate further and say he was again an asset when we were planning the Afghanistan invasion after 9/11.
When the WH was floating the idea of a treaty with the taliban, he may have been approached for input, which would explain his visits to the State Department and (if reports are confirmed) the WH.
Common sense tells me the above is the only reason his pro-taliban, anti-US rants on his broadcasts were tolerated without any alarm. “Seddique? He's harmless. He's one of us.” or “Omar is Seddique’s son. He is as harmless as his Dad.”
If my speculation is close to reality, I am guessing the feds had an “oh shit!” moment after the attack after realizing Seddique was not as harmless (or stupid) as they thought, and had been plying them all along.
That would certainly explain how they so quickly ‘’lost’ Omar’s wife.
A very BIG “oh s#it moment.”
I’ll be Mateen’s wife is never seen again. Gone in the wind, or fed to the gators.