How did the Jesuits go from the most conservative to the most left-wing religious order so quickly? Or am I wrong?
You are wrong. They’ve been that way for decades. Their influence in the American labor movement is longstanding. e.g. the Xavier Labor School in NYC (one of many)
The Jesuits were extreme leftists when I was a freshman at a Jesuit High school in 1967. I remember one Jesuit priest who might have been a conservative, but he has been dead for a long time.
I attended a Jesuit university decades ago and the Jesuits were worldly and rather left-leaning even back in those days. Their left-wing views are not a recent development, sorry to say.