Tony was chewing at the leash before IM1, which is why Obie was okay with cashing him in, even though it meant killing the golden goose.
But then Tony not only survives, he comes back harder to control, and not in the way he’d previously been difficult (ditching the award ceremony to play craps, needing regular check-ins and emotional work). Now Obie realizes he can’t read him, Tony’s traumatized restraint isn’t a petulant mood he can literally handle him out of–when Obie tries, it only makes Tony more distant. Instead of having to cajole him into making presentations, Obie now has to distract him from taking too much interest in the business and making decisions without his counsel. Suddenly Tony’s keeping projects and parts of his house secret from him, defending boundaries all over.
This pushback puts Obie on the back foot more than the failed assassination did, and he decompensates and escalates into physical abuse pretty quickly. In the context of Obie being there to pick up the pieces after Maria and Howard died, you really get how insidious that guy’s been since Tony was a (vulnerable grieving) teenager.
It doesn’t work anymore because Tony’s spent weeks of intense quality time with Ho Yinsen, MD.
Yinsen repairs Tony’s heart, and puts a shield around it. Yinsen asks Tony simple questions that have very profound answers. Yinsen demonstrates calm abiding heroism, and the confidence that Tony is also capable of it. Yinsen does all of this while deeply grieving his family. A gifted surgeon, a man of faith, a father and husband, and someone with more love, compassion, true optimism, and mentorship in his little finger than Obie’s ever faked.
And it’s increasingly, painfully, creepily obvious to Tony way before he learns of the real betrayal.
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