negative habit

Our son Theo has a habit of immediately contradicting his mom when she makes an observation or point. As the most recent example, at a funeral procession with many cars, my wife Sarah shared "they must be really loved with so many people in the procession". Theo immediately countered, the opposite and stated they may not be loved at all but could not defend the point on why there were so many cars. In isolation, the example can be explained in many ways. However, it is a habit our son exhibits across the range of topics from corrections (perceived as disobedience to us) to facts (perceived as ignorance to us) to general life observations (perceived as pursuing contradiction for the sake of contradiction). My only technique is to break down each instance in painful detail for all involved but it doesn't shake the habit. What thoughts do you have?