This just looks like an instance of using contradictory language to indicate that Tom fits the the conventional definitions of neither a bachelor or a married man. You could also say Tom is a single spouse. Bachelor happens to have connotations of referring to lifestyle rather than legal status which makes your meaning plainer. The fact that language is flexible enough to get around logic doesn't mean married bachelor isn't a logical contradiction or that Kant is wrong.
My point is that we have words because they call out a useful, albeit fuzzy, blob of conceptspace. We may try to claim that two words mean the same thing, but if there are different words, there's probably a reason -- because we want to reference different concepts ("connotations") in someone's mind.
It's important to distinguish between the concepts we are trying to reference, vs. some objective equivalence we think exists in the territory. The territory actually includes minds that think different thoughts on hearing "unmarried" vs. ...
This is our monthly thread for collecting these little gems and pearls of wisdom, rationality-related quotes you've seen recently, or had stored in your quotesfile for ages, and which might be handy to link to in one of our discussions.