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He won’t tolerate anyone questioning his decisions.

In the above sentence, is 'questioning' a gerund (as part of the object of the verb 'tolerate')?
Or is it a participle, modifying the pronoun 'anyone'?

I would say a gerund. The basic sense is 'he won't tolerate questioning' rather than 'he won't tolerate anyone'.

Some traditionalists might say that a gerund should always be preceded by a possessive, e.g. 'he won't tolerate your questioning his decisions' or 'he won't tolerate John's questioning...', but when the noun/pronoun is not personal, as in this case, it's definitely OK not to use the possessive because the result sounds unnatural, i.e. 'He won't tolerate anyone's questioning his decisions.'