News sites have to spend X% of their margin to continuously generate content to attract viewers, while big tech companies spend 0 to attract viewers because viewers are the generators of their content. For this fundamental reason, news sites never be able to compete on targeting granularity or ad pricing.

Rather than fighting a losing battle, it's better to put your chips behind a battle where you have a differentiated advantage (in the NYT/Cable News companies, it's the cornered resource of accredited voices in reporting and editorial).

It would be net-negative to try to compete in the space targeted ads. They'd be better off offering low-revenue, low-cost blanket ads (i.e. advertise in the "automotive" section of the website to non-subscribers), where the cost to the ad operator is effectively zero because they don't have to maintain a database of user ad profiles.