Regarding Google, didn't Murdoch complain about just that? [2]
[1] Well, at least The Times and The Guardian. http://www.guardian.co.uk/media/2010/jul/20/times-paywall-re... mentions a daily loss of £240,000 for The Times, and http://www.guardian.co.uk/media/2010/jun/10/guardian-media-g... suggests similar (if not as great) losses by The Guardian. http://moreintelligentlife.com/content/ideas/tim-de-lisle/ca... suggests a calculation of £100,000 a day. However, The Telegraph appears to make a profit, as suggested here because of merging their digital and print media: http://www.guardian.co.uk/media/2011/mar/18/telegraph-group-... — though I get the feeling that it would still be funded somewhat past the point of profitability too…
[2] http://www.guardian.co.uk/media/2010/apr/07/rupert-murdoch-g...
However, I think even Mr Murdoch's personal wealth could not sustain the losses of digital news outlets should Google comply and stop indexing them. By any means, they just have to put a little piece of text in their robots file to do just that - so this is yet more talk in favor of strong copyrights, and no action to renew anything.
We see first hand what happens when disrupting incumbents who happen to also control politicians and have some good friends in the legal system. Hopefully the current people movement against copyright mafia will see further victories...