In its latest attempt to take down Google with a negative fervor unseen since, well, November, Microsoft has begun a three-month advertising campaign for Hotmail's replacement that will cost between $30 and $90 million — and focus almost entirely on how terrible Gmail is. Microsoft believes its latest round of Google attack ads, which started to roll out a couple of weeks ago, represent "the biggest marketing blitz in the history of email," reports The Associated Press. The attack ads are running just as Microsoft makes its Outlook.com email service mandatory for mail users (it launched in preview last summer). Starting today all existing Hotmail users will find their emails migrated over to the quite attractive looking Outlook.com, but Microsoft will try to win over new users with an onslaught of advertising that focuses on how bad the competition is — a negative strategy Microsoft has now pushed for some time. 

The new anti-Google ads feel more like advocacy than advertising. In the first spot, a concerned voice educates Gmailers about how Google sifts through all our information — for about 78 seconds. Only in the last three seconds does Microsoft's new Outlook even get advertised:

This 30-second spot doesn't mention Outlook.com until the very last second, either, after explaining how Google can misinterpret information to deliver misleading ads:

Microsoft has countered Google's heartstrings approach with negative campaign strategy in part thanks to the guidance of Mark Penn, a political and media strategist who worked under Bill Clinton and with Hillary Clinton during her presidential campaign run in 2008. Microsoft hired him in July 2012, and the company has made its advertising more like negative political spots ever since.

Of course, it's not clear if any of the negative advertising actually works. The bloggers say no. Only about 9,775 people have signed Microsoft's Scroogled petition, which is a tiny percentage of Gmail's 300-million user base, argues Search Engine Land's Danny Sullivan. But the full onslaught has yet to come, with millions more and three months — and ad spending of at least $30 million gets you some pretty prime(time) eyeballs. Plus, in politics, the negativity works