Microsoft: Risk Exceeded Reward
Microsoft is under review by the EU with regard to two of its keystone products, Windows 7 and IE. This was a far less than ideal time for Microsoft to appear to be stomping on a European company with significant financial problems. This is a lesson it should have learned from Netscape which, after it died, has done (and continues to do) more damage to Microsoft than any surviving competitor has ever done.
There is an old saying about never kicking a dying man. TomTom appeared to be failing and was likely to lash out, as it did, creating untimely problems for Microsoft. It is still likely that whatever revenue Microsoft gets from this deal will be overwhelmed by difficulties with the EU resulting from the coverage.
This equates to a lot of damage to FLOSS' credibility, Tom Tom's likelihood of survival is reduced, and Microsoft's anti-trust defense is weakened for a small amount of fleeting press coverage. At least with Microsoft, the press coverage wasn't intended, but its likelihood was also never in doubt. In all cases, this reflects what appears to be a lack of strategic thinking and if there was ever a year to think strategically, 2009 is that year.