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The spat between Google, the owner of YouTube, and Viacom threatened to disclose millions of users' details in a copyright lawsuit. Viacom eventually compromised in the end and allowed the anonymised data to be handed over by Viacom, but privacy was very much still at risk.
This could have been the largest legal disclosure of data to date, and would have compromised many YouTube users' accounts, and dented the privacy record of what once was an independent video upload site, before Google bought it out in 2006.
Groupon, a 'deal for the day' website, was close to being acquired by Google, but failed at the last minute. Google was meant to have offered over $2.3 billion more than Yahoo!'s reported $3 billion offer, but was rejected.
This led to the media questioning why, and whether Google even had a chance in the first place. After talks brown down, it became apparent that though Google could have bought out right Groupon, it had failed for no apparent reason. The LA Times called it a "head-scratcher".
But Google took a confidence hit, and one hell of a public relations hit too.