When you buy a domain name that has been penalized by the search engines in the past, you put your enterprise's search marketing campaign on the line.
So how can you know if the domain you are keen on acquiring is out of favor with Google and Bing? Google's head of search spam Matt Cutt's has provided some decent answers in his latest Webmaster Help video.
"How can we check to see if a domain (bought from a registrar) was previously in trouble with Google? I recently bought one, and unbeknownst to me the domain isn’t being indexed and I’ve had to do a reconsideration request. How could I have prevented that?"
Cutts offered a few suggestions in the video (seen below) about preventing the situation from happening in the first place. The first suggestion was to search for the domain (using the site:domain.com command); no results all all should raise teh red flag. Cutt's other suggestion was to search for the domain at Archive.org, which shows what previous versions of the site looked like (and could shed light on the reason a penalty might exist).
If you have acquired a domain in the past which is still suffering from a Google penalty, do consider making a reconsideration request, disavowing links to the domain before submitting.