The federal government has never arrested anyone for taking ads.
The Sportingnews was a unique case - no one knows the details of the case because it was settled before it even became a case. It was kind of like the DOJ called up Paul Allen and said we need $7M to make this go away. It would not surprise me if someone inside the sportingnews was acting as an agent or taking bets (I have no idea) but it makes no sense that the DOJ took on one publishing company out of thousands. It is also unlikely that Paul ponied up $7M without as much as an appeal if he did not see wrongdoing as well...
Companies like Google and Yahoo advertised sportsbooks far more blatantly than thesportingnews yet never received a fine or indictment. The letter they received even went so far as to say you MAY be aiding and abetting meaning the DOJ does not even know if a court would uphold it.
The fact that companies that were taking far more ad revenues from sportsbooks did not get fined and the fact that Paul settled almost overnight makes me think more was going on.
In the BOS case, it is abundantly clear that the advertisers in FL were taking bets. Part of the indictment says that in addition to shipping flyers, they shipped laptops from Miami to St Louis. Either they wanted a really interactive flyer or they were helping BOS set up wagering stations around the U.S.
ESPN takes ads, maxim takes ads, I believe Playboy takes ads, Trader Mag takes ads, I believe the NYT and most newspapers have taken ads. IF the DOJ wanted to take down advertising, therx would not top the list (Sorry rx we love you, but the NYT and ESPN have you beat!)
I took down my site a little bit for fear of legal problems, but mostly because I was meeting with a venture capital firm about another business and they did not want it up.
Saying that you can not advertise a sportbook online which is legal to 90% of the world is like saying you can not advertise a resort that provides hookers or a bar that provides drugs in a country where these things are legal. I do not think that is a battle the DOJ wants to take on. The DOJ got what they wanted - yahoo and aol and google backed down. Google and yahoo are 90% of the internets searches. If the DOJ were to take this on, it would go to court and a judge would have to decide if this is constitutional free speech. IF the DOJ lost, google and yahoo would have gambling ads back online in 10 minutes.
-Sean