Gambling online is very much legal for the players, the U.S. has tried to control banks from transfering money to online sites, but these sites have come up with different transaction options. Some sites stopped accepting U.S. players once this bill was passed but many sites still accept U.S. players.
Betfair.com offers a free $25 bet to all new users and their odds are higher than most as they are a gambling exchange and so do not take commission.
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Yes. Many illegal immigrants play the lottery, and when they win they usually ask a legal friend to cash out the money for them. They do this because they don't want to risk deportation, although it's totally legal for them to cash it out themselves even with an illegal status.
The general answer is, no, but it depends on what specific context you are referring to.