Okay, sorry if this was covered a long long time ago, but it's kinda popped up and I don't remember the ruling.

Say I have U Prometheus, who is a wildcard with outwit.

Can he wildcard Superman Enemy and have two outwits?

If that is the case, can he also use ICWO, with Oracle on the card, so that he could have 3 Outwits? Thusly, outwitting 3 different people at the same time?

This doesn't sound right to me, but I can't find the ruling for it. Thanks in advance for any/all help!

I unfortunately can't direct you to the documentation, but a character can only have one Outwit at a time.

Clixer11 is correct. You can't double up on the same power. Not only that, but let's say hypothetically that someone outwits your outwit that is on your figure's dial. You can't even use something like ICWO or Anti-Supes TA to regain the power. It remains outwitted regardless of whether the source of that power changes.

You can, however, double or even triple up on different powers in the same slot. For example, Owlman + ICWO can give you Outwit (on the dial), Perplex (from Oracle), and Probability Control (from the TA) all at the same time

The updated DC Team Abilities sheet states that if a Superman Enemy figure already has Outwit, then the team ability has no effect. Under the updated DC HeroClix Errata and Clarification, it specifically states that if an agent is given a power action to turn Oracle's dial to a specific power that is already shown on the agent, then power gained from Oracle will have no effect as well.