Simultaneous Interpretation (SI) is quite a pressurizing cognitive process per se. Media Interpretation (MI) is more coercing being processed remotely without paralinguistic aiding factors. Lingua cultural challenges, like allusions make an interpreter's task even more pressing. References to public figures, historical events, fictional characters, cultural aspects or proverbial clichés call for associations that go beyond mere substitution. Leppihalme (1997) categorization of allusions is adopted in the present study [allusions proper (noun phrase and key phrase) and stereotyped allusions]. The source discourse (SD) is 19 of Obama's speeches interpreted into Arabic by various TV channels, like Al- Jazeera and Al-Ghad. Being a celebrated orator keen on public support, Obama resorts to using cultural, historical, religious and national allusions that have specific connotations shared by members of his cultural community. Riccardi's (2005) interpretive strategies of production and emergency are employed to examine how interpreters transfer different allusion types into the target discourse (TD). The most frequently used strategy is omission (35.7%) due to cognitive and time constraints. Interpreters resort to morphosyntactic transformation (21.4%) in an attempt to render an accurate, acceptable equivalent. The least frequently employed strategies are expansion and approximation as the SI interpreter does not have the time or cognitive capacity for adding linguistic units or rendering a close meaning without hitting on the exact substitution. Generalization, transcoding and compression are also employed. Strategies, which involve inventing variant TD message like Parallel reformulation, are used, however in few emergency cases. MI interpreters employ strategies to achieve accuracy, comprehensibility and acceptance.