What is Magdi'el?
Rashi and Targum Yonasan: Magdi'el 1 is synonymous with Rome.
Ramban: It was the name of a powerful nation, the likes of which had never been seen before.
Which is the acronym of 'Migdal El' (a strong tower [Peirush Yonasan]), or, as the Pasuk writes in Daniel, "he will aggrandize himself over all the powers (Yisgadel Al Kol El)" (Daniel 11:36) - [Ramban; but see his objection to Rashi's explanation (refer to 36:40:3:1*). Even though the Midrash (in Pirkei d'R. Eliezer) refers to Magdi'el as Rome, this is merely in the form of a hint ('Ma'aseh Avos Siman l'Banim'). Refer to 36:40:1:3*.] See also Sifsei Chachamim.
What is the significance of the name "Iram"?
Ramban: Iram is merely an extension of Magdiel, who will prepare stores of treasures (la'Arom Tisoriyos) for King Mashi'ach. 1
Gur Aryeh: "Iram" (lit. meaning "their city") is also referring to Rome. 2 Rome is thus described as an "Ir" (city) and a "Migdal" (tower) reaching the Heavens [Gur Aryeh is drawing a parallel between Rome and the Tower of Bavel described in Bereishis 11:4. 3 ] Ultimately, Hashem will descend to judge Rome as well; and then He will rebuild His holy city Yerushalayim, with its Tower of David.
Rabeinu Bechayei adds that the word Iram has the same letters as "mi'Ya'ar" (Tehilim 80:14), which fits that Pasuk's description of Esav as a boar, and as the word "me'Ir" (Bamidbar 24:19), which refers to Rome. Indeed, the 'Ayin' in "mi'Ya'ar" (Tehilim ibid.) is hanging, leaving the letters 'Romi.'
Pirkei d'Rebbi Eliezer, Ch. 38.
Rome also strove to raise themselves up to the heavens, and wage war against Hashem (as implied by the name Magdi'el). (EK) See Daniel 11:36; refer to 36:43:1:1*.
Why does the Torah write, "Hu Esav Avi Edom"?
Megilah 11a: Esav is in his wickedness from beginning to end.
QUESTIONS ON RASHI
Rashi writes: "Magdi'el - This is Rome." How do we know this word can even be expounded? (Perhaps it is just a name!)
Gur Aryeh: There is not always necessarily rhyme or reason in a name. But here the name "Magdi'el" means "Hashem aggrandizes it;" and we should therefore expound the reason.
Rashi writes: "Magdi'el - This is Rome." How is this implied in the verse?
Gur Aryeh: "Magdi'el" means 'Hashem aggrandizes it;' and "Romi" (in Leshon Kodesh) also means 'loftiness.'
Rashi writes: "Magdi'el - This is Rome." But many kings would rule over Rome, not just one?
Gur Aryeh: See Rashi to 36:40. These chieftains were not names of individuals or even families, but rather of localities belonging to Esav. Many kings would rule in succession over the one locality named Magdi'el / Rome.
Rashi writes: "Magdi'el - This is Rome." But Rome was a great empire; would the Torah call it a mere 'chieftainhood'?!
Gur Aryeh: Rome was not always an empire; the Torah refers to it only by the status it would have always.
Rashi writes: "Magdi'el - This is Rome." What is the implication of the name 'Rome'?
Gur Aryeh: Hashem aggrandized Rome, 1 giving them sovereignty. Magdi'el / Rome is the tenth 2 and most important among Esav's chief localities.
Maharal (Gevuros Hashem Ch. 8, p. 48): Although Rome would appear to have greatness, with world-wide fame and influence, it would have no inherent greatness of its own, only what it expropriated or stole from other [nations]. Perhaps Maharal is implying this here in Gur Aryeh as well. (EK)