Magdiel, Iram, and Romi
Who is Magdiel and Who is Iram?
The last Rashi on Vayishlah is on the Pasuk אלוף מגדיאל - Rashi adds זו רומי. This tells us that Magdiel is Rome. See the Ramban and the Mefarshei Rashi here (including the באר בשדה, who says that this רומי refers to "the small Rome". See R' Gil Student's post for a possible explanation).
Midrash Rabba and Yalkut Shimoni bring down the following:
אלוף מגדיאל אלוף עירם יום שמלך לוטינוס נראה לר' אמי בחלום היום מלך מגדיאל. אמר עוד מלך אחד נתבקש לאדום אלוף עירם למה נקרא שמו עירם שהוא עתיד לערום תסבריות למלך המשיח. מעשה בשלטון אחד שהיה מבזבז תסבריות של אביו נראה לו אליהו ז"ל בחלום וא"ל אבותיך מצמצמין ואתה מבזבז ולא זז עד שמלאן.
The Chief of Magdiel, the chief of Iram - From the day that the king Lotinus began his reign, the following appeared to Rabbi Ami in a dream: "Today Magdiel has reigned". He [Rabbi Ami] said, "One more king is sought for Edom." The chief of Iram - Why was he called Iram? Because he is destined to empty out his treasury [to give to] the King Mashiah. There was an incident with one [Roman] ruler who was wasting the treasury of his father. Eliyahu, Zachur Latov, appeared to him in a dream, and told him, "Your forefathers were storing, and you are wasting?" [He did so so that the Mashiah will gain more eventually. - Etz Yosef] The ruler didn't move from there until he refilled his treasury [by blackmailing his constituants - Etz Yosef].
It would appear from this Midrash, then, that Iram was a separate king (nation?) that will live right before the coming of Mashiah.
Rabbeinu Bahye, however, takes a different approach. He says that when the Torah said "Chief of Iram", it is merely explaining Magdiel. In other words, the Torah is saying "Magdiel, who is the Chief of Iram." Iram is spelled עירם, which (besides meaning "their city" of Rome) are the same letters as מיער - from the verse in Tehillim יכרסמנה חזיר מיער. Notice on the above link that the letter "ע" of the word מיער is raised to indicate that it can be removed to give you the letters רמי, or Romi. The חזיר, pig, is the fourth of the beasts that was in Daniel's prophecy, which is to symbolize the fourth exile of Edom, or Romi. Iram also has the same letters as מעיר as from the verse in Bil'am's prophecy וְיֵרְדְּ, מִיַּעֲקֹב; וְהֶאֱבִיד שָׂרִיד, מֵעִיר which is speaking of Edom at the end of days.
So, we have 2 different explanations on Iram. However, either way, we pray that the following verse that Sephardic Jews read in the Haftara this week will come speedily, in our days:
וְעָלוּ מוֹשִׁעִים בְּהַר צִיּוֹן, לִשְׁפֹּט אֶת-הַר עֵשָׂו; וְהָיְתָה לַיהוָה, הַמְּלוּכָה