The command to rebuild Jerusalem and its temple starts the seventy sets of seven. The event that best matches this is Cyrus the Great's decree in 538 BC, which allowed the Jews to return to Jerusalem and start rebuilding (see Daniel 5:31; 9:1; Ezra 1:2–4). Less likely are the decrees of Artaxerxes I in 458 BC (see Ezra 7:12–26) and 445 BC (see Nehemiah 2:5–8).
the Messiah, the Prince: Many interpreters believe Christ fulfills this prophecy, viewing this passage as covering history from Daniel's time to Christ's time.
However, a Messiah can refer to any of Israel’s kings or priests, who were anointed with oil. If fulfilled during Antiochus IV's time, the anointed one was likely the high priest then, Onias III (compare Daniel 11:22).
a trench: The vision describes Jerusalem being physically rebuilt. The Jews finished rebuilding the temple's in 515 BC (Ezra 3:1–6:22). In 445 BC, Nehemiah completed Jerusalem's wall (Nehemiah 2–6).
The times of distress may refer to Jerusalem and its temple's history from the decree's publication until the end of the seventy sets of seven (see Daniel 11:2–45).