Verse 26: Condemned persons normally carried their own crosses (technically, just the horizontal beam of the cross) out to the site of their execution. Here, however, someone else is drafted; Roman soldiers could draft bystanders to carry things for them (see comment on Matt 5:41).
Cyrene in North Africa had a massive Jewish community (as well as Greek and indigenous residents); many Jewish people used the name “Simon” (which resembled the patriarchal name “Simeon”). Jewish pilgrims (and presumably a few God-fearers) came from throughout the Empire for Passover. (Given the Passover context, when work would be forbidden, Simon cannot be “coming from the field” because he was working there; Jerusalem was so full of pilgrims that many had to seek lodging in surrounding villages.)
27: Authorities derived propaganda value from public executions, and crowds normally turned up to view them. Although official public mourning (as at a funeral service) was forbidden for a condemned person, no one would stop women from mourning in the streets. Women were expected to express lamentation more freely and dramatically than men, and they were less subject to public punishment. (Later rabbinic tradition claims that Jerusalem’s pious women offered a narcotic drink to dull the pain of the person being executed.)
28: “Daughters of Jerusalem” naturally enough refers to Jerusalem’s women, but might also recall some OT judgment oracles (for example, Isaiah 3:16). “Mourn for yourselves” also recalls judgment oracles (e.g., Isaiah 32:9-14; Joel 1:5).
29: Other Jewish sources use similar language for the lament a mother would utter when her children died. During the siege of Jerusalem a generation later, Josephus reports that some women became so hungry that they ate their children (cf. Deut 28:53).
30: Jesus recalls here OT judgment oracles (Hoseah 10:8; Isaiah 2:10, 19-21).
31: Dry wood would catch fire much more easily than green wood. This could mean that if Rome reacted thus to Jesus, how much more would they punish genuine revolutionaries? Or that if Jerusalem’s leaders treated Jesus this way, how much greater would be the violence against genuine threats (Jewish people fought each other as well as Romans in 66-70)? Or it could simply indicate that Jerusalem is becoming more ripe for judgment (cf. Luke 21:24, 29-30).
32: Authorities preferred to execute people on festivals, when the executions would warn the greatest number of people against rebellion. Executing several prisoners at once also simplified the soldiers’ duties.
(Adapted from Dr. Keener’s personal research. Used with permission from InterVarsity Press, which published similar research by Dr. Keener in The IVP Bible Background Commentary: New Testament. Buy the book here.)