Jesus was an itinerant preacher, and said similar things on many different occasions. On one occasion he gave a long sermon “on a mountainside,” which Matthew records as the Sermon on the Mount. On another occasion, he gave a shorter sermon “on a level place,” which Luke records as the so-called Sermon on the Plain. The two sermons are similar, but there are noticeable differences, including the series of “woes” that only Luke includes:
24 “But woe to you who are rich,Luke 6:24-26
for you have already received your comfort.
25 Woe to you who are well fed now,
for you will go hungry.
Woe to you who laugh now,
for you will mourn and weep.
26 Woe to you when everyone speaks well of you,
for that is how their ancestors treated the false prophets.”
I think the key to understanding what Jesus is getting at here is to think of the blessings and the woes in the Sermon on the Plain as commentary on what Jesus will later tell his disciples:
23 Then he said to them all: “Whoever wants to be my disciple must deny themselves and take up their cross daily and follow me. 24 For whoever wants to save their life will lose it, but whoever loses their life for me will save it. 25 What good is it for someone to gain the whole world, and yet lose or forfeit their very self?Luke 9:23-25
In other words, if what you have keeps you from following Jesus and receiving eternal life, it would be better to have nothing; if you have nothing, but you are Jesus’s disciple, then it means you have everything that matters.
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