Summary: John wants to know whether Jesus is the Messiah, because it doesn’t seem that the gospel he’s proclaiming is good news. But it is!
I guess everyone has some idea what we mean when we talk about the gospel. But I wonder what your preferred translation of that word would be.
Is Good News the correct translation do you think? Is the gospel necessarily good news? You may never have thought about that question, but if you do think about it, you’ll realise that how you answer it affects how you’ll present the gospel to people.
You see if it’s just good news, then the way you present the gospel will be to tell people all the benefits that it brings, but to gloss over the negative side of the message. That is, what happens if you choose to reject it. The danger of that, of course, is that it can result in the message being trivialised, so that Jesus is presented like some sort of spiritual aspirin or pep-pill.
It’s a bit like that old riddle: "When is a key not a key?" Answer: "When it’s a donkey." Well, the passage that we have before us today from Luke 7 (quickview)  raises the question, "When is the good news not good news?" It speaks of the gospel as good news for the poor, but as we read on we discover that for some it’s bad news. Why? Because it’s a gospel about a new Kingdom and those who reject its King will in turn find themselves rejected.
When is the good news not good news? When it’s about a new King that you don’t want as your King or a Kingdom that doesn’t fit your preconceived ideas about it.
The passage begins with John the Baptist sending two of his disciples to ask Jesus whether he’s the one they were expecting.
You see, for John, the gospel that Jesus was preaching seemed like bad news. John’s expectation was of a Messiah who’d come to cleanse Israel of its sin. He expected a Messiah who’d restore the kingdom to its former glory.
Mind you, he may have been expecting the gospel to result in good news, but even his presentation of it didn’t sound too good for some.
Listen to what we find John saying in Luke 3 (quickview) : "You brood of vipers! Who warned you to flee from the wrath to come? 8Bear fruits worthy of repentance. ... Even now the ax is lying at the root of the trees; every tree therefore that does not bear good fruit is cut down and thrown into the fire." ... 16"I baptize you with water; but one who is more powerful than I is coming; ... He will baptize you with the Holy Spirit and fire. 17His winnowing fork is in his hand, to clear his threshing floor and to gather the wheat into his granary; but the chaff he will burn with unquenchable fire." (Luke 3:7-17 (quickview)  NRSV)
So John had actually announced a Messiah who’d bring wrath and destruction, fire and judgement. The fire that he’d bring would be a cleansing fire to prepare Israel to be God’s Kingdom once again.
But now John has been arrested by Herod because of his preaching of the need for repentance. So as he sat in Herod’s dungeon he must have started to wonder why Jesus hadn’t responded by bringing down judgement on Herod and rescuing him. He was beginning to wonder whether perhaps he’d got it wrong. The gospel that Jesus preached didn’t seem like the sort of good news he’d expected.