Summary: The feeding stories are very familiar. The basic point of the passage should not be lost: Jesus has compassion on people and feeds them. We are called, in spite of obstacles, to do likewise. That said, there are some beautiful wrinkles in the Greek that will hopefully open up your imagination for preaching!
κατά ιδιον (meaning "by himself", 14:13) After hearing the news of Herod and John, Jesus is probably feeling many emotions. For the first time in the Gospel, Jesus wants to go off by himself. Matthew really emphasizes how much Jesus wants to get away: by himself, in the wilderness, in a boat.
σπλαγχνισθη (from σπλαγχνιζομαι, meaning "compassion", 14:14) Jesus has compassion -- which in Greek literally reads "Jesus intestine someone." The word for compassion in Greek is intestines because when you have compassion your stomach turns over. The nature of Jesus is on full display -- grieving he wants to be alone, yet seeing the crowd his guts churn. You can decide whether this is the human or divine in Jesus...or both!
θεραπεω (therapeo, meaning "heal", 14:14) I've written about the word therapy elsewhere, but I simply want to point out today the link between therapy and compassion. Jesus desire to do therapy arises out of his compassion. In spite of the fact that Jesus is exhausted, his compassion moves not simply his mind, his heart, or even his intestines, but his whole body. Sometimes we get to move into ministry from a position of strength. Sometimes we are called into ministry when depleted. (By ministry I don't just mean ordained ministry, but the call to minister given to all Christians)
απολυσον (from απολυω, meaning "release", 14:15) The disciples ask Jesus to "release" or apoluoo the people. Perhaps a haunting question: Do you think the disciples are worried about Jesus needing rest, the crowd needing food or them needing an emotional and physical break from the people? I suggest the later... Sadly, they want to send the people back to the place where they came from, to the city. Frankly, I empathize with the disciples here. The task of ministry can be overwhelming.
δοτε (aorist form of δίδωμι, meaning "give", 14:16): In this case, the verb δοτε is in the aorist. This is the same tense of the verb that is used in the Lord's prayer, "Give us this day." Jesus taught his disciples to pray to God to give them their daily bread. Now he commands them to give others daily bread. The aorist form of the verb also provides insight. The aorist tense suggests a one time event. Jesus is not asking the disciples to worry about the crowd's consistent daily needs, simply to worry about this one night. Perhaps this suggests that the disciples, in their worry about future provision, are forgetting their task is in the present.
ουκ ("no" or "not", 14:17) The disciples response to Jesus begins with the word no and reveals their sense of scarcity. They focus on what they do not have. [Grammar note: the word ουκ ends in κ because it comes before a vowel]
φερετε...αυτους ("carry them", 14:18) Okay...I am going out on a limb here. The Greek here literally reads, "Carry them to me." Normally we assume that Jesus is referring to the bread and the fish. Which is probably true. But I was struck by the fact that the next motion in the passage involves the people. Perhaps Jesus is telling the disciples: "Bring the people to me." This opens up a few sermon possibilities: First, that our purpose is always to bring people to Christ; second, that Jesus believes the crowd has more and that once they come close they will actually be moved to share..."
λαβων ευλογησεν κλασας εδωκεν ( take, bless, broke and gave, 14:19) These words appear again in Matthew 26:26, when Jesus is hosting the last supper/first Holy Communion.
[missing word here, 14:19. The disciples now give the food to the crowd; however, the verb give is missing. It literally reads "The disciples (to) the crowds." Maybe the disciples also took the bread and broke it and give it...and not just gave it!
εχορτασθησαν (from χορταζω, meaning "to fill", 14:20) The word here for "fill" is related to the word for grass -- the crowd sat on the grass "chortos" and later was "chortazo"-ed. Perhaps a subtle reminder that God's abundance is always there -- even in the midst of a "herma" (wilderness, vs 13; and 15) and when the "oora" (hour) has past (vs 15).