Luke chapter fifteen begins with a bunch of publicans and sinners gathering around Jesus to hear him teach. When you look at the context in which this event occurs it is indeed interesting. Jesus had just delivered a very pointed and demanding gospel message. Cf. Luke 14:25-35. The lost were not put off by this message but it seems were rather attracted by it. It seems to me that we ought to give more credit to the lost. They know that truth is ridged and demanding. Any attempt to ease up on the demands of the Gospel only cause them to question the truth and the motives of those who deliver such a “cheapened” message.
Jesus had a huge compassion for the lost but it did not cause Him to ease up on the demands of the Gospel. A Gospel that does not bring a broken heart and humility is not a true Gospel at all. That is the reason that our Lord follows this with the story of the prodigal son. The prodigal son came home with a broken heart. We are moved to love that lost son because of his honesty and humility. That is the “straight” gate that must be entered through. The word “straight” in the Gospel refers to difficult and demanding. To enter by some other gate, is to not enter at all.