“Why do you eat with ‘sinners’?”

Read Luke 5:27-32

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Levi was also known as Matthew (Mt.9:9).  Tax-collectors were notorious for their dishonesty, and thus very unpopular. So for Jesus to enlist Levi among his disciples surprised many people (including the other disciples!) Luke adds that Levi, “left everything” (28; 5:11). It was a brave step to take. “If following Jesus had not worked out for the fishermen, they could have returned to their trade. But when Levi walked out of his job, it was a final commitment” (Morris). 

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But the main point of this story is the further confrontation with the Pharisees and the teachers of the law (29-30). In their eyes some people were obviously 'sinners' e.g. the sexually immoral (Lk.7:37-39), Sabbath-breakers (Jn. 9:16), Gentiles (Gal. 2:15), and tax-collectors. (Lk.15:1-2; 19:7). Anyone who ate with them would be ceremonially defiled (Jn.18:28). 

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But that didn’t bother Jesus – what mattered to him was mission to people most in need of God’s help (31). It was not that he condoned their sin, for he came to call “sinners to repentance” (32). To do that, he had to get alongside them and be their friend. Love and mercy, not 'religion', are what God most requires (Mt.9:13; Hos.6:6).