As Jesus went on from there, he saw a man named Matthew sitting at the tax collector's booth. "Follow me," he told him, and Matthew got up and followed him.
Although this little verse seems straightforward, there is more going on than at first meets the eye. There is a back-story, a cultural backdrop, and probably more actual dialog than recorded. Since the full conversation wasn't recorded, we don't know exactly what was said, but if we fill in some of the cultural details, we can imagine what was going on.
Matthew was Jewish. He was Jewish, working for the Roman Empire -he collected taxes. His position wasn't assigned, it was bought; he had purchased the right to collect taxes. When we say "collect taxes," don't think along the lines of IRS policies and tax laws, because, frankly, Rome didn't care exactly how a tax collector got his money as long as he turned in the amount he had agreed to when he purchased the right to be the regional tax collector. Anything the tax collector collected over and above what Rome demanded was his to keep. An ambitious tax collector could become very wealthy.
Of course, there was a trade-off. Tax collectors became wealthy, but they were despised and they were ex-communicated from the temple. Rome was the oppressor. Collecting from fellow citizens for Rome was treachery.
Because they had the backing of Rome and very few regulations as to how to do their jobs, tax collectors tended to collect as much as they could get away with without the local citizens actually murdering them. Typically they set up a booth on a major road near a town and taxed everyone coming and going. They could tax for anything they wanted. They taxed people for anything going to market. They taxed people for anything they had purchased at market. They taxed people for conducting business. They taxed for anything that they could think of to tax someone for. It was legalized extortion.
Jesus and His disciples came across Matthew's tax booth. Since we know that Jesus actually talked to Matthew, it is safe to assume that Matthew had stopped them and was trying to figure how much to tax them. Matthew was sizing them up trying to discern how much money they had. he probably asked them some questions. And I imagine that as Jesus answered the questions patiently and kindly, He gave Matthew a sense of dignity that Matthew hadn't felt from anyone in a long, long time. Jesus wasn't hateful. Jesus wasn't angry.
Whatever other questions got asked, eventually Jesus looked deeply into Matthew's eyes and asked, "Matthew, why don't you leave all of this behind and follow me?"
And, amazingly, Matthew did. Whatever the conversation actually was, Matthew felt from Jesus a compassion and a kindness and a sense of self-worth, a hope for a brand new start that caused him to leave his tax-booth, to leave his profession, to walk away from everything he was and everything he had and evrything he knew and begin a new life following Jesus.
I believe the invitation Jesus gave Matthew is the same invitation He gives us. "Leave your old life -leave your old habits and dreams and ways of thinking -just walk away, and follow Me."
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