Well, maybe He wasn't meek in the way we usually define the term.
Jesus didn't pull any punches with some folks.
He echoed his late cousin John when He called some Pharisees "you brood of vipers" - once in Matthew 12 (v. 34) and once in Matthew 23. In the latter tirade, He also called them "blind guides," "hypocrites" and "fools."
But look at the reasons why He called them by such epithets. And think about who they were: the religious leaders. The ones who should have known God's will, but knew only their own rules. They were the very people who should have practiced what they preached; should have been good examples to others; should have been opening the door for others to get closer to God, rather than shutting it in their faces and refusing to go in themselves.
Do we do that?
When we dress up nicely for church and sing of giving our best to the Master and make the poor visitor among us feel ashamed and unworthy?
When we make rules out of the way we see God's word and insist that others observe them, but have no intention of following them ourselves?
When we major in the minors of giving to maintain our opulent places of worship, but neglect mercy and faithfuless and (social) justice?
Do I do that?
Ouch. Ouch. Ouch.