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Message: <blockquote data-quote="Calico_Jack73" data-source="post: 1353688" data-attributes="member: 14403">Magic Missile always hits so there is no chance to miss and hit the person being grappled.  A 9th level caster will be dishing out 5d4+5 per Magic Missile.  If the caster has one quickened Magic Missile then you've got 10d4+10 damage in one round that the Monk can' escape.  Personally, I think illusions are the way to beat the guy.  Mirror Image is a great one since he won't know which image to attack and will have to rely on luck.  Use Major Image to give him a bogus enemy to attack.  He won't get a Will saving throw until he has some reason to disbelieve it (pg 173 DMG).  The Freedom of Movement spell will render someone "Un-Grapple-Able".  Even a 5th level Wizard can cast Gaseous Form to escape from your Monk.  All he'd have to do is take a 5' step back and cast Gaseous Form and he would'nt take an attack of opportunity.  SO... it seems like a 7th level wizard is your answer.  Go into battle with Freedom of Movement cast (4th level spell) or just have the wizard use the Fly spell to stay out of the Monk's reach... even a 5th level wizard can do that.If you REALLY want to be mean, let him grapple a high level Druid who promptly Wild Shapes into a Dire Bear.  Let him try to grapple that!</blockquote>