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Passing very flexible guards is difficult, period. When the guard player can invert, monitor, replace and defend with lots of dynamic flexibility, you are likely to have a hard time securing the pass. This video shows some principles, techniques and tricks for dealing with this kind of flexible guard, no gi edition. Obviously, lots of other ways exist for dealing with this, but these are just a few I selected to illustrate so principles I think are important. I hope this helps.
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