No. A tip pooling arrangement can be legal but it must exclude certain types of employees (usually managers who are purely salaried).  You need to review DC's tip pooling laws under the FLSA and see if there is a specific exclusion for such employees. Usually front of house and back of house will share (like clean up staff).  In terms of the manager using the sale of wine as a backwards method of getting in on the pool is absolutely ridiculous, runs afoul of many labor laws and can and will cause a conflict of interest in terms of scheduling shifts amongst the serving staff, bartending staff and the like so he can possibly get a higher cut. Do your research first and then approach the labor board or if you have the gumption, the corporate office of this restaurant.