I'd separate them and let them out different times. Ignore his whining. Do you have another place to put him like maybe a different room or garage? My pup was dominant and was always picking on my older dog. I rotate them for free time. When they do play together, it's only for short periods of time and always supervised. I correct by grabbing the back neck and shake with a firm "phooie" (not crazy shake but just so she snaps out of it). I take control of the situation and do not allow it ever. She's changed and plays nicely now. If your pup goes back at it, correct him again. He will eventually get it if you are consistent and firm.
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