That's the picture from the Doom of Daggerdale module. According to the adventure backstory, the Zhentarim wrested control of the Dagger Falls from him "50 years ago", and the adventure is set in 1368, so that would have happened in 1318. The FRCS says that he was overthrown "nearly 30" years ago (from 1372), making it about 1342, and that he retook lordship 3 years ago (in 1369).
That may also be him on the cover of the Doom of Daggerdale module. You can find plenty of examples by doing a google image search for the module's name.
I think there was a picture of him in one of the 2e books from the 2e boxed set. Not the grey boxed set. That picture above might be from the booklet "running the realms" IIRC.