I reached double-digit deals with Sam from The Daily Dimwit fame as we recently competed our tenth trade. You can see the first here, second here, third here, fourth here, fifth here, sixth here, seventh here, eighth here, and ninth here.
The bulk of the deal was a near-complete set of 2015 Allen & Ginter. Sam sent 348 of the 350 Base + SPs (or theoretical SPs this year, I suppose). I already had the Yasiel Puig base and Sam was without one other base random dude (#97) so I'm only one card short!