Brad, awesome save by cosmic and can see why that one would mean a lot as well.
This truly is a difficult decision but from a purely historic point of view it would be this Dunhill Bruyere Churchwarden with 14k hallmarked band and original marked case.
From an artistic point of view it would be one of these Calabash pipes by Trever Talbert, Davorin Denovic and Altinook collaboration, one by Maigurs Knets or the 2 bowled one by Mimmo Provenzano.
Or one of these two Morta pipes, the first a 9 1/2" Morta Cutty by Chris Askwith, the second the late Paulo Becker's Maya desnuda, hope I never have to pick since it would mean deciding what tobacco to save as well!
banjo