Steiff Teddy Girl
Maker: Steiff
Original Price: Unknown*
Worth Today: $171,600*
This particular bear was made in 1905 and was a gift to a newborn Bob Henderson. The bear accompanied the British Army Colonel to war and survived the D-Day landings in 1962. Henderson went on to found Good Bears of the World which provides teddies for sick children. After his passing in 1990, the beloved Steiff bear sold at auction for $171,000 setting a world record for the most expensive teddy bear.