A friend bought a bottle of this down in TN. We tasted it tonight beside an Angelo Luchessi to see if there is any difference since they are both 90 proof. From what we were told and read the Sinatra barrel had grooves cut into the barrels to give the whiskey more surface area to interact with. These barrels were then mingled with regular Jack barrels. The SS definitely had a bigger flavor to it than the Luchessi. It had the Jack flavor but amplified more. Some char some burn and a little vanilla mixed in. A long finish. The Luchessi was similar but not as in your face. There isn't any of the nuttiness or maple syrup of the Single Barrel or Silver Select. This is pretty good stuff and stands out above regular Jack for sure but definitely not worth $150. I'm glad I didn't buy it but also glad I got to try it