I think he'd like the new Winchester Model 70 Classic Sporter & the sporter laminates. I think Jack would also like the Ruger Hawkeye as they are built like a rifle should be. I suspect he would probably go with the 270, 30-06, and 280 Remington. These are classics that haven't really been improved upon!! I think he might seriously consider the new 270 WSM or 300 WSM in addition to that though. For scopes it would be a 4x or 6x Leupold or possibly a 2.5-8x36 Leupold.

Now for bullets old Jack would shoot the beloved Partition which is still the standard, and the new Nosler Accubond or E-tip.

David