I would say use a 4" stroke crank, .030 over bore, ported heads, tripower and ram air exhaust manifolds, 450hp would be easy.
Basically building a 421 out of your 389.
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66 GTO Nostalgia Super Stock/Street Legal Car
421 CID, stock block, Wenzler Intake, 2- Carter 750 AFB's, 3.90 Gears, Full Factory Interior, Full Exhaust, Stock Suspension 3750LBS 9.77@136.99
Multiple NSCA/NMCA World Champion
66 GTO 389 3x2, 4 speed, 4.33 gear, Montero Red 33K original Miles
67 GTO 2dr Post, 428, Tri Power, 3.55 Gears
80 Trans Am Black SE Y84 W72 WS6
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