NO LONGER AVAILABLE Listing ended Oct 5, 2026

1958 Pontiac Chieftain

$45,995

Vehicle Details

Make

Pontiac

Model

Chieftain

Year

1958

VIN

AMS35956

Body Type

Wagon

Transmission

Automatic

Engine

6.1 V8 240hp

Description

1958 Pontiac Chieftain Safari Wagon. Ready to take the family on a road trip? In Style! This is an incredibly rare '58 Pontiac wagon, completely original; when's the last time you've seen one?! This wagon features the original 240hp 6.1 V8 & 'Super Hydra-Matic' transmission. The power steering makes this car turn on a dime! The pictures speak for themselves.

Pontiac Chieftain Buyer's Guide

Full guide

Mike Sullivan

Muscle Cars

1949–1958

~3 min read

Updated Apr 2026

The Pontiac Chieftain defined the brand's identity through one of the most turbulent decades in American automotive history, surviving the transition from straight-eight to V8 power, from Silver Streak styling to the new Strato-Streak era, and from postwar austerity to the chrome excess of the late 1950s.

This guide covers

✓ 8-point inspection checklist

✓ Common issues & what to avoid

✓ In-person inspection guide

✓ Market pricing by year & condition

✓ 4 FAQs answered

✓ History & fun facts

Read the Full Chieftain Buyer's Guide

Pontiac Chieftain Market Overview

Based on 15 Pontiac Chieftain listings currently on ClassicCarsArena.com

Listed Now

$27,289

Avg. Asking Price

1938–1957

Year Range

Price Position on Our Site - Above Average

This car: $45,995

Low: $4,495 High: $72,995

Transmission Distribution

Automatic 73% ◄

Condition Distribution

Excellent 13%

Good 7%

Fair 7%

Data from ClassicCarsArena.com listings Browse all 15 listings →

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Pontiac Chieftain Buyer's Guide

Mike Sullivan here. The Pontiac Chieftain doesn't get the collector attention it deserves, and I think it comes down to positioning. Pontiac sat between Chevrolet and Oldsmobile in the General Motors hierarchy, not cheap enough to be ubiquitous, not expensive enough to be prestigious. But the Chieftain from 1955 through 1958 is a genuinely good car: the new Strato-Streak V8, the wide-body proportions, and a driving experience that outclasses what the price suggested. When Bunkie Knudsen arrived at Pontiac in 1956 and started the performance-first overhaul that would produce the GTO a decade later, the Chieftain was what he had to work with.

The pre-V8 Chieftains (1949–1954) are a different story, important to marque completists, good-looking cars, but powered by the inline-eight that Pontiac needed to replace. The real collector argument for the Chieftain starts in 1955.

What to Check Before Buying

✓

Rear Quarter Rust , Check rear quarter panels, primary rust location on all Chieftains in any climate.

✓

Lower Front Fenders , Probe where fender meets rocker panel, consistent rust point on all postwar Pontiacs.

✓

Straight-Eight Condition (1949–54) , Compression test on straight-eight, verify even cylinders and no oil consumption smoke.

✓

Tri-Power Sync (1957–58) , All three carburetors must idle and transition smoothly, rough running indicates sync issues.

✓

Hydra-Matic Function , Test all selector positions, smooth shifts with no slipping or harsh engagements.

✓

Hardtop Body Rigidity , On Catalina hardtops, check door gaps for even alignment, body twist from improper storage is common.

✓

Chrome Completeness (1958) , Inventory all exterior chrome on 1958 cars, replacement pieces are difficult to source correctly.

✓

V8 Date Codes (performance cars) , On Tri-Power cars, verify engine date codes match car production date, transplanted engines reduce value.

Common Issues

Rear quarter panel rust on salt-belt cars from any era. Lower front fender rust where the fender meets the rocker. Straight-eight oil consumption on high-mileage unrestored 1949–1954 examples. Hydra-Matic seal leaks and fluid contamination. Tri-Power carburetor synchronization issues, all three carbs must be properly tuned. 1958 chrome trim deterioration and difficult-to-source replacements. Hardtop body twist on cars stored improperly. Power window circuit failures on luxury-optioned cars.

What to Look For

On 1949–1954 straight-eight cars, inspect the frame rails and lower body sections, these are 70+ year old vehicles. The straight-eight engine is reliable but check for oil consumption and head gasket condition. On 1955–1958 V8 cars, inspect the rear quarter panels and lower front fenders for rust, standard salt-belt locations. The Tri-Power carburetor setup on 1957–1958 cars requires all three carburetors to be properly synchronized, a cold start and smooth progression to full throttle verifies basic function. Verify the Hydra-Matic transmission operates through all ranges without slipping. On Catalina hardtop body styles, inspect the door and roof structure for any flex or misalignment from body twist.

Price Guide

1949–1954 Chieftain straight-eight (sedan driver): $8,000–$18,000. 1949–1954 Chieftain Catalina hardtop: $14,000–$28,000. 1955 Chieftain V8 (first-year): $12,000–$25,000. 1956–1957 Chieftain V8 (sedan): $10,000–$22,000. 1957 Chieftain Tri-Power 347ci (documented): $22,000–$42,000. 1958 Chieftain Tri-Power (370ci): $18,000–$38,000. Convertibles in any year add 40–60% over equivalent hardtop prices.

Did You Know?

The Pontiac Chieftain name was retired after 1958, the same year Bunkie Knudsen's performance program was beginning to produce results. Two years after the Chieftain ended, Pontiac introduced the Wide-Track design philosophy; four years later, the Tempest offered the GTO option that created the muscle car category. The Silver Streak chrome strips that defined early Pontiacs were such a long-running tradition (introduced in 1935) that Pontiac used them as a marketing identity even as they became styling anachronisms in the early 1950s, they were finally abandoned with the 1957 redesign.

$45,995