Have you ever heard of the 1976 Goof’s Pants Place Tulsa Oilers team set? After posting Q&A – What Is The First Pack-Inserted Autographed Card? this set was brought to my attention thanks to Breakout Cards and Chris Harris as it contains a few autographs.
In 1976 the Tulsa Oilers (Triple-A affiliate of the St. Louis Cardinals) released a 26-card team set which could be purchased from the team for $5. Included within that team set were two autographed cards – Satchel Paige and Paul “Daffy” Dean.


Both of these cards predate the Reggie Jackson autographed card issued by Upper Deck by 14 years.
Personally, I still consider the 1990 Upper Deck Baseball High Series Reggie Jackson Auto #’ed/2,500 the first pack-inserted autographed card. The 1976 Goof’s Pants Place Tulsa Oilers team set was a regional issue, and not made available everywhere. A hobby pack, and team set are two different things.
Sports Collectors Daily has a nice write-up about this set.
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