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A taildragger is an aircraft whose undercarriage consists of (usually) two main wheels forward of the center of gravity, and a small wheel or skid to support the tail.

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Has there ever been a tail-dragger with retractable tail-gear?

Yes, there are. The Boeing B-17 FLying Fortress is one example of an aircraft designed with a retractable tailwheel. Source: USAAF via Wikimedia, Public Domain (USGOV-PD) Another example would be t …
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