BTW, I was originally against introducing .timestamp() method and this issue illustrates why it is problematic: people use it without understanding what it does.  If you want the distance between datetime.min and datetime(1970,1,1) in seconds - compute it explicitly:

>>> (datetime.min - datetime(1970,1,1)) / timedelta(0, 1)
-62135596800.0

If you don't want to loose precision is roundtriping between datetimes and numbers - use microseconds:

>>> (datetime.min - datetime(1970,1,1)) // datetime.resolution
-62135596800000000

It is perfectly fine to work with naive datetimes and ignore the timezone issues when all your timestamps are in one timezones, but if you choose to ignore timezones - don't use .timestamp().