RFC 2001 says
Since TCP does not know whether a duplicate ACK is caused by a lost
segment or just a reordering of segments, it waits for a small number
of duplicate ACKs to be received. It is assumed that if there is
just a reordering of the segments, there will be only one or two
duplicate ACKs before the reordered segment is processed, which will
then generate a new ACK. If three or more duplicate ACKs are
received in a row, it is a strong indication that a segment has been
lost. TCP then performs a retransmission of what appears to be the
missing segment, without waiting for a retransmission timer to
expire.
The reasoning for not doing the retransmit until the third duplicate seems to be that until that point it's more likely to just be out-of-order delivery and the retransmit isn't really needed.
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