I suppose it's possible. Heck, the U.S. air defense grid would have plenty of holes in it after the TDM. On the other hand, just a pair of fully armed F-15 could wipe out an entire airfleet of Soviet/Cuban transport aircraft. The Soviets don't have any true fleet carriers and Cuba's airforce is somewhat limited in its size and long-range capability so I don't see an airlift having much in the way of fighter cover. Where would it come from? Without it, an airdrop that far behind enemy lines wouldn't stand much of a chance if it was detected. How many U.S. airbases (non-nuked) would such an airlift (originating in Cuba, I would assume) have to bypass undetected? That's quite a long shot.
But hey, if it works for your T2K universe, go for it.
Wolverines!
