The president has decided to start normalizing relations with Cuba. A communist pariah nation (not it's people) with waning support from Russia and Venezuela which is in rough shape and subject to more concessions on democracy that could be extracted from it's Castro leadership right now than the president cares to try to get.
There's no strategic value in this. There's little political value in this - Cubans in America are not likely to support the president on this and Hispanics in general are also unlikely to be moved more towards the president. Is it perhaps a scorched earth policy towards Hillary Clinton and her presidential aspirations? I doubt it. It seems like a purely ideological move, proving the president is indeed progressive and algned with a very left leaning world view.
How does this serve America in any way? Will Cuba suddenly become more democratic? Renounce communism? NO.
Did the president come before the American people and explain why this is happening and spell out the reasons for it? NO.
For those reasons this is without merit and just plain dumb.