How should the U.S. government go about securing the release of Alan Gross, a Jewish American development contractor convicted in Cuba of illegally distributing sophisticated telecommunications equipment to the Cuban Jewish community as part of USAID's democracy building program?  Having exhausted all his legal options - Cuba's Supreme Court declined on Friday to overturn his 15 year sentence - Mr. Gross will be stuck in Cuba unless and until Raul Castro decides to give him a humanitarian release.

Should the U.S. heed the advice of the Miami Herald and Jerusalem Post editorial boards, and reverse recently loosened travel restrictions, until Havana releases Gross?  Or should it instead make an overture - a serious, legitimately courageous one - as Tim Padgett suggests in a Time magazine blog post, and finally remove Cuba from the State Department's terrorism list, for which there has long been scant evidence?

It's understandable that there are those who feel a man is sitting in prison for what wouldn't really be a crime anywhere else; well, except for the fact that most countries do expect visitors to properly declare the purpose of their visits and the equipment they are carrying, and to obtain licenses to operate telecommunications equipment.  These are domains regulated (if not so tightly controlled as in Cuba) by governments.  And though the Post and Herald gloss over this key issue, Mr. Gross's work was contracted under a law specifically designed to help hasten the end of the present Cuban government.  Nonetheless, there's no doubt that the punishment doesn't nearly fit the crime.  [Cuban authorities are quick to point out that this sounds a lot like their Cuban Five, who were given especially long prison sentences here in the United States for what the Cuban government considers to be heroic infilration of militant anti-Castro groups and their supporters in South Florida.]

So, if you believe that the Cuban government should release Alan Gross, because the punishment doesn't fit the crime, and 20 months have passed since he first landed in jail, why not reach for the stick now?  It might make some folks feel better - to inflict some pain in return - but it absolutely will not bring Alan Gross one iota closer to his family.  Have we learned nothing from half a century of U.S. sanctions on Cuba?  They simply don't work, and if anything, Havana only digs in deeper when the U.S. tightens the screws.  Moreover, and importantly, the U.S. travel restrictions in question are too often viewed first as a concession to Havana, when they should really be seen as a restoration of rights to the American people, who are free to travel to any country in the world except for Cuba.  Is it really appropriate to trade the rights of millions of Americans in this or any other case?

Now, reaching for the carrot, on the other hand, seems equally tempting.  What might happen if Goliath finally reached out to David?  Would David put down the slingshot?  Maybe.  But maybe not.  The hard truth is that almost no one knows what Cuba wants, or if it wants anything at all, in exchange for Alan Gross's freedom.  After decades of mistrust, cynicism and moved goal posts, of near encounters and colossal last minute setbacks, and after more than 2 years of slow-walking baby steps from an American president who boldly called the old policy a failure, I'm not sure that one gesture alone could build the kind of good will we're talking about here. 

Granted, Tim Padgett's got a bold idea.  Short of ending the regime change program that landed Alan Gross in Havana in the first place, delisting Havana from the terrorism list is the best hope for the U.S. to show good faith in its policy.  I'm not suggesting that the Obama administration cozy up and invite the Castros to dinner.  It's about whether there's a real policy in place or merely domestic politics at play.  If the State Department finally cleaned up its terrorism list (hello, Libya and North Korea were de-listed by George Bush - this shouldn't be that hard a nut to crack!) and stuck to real hard facts, it doesn't have to give up its stand on greater freedoms for Cubans.  It just means a return to accountability.  And even though Havana would still grouse at continuing U.S. criticisms over its human rights record, Cuba's leaders, who are 1000% convinced that U.S. policy is bought and paid for by a minority in the Cuban American community, would sit up and take notice.

I'll agree with the Jerusalem Post that we owe it to Alan Gross to act.  Considering the U.S. government essentially sent Alan Gross into hostile territory with no plan for what might happen to him if Cuban authorities caught up to him, it's time to reconsider a prime way to influence Havana to release him.  But reversing course on people to people and family travel would harm Americans and American values, not to mention the Cuban people, as much or more than it would harm the Cuban government, and it would likely backfire.   It's time to make a trade without trading: fix a widely discredited terrorism list by removing Cuba (or at least softening the language used to include it on the list) while sending a message to Havana that we're serious.  Short of that, it's just a waiting and hoping game to see if Raul Castro offers Gross clemency for its own sake.