By Dennis Hartley

(Originally posted on Digby’s Hullabaloo on May 19, 2007)

If spending an evening with the CIA is your idea of good times, have I got a double bill for you. (Break out the hoods and the water buckets; we’re in for a bumpy night!)

First up, Robert De Niro takes the director’s chair in his 2006 CIA epic, The Good Shepherd, recently released on DVD. Matt Damon stars as Edward Wilson, whose career as an agency spook begins with his enlistment into the OSS during WW 2 and continues through that organization’s metamorphosis into the CIA.

The film opens in 1961, at the time of the Bay of Pigs invasion. When we are first introduced to Wilson, it is quickly established that he is an officious and dedicated Company man. As the story begins to jump back and forth in time we begin to get a peek at what lies beneath Wilson’s somewhat inscrutable veneer.

We witness a looser and more outgoing Wilson during his college days at Yale in 1939, as he is inducted into the infamous Skull and Bones society. As part of the initiation ritual, he is directed to regale his fellow Bondsmen with the deepest, darkest secret from his past. The club members get more than they bargain for as Wilson relates a harrowing childhood memory of bearing witness to his father’s suicide. Moments before taking his own life, his father hands down a credo about “trust”, which becomes the key to unlocking Wilson’s motivations and inner workings for the remainder of the film.

Therein lays the problem with The Good Shepherd. There is an awful lot of internalizing going on (for 2 hours and 47 minutes). De Niro’s plus as a director (not surprisingly) is his willingness to give his actors plenty of room to breathe and inhabit their characters. His minus as a director is his willingness to give his actors plenty of room to breathe and inhabit their characters, if you catch my drift. There are some pacing issues with the film. Not that I was expecting car chases and stuff blowing up real good. After all, the reality of espionage does not necessarily lend itself to flash cuts and pop music montage. It’s generally a somewhat somber, mundane and unpleasant business.

Eric Roth’s script has its moments, but gets murky when it comes to the intrigue. It is tough to keep track of who is doing what to whom, and why (and at times, for whose “side”?). Granted, perhaps that is part of the point; torture is torture and murder is murder, no matter how one attempts to rationalize (a point that Steven Spielberg more than sufficiently bludgeoned us over the head with in Munich) but I GET it, already.

Perhaps the most fatal flaw in the film is Matt Damon’s unconvincing “aging”. There is not much discernible physical transformation between Wilson’s collegiate years and middle age. (Maybe some better prosthetic work could have helped?). At any rate, I just wasn’t buying it, and found it to be a major distraction. Damon is a fine actor, but I think he may have been slightly miscast here. History buffs may still find the film worth a look.

History buffs (and conspiracy-a-go-go enthusiasts) will definitely want a peek at British director Dolan Cannell’s documentary, 638 Ways to Kill Castro (just out on DVD). Mixing archival footage with some knowledgeable talking heads (including a surprising number of would-be assassins-it’s hard to believe this many lived to tell their tale!), Cannell traces the evolution of Cuban politics via a recap of literally hundreds of attempts by the U.S. government to knock off Fidel over the years.

The number in the title (638) is derived from a list compiled by a couple of former members of Castro’s security team (they are among the interviewees). They even go so far as to crunch the numbers by U.S. presidential administration. In case you’re curious, here’s the breakdown (aren’t you glad I take notes?): Eisenhower-38 attempts. Kennedy-42. Johnson-72. Nixon-184. Carter-64. Reagan-197 (Ding Ding! We have a winner!). Bush (the 1st)-16. Clinton-21. (We assume they haven’t had a chance to tally the latest Bush’s numbers, although Cannell slyly bookends his film with footage of Junior’s smug and condescending “Cuba libre!” proclamation.)

The film begins its timeline in 1959, the year that the CIA received the first official go-ahead to take Castro out. The initial schemes sound like they were hatched by Wile E. Coyote and his Acme Intelligence Agency. The plans ranged from relatively benign subversion (making his beard fall out, spraying a TV station with LSD while Castro was on air, a contingency to accuse Cuba of zapping John Glenn’s space capsule with “magnetic rays,” had Glenn not made it back to Earth) to more ominous (a poisoned diving suit, booby trapping shellfish in Castro’s favorite scuba diving spot with dynamite, and most famously, planting poisoned and/or exploding cigars into his humidor).

Although Cannell initially appears to be playing for yucks (especially with the exploding cigar type shtick) the underlying theme of the documentary soon becomes much more sobering. The most chilling revelation concerns the downing of a commercial Cuban airliner off of Barbados in 1976 (73 people were killed, none with any known direct associations with the Castro regime). One of the alleged masterminds was an anti-Castro Cuban exile living in Florida, named Orlando Bosch, who had participated in numerous CIA-backed actions in the past.

When Bosch was threatened with deportation in the late 80’s, a number of Republicans rallied to have him pardoned, including Florida congresswoman Ileana Ross, who used her involvement with the “Free Orlando Bosch” campaign as part of her running platform. Her campaign manager was a young up and coming politician named…Jeb Bush. Long story short? Then-president George Bush Sr. ended up granting Bosch a pardon in 1990. BTW, Bosch had once been publicly referred to as an “unrepentant terrorist” by the Attorney General. (Don’t get me started.)

This is a fascinating film; the only criticism I would give it is the director’s “wacky” approach (that kooky CIA and their nutty ideas!)-it doesn’t quite match the subject matter at times. My favorite quote from the doc sums it all up quite nicely-when asked to explain the decades-long obsession about Castro by one administration after another, one pundit cracks “There’s just something about (Castro’s) Cuba that affects these administrations like the full moon affects a werewolf. There’s no real logic at work here.”