Did Benjamin Sisko underestimate Garak on Star Trek: Deep Space Nine?

Did Benjamin Sisko underestimate Garak during Star Trek: Deep Space Nine’s “In the Pale Moonlight”?

Often considered one of the best yet darkest points in Star Trek: Deep Space Nine, if not the entire franchise, “In the Pale Moonlight” pushed Captain Benjamin Sisko to his limit as he ended up breaking his own moral code to turn the tide of the Dominion War and possibly save millions of lives.  To do this, he asks Garak to help him bring the Romulans into the war and as a consequence, a Romulan politician was killed.

While Sisko did not personally kill Senator Vreenak, he did enlist Garak to help bring the Romulans into the war and Garak’s actions kill Vreenak, thus Sisko has some culpability in Vreenak’s death.  The ethical questions about this facet of “In the Pale Moonlight” could fill volumes, but something that often gets overlooked is whether Sisko underestimated Garak.

Fans may now joke about “plain simple Garak” being a cunning and manipulative spy who should never be underestimated, but Sisko does not have as much hindsight as the audience does and his previous interactions with Garak may not have provided enough information.  Sisko did use Garak’s skill set before to outwit Gowron, yet that incident did not lead to a politician being murdered and Garak’s own faked assassination plot on himself never led to anyone’s direct death.

Benjamin Sisko may have gotten the wrong impression from  past encounters, so he underestimated Garak during “In the Pale Moonlight”

Sisko had used Garak’s spy past before in the episode “The Way of the Warrior”.  A Klingon fleet under Gowron’s command is in the Alpha Quadrant and even though the reason given is they are there to protect the Alpha Quadrant, Sisko does not believe this, so he enlists Worf to check out Gowron’s story.  Garak comes into play when Worf gives his report to Sisko.  Sisko calls Garak under the pretext of measuring him for a new suit, but has Worf read and discuss the report so that Garak can then report the true reason behind Gowron’s fleet to Gul Dukat.

Based on the outcome of this experience, Sisko may not have foreseen Vreenak’s death “In the Pale Moonlight” as Garak is able to pass on the information to Dukat and forces Gowron to reveal his real mission.  Sisko’s actions are forced by the Klingons themselves and he has them on record lying about their presence in the Alpha Quadrant.  He merely revealed the truth so that Starfleet could take the appropriate actions.

One of Garak’s most manipulative actions, faking an assassination attempt on himself, possibly inspired Sisko to further utilize his skills during “In the Pale Moonlight” because those events proved Garak could manipulate others around him while not killing others.  In the episode, “Improbable Cause” Garak blows up his own tailor shop and incriminates an assassin disguised as a perfume maker.  When Odo confronts the ‘perfumer’ it turns out he was sent to assassinate Garak, yet the assassin was going to use a combination of scents to poison Garak who used various factors, including unique chemicals, to implicate the assassin.

Herein lies the central issue – there was an assassin going after Garak, he merely implicated the assassin before the actual assassination attempt could take place.  Sisko may have imagined when he hired Garak to help him bring the Romulans into the Dominion War that he would do something similar – manipulate the facts just enough to bring the Romulans into the war – while not taking a life.  At first glance, the data rod created by a master Klingon forger appears to be the perfect thing to convince the Romulans to join the Federation and Klingons against the Dominion, based on real data and information, just spun in a certain way.  Yet Vreenak is able to tell the data rod is fake which seals his fate.