‘City on a Hill’ Review: Is the 1990’s Boston Crime Drama Worth Your Time?

Take a look at our review for ‘City on a Hill’, the new Showtime series set in 1990’s Boston pitting a dogged prosecutor and a corrupt FBI agent against a gang of armored truck robbers…

By Damon Martin — Editor/Lead Writer

The opening moments of Showtime’s new crime-drama series ‘City on a Hill’ really sets the stage for what unravels over the next 60 minutes.

In 1989, a man named Chuck Stuart and his wife were accosted and shot on their way home in an apparent car jacking. Chuck’s pregnant wife was killed and their baby died days later after being born prematurely. Chuck was shot in the stomach but survived and later claimed that a black man was responsible for the shootings.

A citywide manhunt ensued with cops urged to do anything possible to bring this criminal to justice. As the card opening the debut episode reads “during the investigation, the Boston Police Department used intimidation and coercion, eventually charging a black man”.

Chuck Stuard identified the black man in a line up and the city was prepared to try and convict this man of some truly heinous crimes. There was only one problem — the accused criminal didn’t shoot Chuck Stuart or his wife.

It turns out, Chuck plotted this entire murder himself with help from his younger brother, who eventually ratted him out. Chuck was going after insurance money that would have gone to him in the event of his wife’s death. Before police could arrest him, Chuck committed suicide and his younger brother ended up spending five years behind bars.

Sadly, the destruction of what Chuck Stuart set in motion lasted for several years as Boston faced serious racial tension in the middle of a city already ravaged by crime.

This is where our story kicks off as we meet corrupt FBI agent Jackie Rohr, who once played a part in bringing down a mafia family in Boston and now he’s living off the fruits of that labor for pretty much everything else he’s done since then. His counterpart on the series is an ambitious prosecutor from the District Attorney’s office named Decourcy Ward, who came to prominence after he put a bunch of cops in jail while working as a U.S. District Attorney. Unfortunately after having his wings clipped in several attempts to keep cleaning up law enforcement, Ward decides to move into the city of Boston and take a shot from the inside out.

The third component in this series is played by Jonathan Tucker, who portrays armored car robber Frankie Ryan. In the daytime hours, Frankie stocks grocery shelves and cares for his wife and family but when it’s time to bring some extra cash home, he partners up with some local friends and they take down armored cars.

When the debut episode begins, Frankie and his crew are about to hit another armored car when things go terribly wrong. In the midst of the robbery, one of the guards decides to go after the criminals and he gets shot dead. The other two guards see the face of one of Frankie’s crew, which means they are a few mugshots away from identifying the entire crew.

That forces Frankie to make a difficult decision as he opts to kill the guards, dump their bodies and hope nobody ever finds them. Frankie is simultaneously dealing with family drama as his junkie brother keeps finding new and creative ways to get in trouble with the cops but he wants to do right by him so he brings him home and eventually allows him to join his crew on the next robbery.

As for Ward, he tries his best to do the right thing but he keeps running into all sorts of obstacles until he finally decides that playing within the system might be the only way he’s going to ever truly make changes to Boston. When the case about the armored truck robbery comes across his table, he’s told to pass because nobody in the neighborhood of Charlestown will ever turn on one of their own so it’s not even worth the investigation.

That’s exactly what convinces Ward to go after these armored truck robbers and he partners up with Jackie to get the FBI on board and use his years of expertise scheming within the system to get the job done.

The debut episode that dropped on Showtime on Sunday night feels like a lot of pilots in that it sets up the story for what’s to follow but doesn’t give away too much. There is one notable exception when it comes to ‘City on a Hill’ and that’s a stunning revelation that’s made in the closing moments that gives you an idea of what to expect during this 10 episode run.

The series has Ben Affleck and Matt Damon on board as executive producers because those two guys have always enjoyed stories that take place in their native Boston from “Good Will Hunting” to “The Town”, which is the film that will ring in your head constantly while watching “City on a Hill”.

Affleck even said that part of the reason why he wanted to get involved with “City on a Hill” was because he had so much research done on the bank robbery business that sprung out of Charlestown that he almost felt bad not finding a way to explore it deeper. That appears to be the goal of this series as we’re seeing both sides of the battle with the cops and a dogged prosecutor on one side and a family of armored car robbers on the other.

“City on a Hill” does a good job displaying the kind of grimy feel that had to resonate throughout the Boston at a time when criminals like James “Whitey” Bulger seemingly had more power than the police or the politicians. It’s a city teetering on the brink — and the tipping point could force the citizens to fight to take back Boston or the entire place could just dissolve into chaos.

Kevin Bacon, who plays FBI Agent Jackie Rohr has the sleazy FED routine down pat — and the reality is there’s not much Kevin Bacon can’t play well at this point in his legendary career. Aldis Hodge plays prosecutor Decourcy Ward and he does an admirable job holding his own against an award winner like Bacon without ever really giving him an inch when both are chewing scenery. The final component and perhaps the best part of the series through a single episode is Jonathan Tucker as complicated armored car robber Frankie Ryan.

It’s already evident that Frankie is going to be the tragic figure in this series much like watching Ben Affleck’s character Doug McCray try desperately to escape his life in “The Town” only to constantly watch himself get pulled back into it. Frankie is a family man and his devotion to his wife and kids is admirable, which makes him a likeable character even if he’s supposed to be the bad guy.

When it comes to morally compromised characters, Frankie is the one you’ll root for even if he’s doing bad things and Jackie is the cop you’ll love to hate. In the middle sits Decourcy Ward and he’ll end up serving as the moral compass on this series.

Overall, the first episode was highly watchable —  plenty of cutting dialogue with that pitch perfect Boston accent that really sells the neighborhoods where this story takes place. The plot is easy enough to follow while setting the stage for the rest of the season as Ward and Jackie aim to bring down these armored car robbers and Frankie is doing his best to feed his family on the fortune he steals for them.

If you enjoy films like “The Town” or “Den of Thieves” or maybe even a series such as “The Wire” then “City on a Hill” will be worth your time. It will take time to see if the whole season can surpass the pilot, which is absolutely necessary if the show will get renewed but so far it’s enough that I’m setting up a DVR recording for 9 p.m. every Sunday night on Showtime.

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