City on a Hill Review: The Night Flynn Sent the Cops on the Ice (Season 1 Episode 1)
A bird’s eye view of Boston in the 1990’s becomes the focus on City on a Hill Season 1 Episode 1, “The Night Flynn Sent the Cops on the Ice.”
Its starting point comes in trying to protect an FBI informant source from getting charged in a police shooting, while armored truck robberies start occurring and become a larger focus by episode’s end.
The show is more or less a co-starring affair between Aldis Hodge’s district attorney Decourcy Ward and Kevin Bacon’s FBI agent Jackie Rohr. Both could not be any different from each other, one a man of the law while the other skirts it any way he can.

Bacon looks to be having the time of his life as Jackie, this slippery person of circumstance whose life is completely off the rails. He’s smirking and smiling and cursing his way through every scene, and a complete joy to watch. Jackie’s not without his use, too, offering Decourcy the way to properly solving the armored truck situation.
The show smartly pits Decourcy against a world of injustice, where the law is malleable in lieu of favors and expediency. His heart is too much in the right place, believing in justice and doing the right thing. It’s a tall order, to stand among a pit of snakes and attempt to bend them to your will, but his perseverance, and willingness to use that very system against itself at the end, makes for an interesting avenue to take his character down.
Taking down a corrupt system from the inside has certainly been done before on other series, but City on a Hill attempts to do a wide-angle view of the entire system, rather than focus on one individual piece. It’s a little like HBO’s The Wire in this way, where each piece when zoomed out tells a larger and more potent story, as great as those pieces by themselves are, as well.

At the street level is Jonathan Tucker’s Frankie and his crew, robbing armored trucks for a currently undisclosed reason. Frankie mentions to his wife Cathy that the first truck’s haul is not enough, as though there’s a benefactor he’s working toward paying off, or they’re looking for a way out from it all. It will be interesting to see what he’s building towards, if not for himself and his family.
His brother Jimmy looks to be his weak link, desperate for cash and unable to keep his need for money straight. He’s a loose cannon, and going up against his brother Frankie’s wrath will prove an explosive move. Frankie, when confronted with bribing the still-alive armored security, decides to murder them rather than give up chump change from the robbery to save them. He’s all in on this, and wants no loose ends.
There’s a lot going on during the pilot: armored truck robberies by Frankie’s crew, Jackie attempting to coerce his informant’s release, Decourcy trying to avoid that very informant’s release, and on top of it all, their personal lives and mentions of past deeds and misdeeds.
It’s a rather elaborate web, made more elaborate by the reveal at the end of Jimmy, Frankie’s brother, being an informant for Jackie, which could prove to blow the whole armored truck case wide open just as it’s beginning. And to the show’s credit, the intricate storytelling never bogs down or gets too complicated.

The show does a great job of setting its season up, placing the pieces down so the conflict is clear and central to what comes next. It’s a world full of prejudices and near-impossible odds to face, but it’s done with a can-do attitude of pushing through, brute force, to get results.
City on a Hill Season 1 Episode 1, “The Night Flynn Sent the Cops on the Ice,” finds a lot of its success through such strongly defined characters. Personalities are overflowing from each and every member of the cast, their performers left with plenty to work with to become memorable and have their times to shine.
The pilot is a solid starting point, offering strong personality and context to a city brimming with possibility, finding itself in need of someone like Decourcy to wake it from its more questionable tendencies.
What did you think of this episode of City on a Hill? Share your thoughts in the comments below!
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City on a Hill airs Sundays at 9/8c on Showtime.
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