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Because this film starred Dennis O'Keefe (who was wonderful in his Film Noir appearances), I was sure to see it. And fortunately, the overall effort was exciting and engaging--making it a decent later example of the genre. While not as bloody and earthy as many Noir films, due to the head of the mob priding himself on being a well-spoken gentleman, nevertheless is a decent film of this type.

The film begins with a contract killing so stop an accountant from spilling his guts about organized crime. A citizen's group decides that they need to try a new way to infiltrate the mob--send in a freelance agent who isn't a cop or part of the Treasury or Justice Departments. So Dennis O'Keefe is recruited and he is able to eventually rise very high in the ranks--and leading to a wonderful showdown.

I think the reason I like O'Keefe in these films is because he's so ugly--or at best ordinary looking. For Noir, this is great, as pretty boys and the like are NOT something you'd expect. So, when Edmund O'Brien isn't available, O'Keefe is a good substitute.

Full of excellent intrigue, an interesting and unusual plot and sure to please fans of the genre, CHICAGO SYNDICATE nearly earns an 8--it's that good.

FYI--It is interesting that in one scene where they are standing outside a movie theater, the picture listed on the marquee is ON THE WATERFRONT--another film about mobsters which came out at about the same time as CHICAGO SYNDICATE.

I saw the show on Turner Classic Movies. The plot was entertaining. It kicks off with a murder of a mob accountant who gave inside info to a newspaper man (the "Syndicate" didn't like that.) The newsman then gets some leading Chicago people plus lawmen together to try to "break the Syndicate wide open." They persuade Barry Amsterdam (Dennis O'Keefe), an aspiring accountant dreaming of starting his own business, to infiltrate the mob and get the lowdown on the crooks. He ends up doing an amazing job, for an accountant! But the use of real street scenes is what made this a very interesting movie for a Chicago history buff like me. You can see many downtown locations (theaters, buildings, bridges, rivers, street signs), era shots (men in hats, big cars, 50s trains & buses) and dialog about real places (Halsted, Ohio, The Palmer House, Maxwell Street). Lot's of fun!

Dennis O'Keefe plays Barry Amersterdam, an accountant hired by authorities to infiltrate the syndicate in order the get the goods on the top man Arnie Valent. He works his way in and soon rises to become the mobs top accountant. Along the way he is distracted by Joyce Kern (Allison Hayes) a women out to avenge the mob murder of her father. CHICAGO SYNDICATE is a standard "B" crime thriller of the period. It is one of many films made in the fifties purporting to expose the sin, crime, corruption and vice of some major American city. Dennis O'Keefe gives his usual breezy performance. Allison Hayes is sexy. The best performance is Paul Stewart as mob boss Arnie Valent. Stewart was always at his best when he played slimy crooks, and he is quite convincing here as the nasty mob boss who loves his mother and likes to beat women.

There's little in the late noir Chicago Syndicate that hadn't already been done, and more memorably, in the cycle, but, given the limitations of its director and cast, it does its job. When a renegade syndicate bookkeeper is gunned down on a crowded street in broad daylight (incidentally triggering his wife's suicide), federal agents enlist Dennis O'Keefe, a forensic accountant working for the police, to infiltrate the underworld. In no time he's won the trust of boss Paul Stewart (whose start in movies was in Citizen Kane, as Raymond the sinister butler). Stewart idolizes his mother, who refuses to budge from his tough old neighborhood. But apparently she's the exception that tests his misogynistic rule (`Everything gets better with age, except women,' he observes).

He's right to be wary, because women hold the tools to destroy him. His current trophy (Abbe Lane), who sings with bandleader Xavier Cugat in mob night spots, drinks too much and endures humiliation and beatings at his hands. But even an attempt to `scare the girdle off her' fails, as she holds incriminating microfilm, stashed away as her insurance policy. Her rival for his attentions (Allison Hayes) has a secret agenda: she's the orphaned daughter of the slain bookkeeper, nursing a vendetta. When she thinks O'Keefe can grease her way to the top, she throws herself at him (`Now you're romancing me like I was Liberace,' he puzzlingly tells her.) She becomes his helpmate – and decoy.

In the style of the syndicate movies of the 1950s, in the wake of the Kefauver hearings on organized crime, there's an emphasis on the complex corporate structure of Stewart's illegal business operations. Too much exposition, however, is left to voice-over narration. And while the movie doesn't shy away from ugly incident, it's quite devoid of the atmospheric dread that distinguished, for instance, Fritz Lang's The Big Heat. O'Keefe, too, seems to have aged more than the eight years separating this movie from his similar role in Anthony Mann's T-Men, making it less of a surprise that his first movie role was in 1930. Chicago Syndicate holds interest less for its own sake than as evidence of how the noir cycle was running down, if not quite out; the same year offered Joseph H. Lewis' brilliant take on much the same territory, The Big Combo.

Nothing happens in this rather bleak and sordid noir about Chicago gangsters, until Alison Hayes pulls the gun in the middle of the film, and then the action starts, amounting to rather interesting proportions. Dennis O'Keefe is no William Holden, who would have been the right actor for this role - Dennis is too fidgety. Paul Stewart on the other hand is perfect for his character, and the other ladies are good as well, Abbe Lane as the night club primadonna in decline with a catch on the boss, and his mother. The best scenes are with these women, while it is Alison Hayes who runs the show from half way on. The finale approaches the depths of "The Third Man".

So although you yawn and look for something else to do meanwhile during the first half of the film, the second half must have all your attention. The dialog is riveting and splendid all the way, even Xavier Cugat gets a role to play and not only instruments, so it's after all a film well worth seeing.