I'd describe CHICAGO SYNDICATE as average but entertaining. The story is reasonably engrossing, there are nice supporting turns by Abbe Lane and Paul Stewart, and there's also some terrific Chicago location work.
Mobster Arnie Valent (Stewart) orders a hit on his bookkeeper, who is going to inform on Valent to law enforcement, and the man is gunned down on the street. The cops turn to Barry Amsterdam (O'Keefe), an accountant with a military background, to go undercover and get the goods on Valent.
To Barry's dismay, Valent destroys key incriminating papers after showing them to Barry, but Barry later learns that Valent's mistress, Connie (Lane), has them on microfilm as "insurance."
Meanwhile the dead accountant's daughter Joyce (Allison Hayes) has been working undercover herself, posing as a woman named Sue Morton. Sue comes on to Valent, trying to make Connie jealous and angry enough to threaten to disclose the location of the microfilm.
This is a fast-paced 83-minute movie directed by Fred F. Sears. It's done in classic docu-noir style, with the voice of an omniscient narrator (Richard Cutting) filling in the blanks as Barry works his way up through Valent's organization.
There's also a lot of great footage shot in Chicago, with the final confrontation between Barry and Valent making especially good use of locations. The movie was filmed in black and white by Fred Jackman Jr. and Henry Freulich.
Abbe Lane does a good job with a flashy role as Valent's spurned mistress, a singer with a drinking problem. "Benny Chico," the leader of the band who backs her, is played by Xavier Cugat, who was Lane's husband at the time. I'm not sure I've seen Cugat in a film before where he was anything other than "Cugie." The music, with Lane singing "One at a Time," also adds to enjoyment of the movie.
CHICAGO SYNDICATE isn't the best of the genre or the best of O'Keefe's noir titles, but those who share my enjoyment of the actor and this type of film should find it worthwhile.
HOLD THAT KISS (1938), ARISE, MY LOVE (1940), THE LEOPARD MAN (1943), MR. DISTRICT ATTORNEY (1947), DISHONORED LADY (1947), T-MEN (1947) WALK A CROOKED MILE (1948), RAW DEAL (1948), ABANDONED (1949), COVER UP (1949), WOMAN ON THE RUN (1950), THE COMPANY SHE KEEPS (1951), THE FAKE (1953), THE DIAMOND WIZARD (1954), and LAS VEGAS SHAKEDOWN (1955).
I also spotted Dennis O'Keefe in bit or extra roles in DEATH ON THE DIAMOND (1934), 13 HOURS BY AIR (1936), COLLEEN (1936), SWING HIGH, SWING LOW (1937), and BETWEEN TWO WOMEN (1937).