| Issue | #52 |
| Published | September 1944 |
| Cover Price | 0.10 USD |
| Pages | 52 |
| Editing | ? |
| Notes | Indicia title is "LITTLE ORPHAN ANNIE, No. 52." No code number. Copyright 1938 by Chicago Tribune-N.Y. News Syndicate, Inc. |
| Characters | Little Orphan Annie; Sandy (dog) |
| Characters | Little Orphan Annie; Sandy (dog); Rose Chance; Ace Chance; Shanghai; Mrs. Alden; Bindle Al |
| Synopsis | Rose Chance's husband Ace steals money from his wife's business in order to gamble. In a high-stakes poker game Ace shoots a pro gambler and is arrested. |
| Script | Harold Gray (signed) |
| Pencils | Harold Gray (signed) |
| Inks | Harold Gray (signed) |
| Notes | Story begins on the inside front cover in black, red, and white. |
| Reprinted | from Little Orphan Annie (News-Tribune Syndicate) newspaper strips from 1938 |
| Characters | Little Orphan Annie; Sandy (dog); Ace Chance; Rose Chance; Shanghai; Jack |
| Synopsis | Jack, who's secretly in love with Rose Chance, goes to great lengths to make sure that the man Ace Chance shot lives and that Ace will get good legal defense. |
| Script | Harold Gray (signed) |
| Pencils | Harold Gray (signed) |
| Inks | Harold Gray (signed) |
| Notes | The dates are on the strips. |
| Reprinted | from Little Orphan Annie (News-Tribune Syndicate) daily newspaper strips from 1938.07.02, 1938.07.04-1938.07.09, 1938.07.11-1938.07.15 |
| Characters | Little Orphan Annie (cameo); Ace Chance; Rose Chance (cameo); Jack; Bindle Al |
| Synopsis | Jack and Ace get into a brawl, which Jack wins. Ace goes to work as a manual laborer for Jack's trucking company. Bindle Al comes to talk to Jack. |
| Script | Harold Gray (signed) |
| Pencils | Harold Gray (signed) |
| Inks | Harold Gray (signed) |
| Notes | Dates are on the strips. |
| Reprinted | from Little Orphan Annie (News-Tribune Syndicate) newspaper strips from 1938.07.16, 1938.07.17, 1938.07.21-1938.07.24 |
| Characters | Little Orphan Annie; Sandy (dog); Ace Chance; Mary Chance; Jack; Shanghai |
| Synopsis | A truck axle falls on Ace's foot, smashing it. During his recovery, Jack makes him the bookkeeper and Ace has to fight temptation when dealing with cash. |
| Script | Harold Gray (signed) |
| Pencils | Harold Gray (signed) |
| Inks | Harold Gray (signed) |
| Reprinted | from Little Orphan Annie (News-Tribune Syndicate) newspaper strips from 1938 |
| Characters | Little Orphan Annie; Sandy (dog); Ace Chance; Mrs. Alden; Rose Chance; Jack; Shanghai |
| Synopsis | Ace is accused of theft when Jack's company's office is robbed; but Jack stands behind him and the real robber is picked up by the police. |
| Script | Harold Gray (signed) |
| Pencils | Harold Gray (signed) |
| Inks | Harold Gray (signed) |
| Reprinted | from Little Orphan Annie (News-Tribune Syndicate) newspaper strips from 1938 |
| Characters | Little Orphan Annie; Sandy (dog); Ace Chance; Rose Chance; Shanghai; Mrs. Alden; Jack; Uriah Gudge |
| Synopsis | A random comment by Ace Chance about something he saw 30 years ago in Springfield sets Annie and Shanghai investigating whether it has any connection to the death of Mrs. Alden's husband then. Uriah Gudge sets up a trucking company to take Jack's business--by fair means or foul. |
| Script | Harold Gray |
| Pencils | Harold Gray |
| Inks | Harold Gray |
| Reprinted | from Little Orphan Annie (News-Tribune Syndicate) newspaper strips from 1938 |
| Characters | Little Orphan Annie; Sandy (dog); Shanghai; Uriah Gudge; Jack; Ace Chance; Rose Chance; Mrs. Alden (cameo) |
| Synopsis | Jack sets a trap for Gudge's murderous truckers. After one of Gudge's trucks crashes off a high bridge, Gudge meets Ace Chance to see if he can buy information. Ace pretends to go along with Gudge, but has plans of his own. |
| Script | Harold Gray |
| Pencils | Harold Gray |
| Inks | Harold Gray |
| Reprinted | from Little Orphan Annie (News-Tribune Syndicate) newspaper strips from 1938 |
| Characters | Little Orphan Annie; Sandy (dog); Uriah Gudge; Jack; Shanghai; Ace Chance; Mrs. Alden; |
| Synopsis | Ace appears to betray Jack to Gudge. Gudge sets up a plan to hijack a half-million dollar load on the road and kill Jack at the same time. Ace drugs Jack and drives the truck himself. He crushes the thugs' car with his truck but is killed by their machine gun fire. Gudge disappears mysteriously and Shanghai busies himself filling in an old well in the orchard. |
| Script | Harold Gray (signed) |
| Pencils | Harold Gray (signed) |
| Inks | Harold Gray (signed) |
| Notes | Dates are on some, but not all of the strips. |
| Reprinted | from Little Orphan Annie (News-Tribune Syndicate) newspaper strips from 1938.09.22-1938.10.17? |
| Characters | Little Orphan Annie; Sandy (dog); Jack; Rose Chance; Shanghai; Mrs. Alden |
| Synopsis | Gudge is still missing and Shanghai finishes filling in the well. Shanghai ties up loose ends and silently leaves one night to go to sea. Before he leaves, he sends an anonymous letter to the police, telling them to "Look in the bottom of the old well." The police have their hands full trying to dig out the well and the public speculates on what happened to Gudge. |
| Script | Harold Gray |
| Pencils | Harold Gray |
| Inks | Harold Gray |
| Notes | Story continues on inside back cover in black, red, and white and concludes on the back cover in color. Last strip is dated November 20, 1938. |
| Reprinted | from Little Orphan Annie (News-Tribune Syndicate) newspaper strips from 1938 |