In the parlance of the confidence game, a lookout is an operator who works outside the big game in order to keep track of the players and the mark.
For a short con, one lookout is usually sufficient. In general, this is the man "against the wall", also known as a slider or sider. He may very literally lean against a wall, putting him in a position well back from the action with no blind spots. In the case of short cons like the monte or one of its variants, his purpose is primarily to watch for the police and to signal if they should come along. This leaves the other operators free to run the game.
For most long cons, one lookout is often committed to the mark and doesn't leave his side (his shadow). Similar to a police stake-out, one or more lookout may watch the mark in shifts. When possible, the move is communicated to the operators so that they are aptly prepared and can make changes in the plan if necessary.
In addition to this, sometimes it is necessary to borrow a large amount of genuine currency to run a long con (later to be exchanged for counterfeit or decoy money once it has been examined and is considered genuine). In order to ensure that none of the operators nor the mark nor an ancilliary person makes off with the caboodle, it is considered wise (and fair) to put a lookout on the money. Certainly it is often a sizable and possibly dangerous investment which could possibly be on loan from the heavy guys.
If the long con involves a store, certainly another lookout (a lugger) might also be stationed nearby where he can keep a bird's eye view of the entrance. This way, he can signal the operators as to who is coming, especially giving them time to prepare themselves when the mark is on his way.
Many underestimate the skill required to be a lookout, and is therefore often considered to be simply muscle because he may need to exert force, but the lookout must usually be more than a thug. It is essential that the lookout not play a role (such as a stooge or a shill) in the big game— he should remain anonymous to the mark so that he is inconspicuous. At the same time, a lookout needs to understand the game intimately in order to know who to watch and why. For this reason, he cannot be muscle alone.
Indeed, for certain games, the lookout runs the show. Just like a stage play or motion picture has its director who remains neatly out of the scene, so sometimes it is necessary to keep the hub of the big game outside altogether. This allows coordination which would not otherwise be possible, especially in the modern age of cellular communications. By remaining mobile (often a shadow for the mark), he can receive reports from operators and messengers and coordinate the next step while shills are busy working the mark.
- INTELLIGENCE ANALYSIS OF WHITE COLLAR CRIME
- Scoundrel's Glossary