As was mentioned, If water was coming out where you mentioned the seal is probably worn out and needs replaced.

Here is a general breakdown of a pump similar to yours,
http://www.piecesml.com/english/en-proc..._icon.html

Pumps like that are generally made to be repaired if nothing catastrophic goes wrong.

Get a rebuild kit and replace the seals, bearings, vanes and it will be like new.

The leak may have went away temporarily but when you start calling for brew pressure I would not have a lot of confidence in it

Most machines of this caliber have a two position power switch such that position 1 allows the machine to fully function w/o any power to the heating element(s). Position 2 allows for power to the heating element(s). Leave the switch in position 1 only for the time being.

Do you have a maintenance manual/installation manual/operators manual for this machine? If not, obtain same ASAP from the nearest La Cimbali dealer if possible.

A light on the machine indicates the boiler is filling, but it is not.

That light probably comes on when the boiler fill solenoid valve receives power. If, in fact, the boiler is not filling, that's all the more reason to not send power to the heating element and uncover why the boiler is failing to fill.

The "bellows like" connection between the motor and pump SHOULD have a small hole (~ 1/16") in the bottom. This is called a weep hole and any leakage there is not good but better there than to find its way into the motor/motor bearings and wreck them as Chris has suggested. All of the rotary pumps in our espresso machines are equipped with precision mechanical seals, possibly user replaceable, but more than likely not. I suggest you first uncover the reason for the boiler not filling as the potential cost and technical knowledge/time involved there glows in comparison to simply expending ~$35 to obtain a rebuilt exchange pump.