The bicycle brake and shift operation device is a device mounted on a drop handle of a bicycle, and includes: a bracket, a lever member, a winding body, a positioning mechanism, and a shift position display portion. The bracket is mounted on the drop handle. The lever member is a member that is pivotally supported by the bracket. The winding body is mounted to be rotationally movable on a support shaft provided on the lever member, and engages with a shift cable. The positioning mechanism, supported by the lever member, is a mechanism for positioning the winding body to positions that correspond to a plurality of shift positions of a rear derailleur. The shift position display portion is mechanically interlocked with the rotational movement of the winding body to display shift positions.