The wiring in the second photo is never going to work. Soldering to those vias is very precise, you need 30AWG wire or smaller (32 to 38AWG magnet wire is recommended), and liberal flux use for clean joints is a
must.
As for why it isn't working, USB data wires are very prone to interference. They must be as short as possible, twisted tightly together in a helix to ensure that they remain balanced, and all flux residue must be cleaned off to prevent transient shorts. 5v and GND must be supplied to the USB drive as well, else it will have no power to run on. You can't spaghet wire this like a low-speed logic breadboard project, unfortunately.
Also you have an errant solder blob that might be causing a straight-to-ground short