I got my bike back. The city (DPW) messed up and it appears they mistook it for an abandoned bike. A reader mentioned in the comments section that a similar bike to mine that does indeed look abandoned was on the same block where mine was locked up. I also lucked out (sort of) in that I had a witness who saw the city take it. Otherwise I would’ve had nothing to go on and would’ve assumed it was a typical bike theft.
So, it doesn’t look like there’s anything as nefarious as a bike theft ring involving city workers, but it does seem clear DPW didn’t follow any sort of protocol to ensure they were removing the correct bike. I’m still out the price of a new U lock, but did at least get the satisfaction of having DPW drop the bike off to me in person, after insisting they do so.
As a postscript — at the urging of readers, I contacted some council members along the way. I learned that Evans’ office couldn’t care less about something like this, but Silverman’s office (Ashley Fox, specifically) was genuinely concerned and did what they could to help. Take from that what you will.”