That is exactly how the Silk Road guy was finally identified and caught.
It seemed like parallel construction [1] to me. Considering that the NSA is known to give the DEA "tips" [2], and has a division specifically to start parallel construction investigations [3], and this was a high profile drug case, it would be odd that they didn't use parallel construction techniques.
[1] https://en.wikipedia.org/wiki/Parallel_construction
[2] https://arstechnica.com/tech-policy/2013/08/us-drug-agency-g...
[3] https://www.reuters.com/article/world/exclusive-u-s-directs-...
The IRS guy figured it out and nobody would act on it because they all figured the FBI would know better and they should wait for the FBI to do it right. ... but actually he nailed it.