Reaching out to an MD on the other side of a deal - good idea?

Context:

  1. This deal is long closed (more than 1yr)
  2. The other investment bank is much larger than the one I interned at (think tier 10 city boutique IB vs NY EB)
  3. I only worked on this deal for ~1mo as my internship started midway through the process

I go to an extreme non-target, networking in NYC is tough as only two (2) alumni are working there. Would reaching out for a virtual coffee chat to hear about the other side of the deal be a good idea to hopefully try to weasel my way into something?

What would I need to have locked down before going into it?

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