Good lord willing and the creeks don’t rise.

It will definitely happen, the only real question is if we're still talking to New Horizon when it passes Voyager 1.

In fact I wonder if we'll stop talking to Voyager 1 before or after New Horizon.

New Horizons is slower than Voyager 1, and is also decelerating more. New Horizons will never pass the others. Voyager 1 is the fastest probe in an escape trajectory.

https://en.wikipedia.org/wiki/Voyager_1#Far_future

For some reason I thought I had read that Horizons was faster and would eventually eclipse it, odd.

Anyway I'm still curious if V1 outlasts New Horizons

I am sure that your article said that it's newer and the launch event was on the plane of the ecliptic.

I read that one too.

Anyway, the Wikipedia article says:

  After 2036, both [Voyager] probes will be out of range of the Deep Space Network.[14]

As for New Horizons:

  [The RTG] will decay too far to power the transmitters in the 2030s.

So we could lose contact with three in succession. Or, the DSN could become even deeper!