Important context: Voyager 1 is the fastest of them all, and New Horizons is the slowest, so they are never switching places—Voyager 1 will always be the furthest, then Voyager 2, then New Horizons.

There is a market that thinks that the chance of Voyager 2 outlasting Voyager 1 is 74%, which is almost equivalent to the 74% probability of Voyager 2 becoming the next most distant operational spacecraft. The possibility that there will be some other spacecraft that will overtake Voyager 2 by the time Voyager 1 breaks down seems very low to me.

[Edited: I wrote this comment before IHP-1 and IHP-2 were added, but they don't change much. "The goal of the spacecraft is to have travelled a total of 100 astronomical units by 2049" (Wikipedia), i.e. Voyager 1 will likely have been long gone when (if ever) they can compete with Voyager 2 and NH]