The problem with checked exceptions is they are best explained and utilized in a single threaded execution model where the exceptions can be bubbled up to the operator.

This is not, of course, the only way that checked exceptions can be utilized. But, all too often, that is by far the easiest way to reason on them. They represent a decision that needs to be bubbled up to the operator of the overall system.

Worse, the easy way to explain how the system should resume, is to go back to where the exception happened and to restart with some change in place. Disk was full, continue, but write to a new location. That is, having the entire stack unrolled means you wind up wanting the entire process reentrant. But that is an actively hostile way to work for most workflows. Imagine if, on finding a road was closed, a cab driver took you back to pick up location to ask what you want to do about it.

If it is not something that you want to unwind the stack, or bubble up to the users, then you go through effort to wrap it so that it is another value that is being processed.