The text of Catch a Ride states that you select 1 target to deal damage to, then Sky Scraper also deals that target damage. With something like Dual Crowbars, Catch a Ride probably only effects the first target, but since your target was destroyed... That's my two cents.
1. Skyscraper targets and causes fixer to hit devil 2. Dual crowbars takes effect thus allows fixer to hit deadline. 3. Since devil died in #1, there was no valid target left for catch a ride (specifically for "skyscraper deals 1 target dealt damage that way..." Part of the card text, which was the devil), thus it "missed."
I learned with the current weekly one-shot that catching a ride on Mr. Fixers Jack Handle let Skyscraper choose among all the targets.
Karl & alien shampoo are correct - the target "dealt damage that way" was New Jersey Devil, and since it was destroyed there is nothing for Sky-Scraper to do.
It seams the interpretation of the words on Jack Handle "whenever Mr. F would deal damage to a target, he deals that much target to all non hero targets" and " Whenever Mr. F deals damage, he may deal that damage to 1 other target as well" are different in regard of targets dealt damage that way. I don't understand the difference.
Jack Handle is changing the targeting of the same instance of damage, and Dual Crowbars is creating a second new instance of damage.
I just did the same thing, targetting the villain first, and still didn't get the extra damage.