Now that’s a load.
Is a CDL required for where you are?
CDL is a federal requirement for combinations over 26,000lbs GVW regardless of what the state does, so in this case, yes. The truck pictured is 14,000GVW and the trailer is 16,000GVW = 30,000 GCWR, which requires a Class A CDL.
Believe it or not, if you towed this same load with a diesel 3/4 ton, no CDL is required. The 3/4 ton trucks are all rated at 10,000GVW and so combined they fall just shy of the requirement. However, a 3/4 ton doesn't really have enough payload capacity to handle this trailer with the tongue load pictured, especially if its a diesel 3/4 ton (which is pretty much needed for pulling this much weight). Maybe Ford's new 7.3L big block gas V8 would be adequate, I don't know.