That is working.
Not if you lose your bet that anyone is willing to pay you your desired wage. Then it’s unemployment because you gambled and lost. And even if they do agree, it’s just luck that you won— but it’s still a gamble.
Unemployment insurance is insurance too so I wouldn’t apply for that as a matter of principle.
Good thing it’s typically mandated by state law. You don’t have a choice when it’s deducted from your paycheck in most cases, and you’re automatically enrolled. (In some states and situations, it’s paid for by the employers). Whether you ever take advantage of that is another matter.
However, that’s irrelevant. All you’ve done here is demonstrate poor decision-making skills, and a profound misunderstanding of the concepts of both insurance and gambling.