Question

I had an argument with a friend regarding the Rebbe of Chabad’s words, and I’d be glad to hear your opinion.
Regarding the “trait of trust,” the Rebbe of Chabad wrote as follows:
“The obligation of trust that we were commanded in is not merely a detail and automatic result of the belief that everything is in the hands of Heaven and that the Holy One, blessed be He, is gracious and merciful, for there would be no need for a special obligation for that. Rather, this obligation is a service in its own right, whose essence and definition are that a person should rely and lean on the Holy One, blessed be He, until he casts his entire fate upon God, as it says, ‘Cast your burden upon the Lord,’ for he has no support in the world besides Him, may He be blessed.
And it may be said that this is the intent of what was written in Duties of the Heart, that trust is ‘like a bound servant who is in the prison house under his master’s authority,’ such that all the prisoner’s trust is only in his master, who ‘has delivered him into his hand, and no person can harm him or benefit him… except him.’
According to the Rebbe of Chabad’s words, the meaning of ‘trust’ is that the Creator will certainly do good for a person (and not as in the well-known view of the Chazon Ish). If so, the question is: who says so? From where comes the certainty that the Creator will do only good for a person? Perhaps he has sins, etc. etc.
The Rebbe goes on to explain:
‘This itself is the foundation of a person’s trust that the Holy One, blessed be He, will bestow good upon him in visible and revealed good, even if he is not worthy of this kindness:
The meaning of trust is not that he believes that since God’s kindnesses are without measure and limitation, both to the worthy and to the unworthy, therefore he will receive God’s kindness without any effort on his part (for if so, the whole idea of reward and punishment would be nullified) — rather, trust is labor and exertion of the soul, and it brings about God’s kindness, which comes as a result of the person’s labor and exertion in trusting in God. Through a person truly relying, in the depth of his soul, only on the Holy One, blessed be He, alone, to the point that he does not worry at all, this awakening itself causes the Holy One, blessed be He, to deal with him in this way, that He does good to him (even if otherwise he would not be worthy of it).’
That is the Rebbe’s view up to this point. One can disagree with the explanation itself for many reasons. I’m not getting into that; I’m only asking whether there is a logical problem in this proposal from the following angle:
In practice, if a person trusts that things will go well for him — what justifies that they really will? The very fact of the person’s exertion in internalizing that things will go well for him. Is that acceptable? Can a person be sure that there will be a table here, because he was told that if he is sure, there will indeed be a table here? a0
What do you think? Logically, is this a problem?