Trump's decision to commute Roger Stone's sentence has stuck many as unnecessarily risky in the run up to the election. It appears to send a message of cronyism, of looking after one’s own even if they are guilty (and this is not a pardon so Trump seems to either acknowledge Stone's guilt or considered a pardon a bridge too far). And while his "deplorables" won't care, it will give many of his less committed supporter pause. So why, when most around him were advising against, did he make such a bone-headed decision? In fact it may be quite rational, calculating even, and signals two inter-related things.
First that he realizes his chances of being elected are now slim and since he's already lost many of the "non-deplorables" who helped put him in office, his commuting of Stone's sentence won't really matter much. He has said "I could stand in the middle of 5th Avenue and shoot somebody and I wouldn't lose voters," so he likely believes that for his die hard supported this matters not an iota.
And second, if he's not re-elected there are plenty of shady dealings from his past that the Southern District of New York has been looking into since he came to prominence that, if things go badly, could have serious consequence for him. Since he can't run out the clock on the statute of limitations by exerting executive privilege and presidential immunity if he's turfed out of the White House, Roger Stone, had he been he locked up, might have been "persuaded" to dish dirt on Trump in exchange for a shortening of his sentence. By commuting his sentence the risk that Stone rolls on him goes away.
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