I think it could hurt him if they play up the wealth angle.
After all, at least some of Trump's rhetoric is based on the "I'm an outsider against the elites" concept. Seeing a bunch of rich people released from jail might dig into that.
By the way, this poll was taken early last year (before Pardon-Pallooza) but it shows many people (including many republicans) would object to him pardoning people associated with him.
https://thehill.com/hilltv/what-ame...nt-of-americans-oppose-trump-pardoning-former
Seventy-six percent of voters contacted for the March 16-17 survey said they opposed Trump extending executive pardons to his former political aides. Only 24 percent said they would approve of the pardons....Seventy-six percent of voters contacted for the March 16-17 survey said they opposed Trump extending executive pardons to his former political aides. Only 24 percent said they would approve of the pardons.
What skills did he learn from Reality TV?
Trump was not the creator of the show, and credit to making him "look good" belongs to the staff of the show. His 2016 campaign was largely a dumpster fire (with Trump making multiple gaffs), and he only succeeded through a combination of 1) Russian interference, 2) A favorable electoral college, and 3) an opponent who had been smeared almost continuously by republicans for years.