A lot got lost in translation here.
"Lot in life," means station or position a guy has achieved, so I think Hart was just delivering a old-Sportscenter-style riff on Dion is the sauce rn. Lewis telling him to stop sucking him maybe means he didn't like how overtly Hart was complimenting him, or maybe he didn't understand what Hart was saying and thought he was hating. I myself didn't take it as Hart saying Lewis is coddled in any way, just that he achieved such status that he was going to these places.
"lot in life" doesn't carry the connotation of "achievement". it implies that your position in life is determined by fate, i.e. not through anything you do. the origin comes from "drawing lots" to decide something--in other words, by chance.
hart, whether he meant to or not, was basically saying that lewis was lucky to be in the position he was in and that he was making the most of it. if he really wanted to highlight lewis' achievements, he should have said something like:
From Fenway Park to the ESPYs, Dion Lewis enjoying the fruits of his labor.
edit: by the way, i like your pun:
A lot got lost in translation here.
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