Leo was lucky that Iesha made Lucky work really hard to get a set of handcuffs on her taking full advantage of the fact that she and Sissa had a natural advantage over those who had legs in certain situations like slipping under things or going through a narrow passage.
While he did catch her in the end, Lucky Lightfoot only did so with twenty seconds left before the maximum time limit was reached. He was rewarded with a little token that had a Leptus' cotton fluff engraved on one side and a snake coiled around a boat on the other with text hinting at its usage inscribed along the ridge of the coin like token.