It may be worth noting that a few years into Drew's time as host, offering (and awarding) more expensive showcases on a more regular basis was prioritized, which, to my casual observation, came at the expense of getting wins in the first five-sixths of the show.
I don't remember when it seemed like that practice was at its peak, and tpirstats.com didn't keep track of showcase prices back then. However, looking at tpirstats.com's pricing game win–loss records for each season may offer a hint:
(Season 36 was Drew's first season; all numbers are presented as win–loss)
Season 36: 535–605
Season 37: 460–686
Season 38: 415–725
Season 39: 398–742
Season 40: 450–696
Season 41: 485–649
For comparison, season 52's record was 509–631, and season 53 (the most recent complete season)'s record was 520–620.