This isn't entirely outlandish, it just depends on the horse. Some do just fine with the turn around, others don't get 4-6 weeks in between and they come apart. I say take each situation on a case by case basis. Sir Barton had 4 days between the Derby and the Preakness. Then he won the Withers, then he won the Belmont. 4 races, 32 days, and him with tender feet. The Preakness was 1 1/8 and the Belmont 1 3/8 but still, not easy.
If he runs hard and barely gets the Trial, they might decide to wait for the Preakness. Give Ramsey some credit, he's not gonna kill the horse just to make the field. Pleasant Prince isn't by Kitten's Joy (like Dean's Kitten) or Catienus and we all know how much he's supporting them. He could have the Derby experience with a son of his own stallion, but he's taking this a step further. He's not just entering to enter, he seems passionate that the horse could win. PP's not bred like a sprinter, and I haven't heard of his mental issues being on par with Eightyfiveinafifty. This could work out just fine, and if it doesn't, it's not that horses can't/shouldn't do it, full stop. It just depends.
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