If it's 5-0 and you let that in with 2min to go in the 3rd to make it 5-1, no big.
Up 2-1 in a hard-fought game mid-way through, and you let that in to tie it 2-2; that's a much bigger deal.
I think that's purely speculative and purely hindsight now that the consequences are well understood. Above all else, that wasn't the directive at the time. Imagine it's 2019, and the team is in a playoff spot, but JR says, "Ummm...nope, not going to focus on improving the roster, the playoffs or Cup. I'm going to retool instead so that we MIGHT be a playoff team in 2025." He would have been roasted by every hockey person in the world and promptly fired.
These are only tweets you can make with hindsight.