The fact that we had no leverage in the deal might also shoot holes in the whole "we should have asked for Reggie Jackson" speculation.
Eh, they had no leverage, but neither did the Thunder with Reggie Jackson. It's not like they got back a ton for him either. I suspect OKC would have done a straight Jackson for Kanter swap. I do know the Jazz were never particularly interested in Jackson, as they felt Jackson's lack of shooting wouldn't work long-term next to Favors and Gobert. They knew Jackson would want big money too (5 years, $80M)
That's turned out to be a little bit of a mistake because Jackson figured out how to shoot. Back then, he was shooting 27% from 3 and shot 21% and 23% in two seasons before that. They weren't confident that he'd be worth whatever he'd get in FA. The other weird thing about Jackson is that his defensive numbers was and are kind of disappointing, both in OKC and now in DET. He's not a big liability, but less of an impact player than you'd hope for. And of course, there's the Exum thing. Jackson was awful in OKC's locker room, and what if Exum got good and deserved to play over him? It might have gotten ugly.
But let's say they made the trade. They're almost certainly in the playoffs last year, so that's good. They don't have to trade a 1st for Hill (who I think is in the same tier, probably, and IMO Hill's a better fit. But I also suspect IND does a Jackson/Hill swap. We're now on hypotheticals of hypotheticals.), but don't get one back from OKC in the trade. And you have whatever Jackson is worth in this market, which is probably something positive, even at $16M annually.
Anyway, not grabbing Jackson was probably a mistake in hindsight. But I get why DL made the decision he did, and I probably would have done the same then too.