I guess I'd go with just about any offseason trade that has happened since Lidstrom retired as examples of deals he could have attempted to make, but didn't. Just about any Blackhawks trade in recent years -- Saad would be awesome to have these last two years, as would Nick Leddy. Boston has made some extremely regrettable trades involving very high quality players in recent years with Seguin, Lucic, Hamilton, and Boychuk. Any of those guys played very large roles for their teams and would have been really smart pickups for what they ultimately returned. The Blue Jackets acquired Foligno coming off a 47 point season for Marc Methot. Foligno is really up and down, but he can absolutely make a huge difference when he's playing well. I understand that recent trades such as Weber for Subban and Larsson for Hall are unrealistic, but there have been opportunities to improve the team via trade, and Detroit clearly hasn't made it happen. Winnipeg had a situation all offseason with Trouba, but nothing happened. Now he's playing 23 minutes per night out there.
I don't think it is a fair argument to say that there aren't high quality players available, or that Detroit doesn't have the pieces to bring them in, because every year it seems like there is some sort of trade that makes no sense. You just have to be able to make it happen. Kyle Turris returned a 2nd rounder and a high end prospect a couple years ago. He was a 3rd overall pick. He had yet to develop into a higher end player, but it was clear that he had the talent level to become something good. Filip Forsberg returned Martin Erat. Ryan Strome is a recent name that has come up as a potential trade candidate. Expect Holland to have any interest in that? Probably not, but the kid scored 50 points at the age of 21. He's a former 5th overall pick. Elite talent level? Possibly.
The point is, there's always some team that is ready to let go of a solid player, and you just have to work the phones and try to work something out. Holland hasn't made a legitimate trade in years. You cannot tell me that he hasn't fielded a phone call that could have landed him a player with unreal talent in half a decade or longer...