Benning's track record with blueliners is a bit concerning, although probably a bit overstated due to how unattractive a destination we have been the past few years. Other than RealGud though, Jimbo hasn't really made any significant investments that have been big misses at the position. It's been mostly short term, small dollar type signings, and a handful of mid round picks.
He did sign Stecher, so he has added a top 4 to the team. Plus some other decent UDFA signings that probably won't be core pieces, but reasonable organizational depth.
Hughes and Juolevi will go a long way in shaping Benning's Blueline legacy. If they both develop into top 4 players, along with Stecher, then in a couple seasons this conversation will be much different. Add in a Tryampkin return, and things would look good.
Don't see this being addressed at the trade deadline. Really not the time of year what we need will be available, short of am Edler trade which isn't happening. Defense will continue to be a work in progress for at least another couple seasons, but there is some solid long term pieces now in the organization.