When is the last time these top teams made a trade in season to weaken their roster for a prospect? The answer is never. The Blues are rebuilding so I'm sure they made plenty of those moves in the last few years.
I don't disagree that this team has been very trade shy since Treliving has taken over, but that doesn't mean they should do questionable roster decisions either.
Trading Woll to fill a future need isnt a questionable decision imo. It is building for next year and onwards while giving the reigns to Stolarz who has a cheap deal and can play 50-55 starts. Also get a backup in goergiev you bank on to rebound under the leafs defensivw system.
Getting a 2C is almost impossible for us unless we draft at this point. We can sign and draft 1B goalie (have a few in the system, and goalies are often available if you are willing to take a bet and have good internal goaltending coaches and scouts)
While I can't think of an exact trade like Woll + Robertson for Ritchie + Goergiev a few Trades where teams dealt a good player for future oriented results would be:
Blues: 2016-2017 TDL --> sell Kevin Shattinkirk as a pending rental who many fans wanted to extend as Blues were in a playoff spot and had made WCF in 2016. They got sanford who played 8 games in 2019 cup and had 4 pts and bigger piece in a 1st which they used at the 2017 draft to acquire Brayden Schenn an elite 2C foe them for half a decade
Panthers: 2022 summer --> Huberdeau off a hart levek year + Weegar (#2/3D) +1st for Matt Tkachuk. Changed the strategy and playstyle within the org, with the trade initially being considered a longer term move with Panthers sacrificing win now assets to get Tkachuk who could fit in better long term for the Panthers to contend. Got 2 finals and a cup out of it so far and remain a top 2/3 contender for this season
VGK: Dumped Fleury in 2021 summer, bwing aggresive and flexible on who their starting goalie will be to get them a cup
WSH --> 2011 summer. Traded Varlamov to the Avs for an unprotected 1st rounder. Caps lost in R1 in 2011 playoffs and Varlamov was one of their 2 very good goalies. They used the position of strength and sold him going with Holtby. They did butcher the deal trading 12th OA in 2012 (Filip Forsberg) for Erat, but this was a similar type move to dealing Woll for Ritchie