I nominate any player moves undertaken by the St. Louis Blues in the 1990s — player moves which were the driving force behind the escalation of NHL player salaries during that era. In fact, if one really traced it back, the financial mess that necessitated the lockout could probably be followed back to the St. Louis Blues.
Their offer for Scott Stevens was tremendously controversial at the time. They put out a ton of money for Scott and forfeited a ton of draft picks as a consequence.
They gave Petr Nedved a ton of money as a RFA and forfeited Craig Janney (traded back for Jeff Brown, Brett Hedican and Nathan Lafayette after he refused to come to Vancouver) as compensation.
There are other examples of St. Louis largesse but those are the two most notable.
Then New Jersey signs Stevens and St. Louis gets Shanahan as compensation. What the heck was up with that dumb player compensation system?