First, a few bad signings. Back in the day, signing any free agent meant you had to give up compensation (Thanks Alan Eagleson!). A signing was basically a forced trade.
July 25, 1991: St. Louis signs Brendan Shanahan.
Sure Shanny is in the HHOF. But the signing cost the Blues Scott Stevens, who is also in the HHOF.
March 5, 1994: St. Louis signs C Petr Nedved from Vancouver
Because of this signing, there was an arbitration case in which the Canucks asked for Brendan Shanahan and the Blues offered Craig Janney. The arbitrator awarded Janney, but Janney refused to report to Vancouver. The Blues got Janney back for Jeff Brown, Bret Hedican and Nathan Lafayette. Then the Blues lost Nedved four months later when the NHL sent him to the Rangers as compensation for hiring Mike Keenan.
July 28, 1995: St. Louis signs Shane Corson.
The Blues wanted to sign two RFA's: Shane Corson and Martin Brodeur. They screwed up and did things in the wrong order. As compensation for signing Corson, the Blues sent 2 first round picks to the Oilers. They got the picks back by trading Curtis Joseph and Mike Grier. When they tried to use the picks to compensate the Devils for RFA Martin Brodeur, it got shot down by NJD President (sorry NHL President) John Zeigler. In the long run, Grier for Corson straight up would have been a poor trade.
And now the trades
Februrary 1, 1986: Blues send Terry Johnson, Joe Mullen, and Rik Wilson to Calgary for Eddy Beers, Charles Bourgeois, and Gino Cavallini.
Mullen had held out briefly before the season started. Cash-strapped Harry Ornest, fearing he couldn't afford to keep Mullen, pushed Ron Caron to deal Mullen. Eddy Beers had scored 39 and 40 goals the two prior seasons but had his career cut short by a back injury. Joe Mullen went on to the HHOF.
September 6, 1988: St. Louis trades Doug Gilmour, Mark Hunter, Steve Bozek, and Michael Dark to Calgary for Mike Bullard, Craig Coxe, and Tim Cokery
Gilmour was traded after he was sued for allegedly having a sexual relationship with a 14-year-old girl. Bullard was coming off a season of 48 goals, and had scored 51 in 1983-84. 2 months later Bullard was traded to Philadelphia for Peter Zezel. Doug Gilmour is in the HHOF.
March 5, 1991: St. Louis trades Cliff Ronning, Geoff Courtnall, Robert Dirk, Sergio Momesso, and a 5th-round pick to Vancouver for Dan Quinn and Garth Butcher
An early deadline stinker that left the Blues with no scoring depth. It also paved the way for Vancouver's first cup run. This also led to:
September 22, 1991: Blues trade Rod Brind'Amour and Dan Quinn for Murray Baron and Ron Sutter.
There was some weirdness about this deal at the time but I don't remember the details. I think maybe Quinn was “bad in the room”. I do remember that Dan Quinn was accused of rape, but that was in 1992 (the charges were later dropped). Brind'Amour had been offered to the Devils as part of the Brendan Shanahan compensation package. Brind'Amour of course went on to win the Cup in Carolina.
February 7, 1992: Blues deal Adam Oates to Boston for Craig Janney and Stephane Quintal.
Oates came to town in one of the Blues best trades (Oates and Paul MacLean for Bernie Federko and Tony McKegney). He had renegotiated his contract in 1991. 6 months later he demanded another renegotiation but was sent packing. Oates went on to the HHOF.
March 20, 1996: Blues trade Jean-Luc Grand-Pierre, 1996 2nd round pick (#27-Cory Sarich), and 1997 3rd round pick (#69-Maxim Afinogenov) to Buffalo for Yuri Khmylev and 1996 8th round pick (#196-Andrei Podkonicky)
Ah, the Mike Keenan era. So much drama. Khmylev played 9 games for the Blues before being released.
December 5, 2001: Blues trade Sean Hill to Carolina for Steve Halko and 2002 4th round pick (#124-Lane Manson)
I thought Hill was a great signing by the Blues but he never fit into Quenneville's system. Halko held (Holds?) the record for most NHL games played without scoring a goal (155).
August 2, 2005: Blues trade Chris Pronger to Edmonton for Eric Brewer, Doug Lynch, and Jeff Woywitka
The Blues failed to manage their payroll going into the 2004 Lockout. Hopelessly over the Salary Cap they faced a tough decision. Rather than buy-out Doug Weight or Keith Tkachuk they traded Pronger. Later that season they sent Weight and Erkki Rajamaki for Jesse Boulerice, Mike Zigomanis, Magnus Kahnberg, Carolina's 1st round draft choice, Toronto's 4th round choice, and Chicago's 4th round choice.
July 23, 2007: Blues trade Carl Soderberg to Boston for Hannu Toivonen.
Soderberg is Boston's 3C. Toivonen played 23 games for the Blues with an overall save percentage of 0.878.
February 26, 2008: Blues deal Bryce Salvador to Devils for Cam Janssen.
Salvador has continued to be a steady defensive defenseman. Janssen has continued to be Cam Janssen.
February 28, 2014: Blues trade Jaroslav Halak, Chris Stewart, William Carrier, 2015 1st round pick, and a conditional (possibly 1st round) pick to Buffalo for Ryan Miller and Steve Ott.
This was supposed to be like spinach for Popeye. It worked out more like kryptonite for Superman.
Miller and Ott. Either half of this deal would be a candidate by itself. Ott and a prospect for Stewart would have been a reasonable (if quixotic) deal. Halak for Miller was a lateral move at best. Miller wasn't as good in the regular season as Halak was and the playoff results speak for themselves. Throw in first and third round picks. Awful.
Some of the awfulness is the opportunity costs. We didn't get Vanek, Moulson, etc. who would have made the offense better. I'm sure the older trades had opportunity costs too, but thankfully I don't remember them.