blackdoghatesskunks was wondering about concrete examples of the dickery of slippery Rich Winter (y, just to make the trifecta). I had been going to respond in a comment there, or else on mudcrutch79's post on a similar subject, but this got really long - mostly because there's so much dickery to be seen. So, in reverse chronological order:

All Oilers fans should know about what happened with Mike Comrie in 2003. For non-Oilers fans, here's the gist of it: Comrie was a restricted free agent, but he wouldn't sign a contract with Edmonton. He said at the time it wasn't about the money. My opinion, but not mine alone, was that he felt mistreated by Oilers management, particularly some comments coach Craig MacTavish made along the lines of he (MC) wasn't as good as he thought he was, and was considered a second-line centre. Of course, that's partially my opinion because I figured the same: a very good second liner, but a second-liner nonetheless, somebody who could rack up lots of points against weaker opposition, but nobody you wanted out against the Peter Forsbergs and Joe Thorntons. But I digress. Rich Winter said that the whole story would come out after the trade. After the trade, he backpedaled somewhat. We're still waiting.
Holdout Vaclav Varada, 2002 with the Sabres. "It was frustrating because they were throwing nickels around like they were manhole covers . . . They're just not in a position to split the difference. The Rangers can split the difference, but they just can't."[1] Varada missed training camp that year, was a RFA, had 23 points in 82 games the year before, and was -7, but he turned down a 1.1m qualifying offer, which was below average salary at the time.
"Frog Gate" - 2000. Ottawa Senator Vaclav Prospal (allegedly?) called Montreal defenceman Patrice Brisebois a frog. Winter called Brisebois "gutless and spineless" and referred to him as "hiding behind his skirt," and said "he should have stood up like a real man and settled this on the ice or on the back lot."[2] I don't think I need to tell anybody what Francophones usually think about being compared to certain small animals of the amphibious nature. Of course, Edmonton's own Georges Laraque wasn't very complimentary of Brisebois at the time either, but at least he didn't claim that Brisebois was somehow less of a man.
September 1999: Petr Sykora, a New Jersey Devil, didn't report to training camp despite a valid contract; he wanted a raise. The Devils suspended him.
Somehow, though, Winter came out all compliments for Edmonton in 1999: he was quoted by Scott Zerr of Sun Media (in the Toronto Sun) as saying that small market teams had to be "smarter and more efficient." He went on to say that some of the fringe benefits in Edmonton (and other markets) outweighed pure salary, and mentioned Bill Guerin and Tommy Salo by name as being "excited to be in Edmonton" and that Petr Sykora loved the system there. A few months later - see above - Sykora was holding out from the Devils. So much for benefits outweighing salary.
1997: Rangers LW Esa Tikkanen was a free agent. Winter, representing him, was quoted as saying that they'd been talking to the Panthers, but "[w]e're not pulling Bryan [Murray, GM of the Panthers]'s chain. . . . We're not doing this to bump up the Rangers' offer."[4]
1996: Frank Musil, a defenceman with the Ottawa Senators, was a Rich Winter client. Winter, negotiating a deal with Ottawa GM Pierre Gauthier, complained that he'd been thrown out of Gauthier's office. 24 hours later, Musil signed a contract with Ottawa.[5]
1995: Winter accused Mike Keenan of making no sense. I guess he'd know. "He's the same guy who paid 1.5 million more for Dale Hawerchuk than he had to, traded a 50-goal scorer (Brendan Shanahan) for an unproven player (Chris Pronger), traded Esa Tikkanen for a draft pick. The only thing you can say about Mike is that he's consistent. But no one in hockey is saying he's consistently smart."[6] Well, Shanny's a great player, but I think Keenan got the best of that trade anyway, and what kind of agent complains about a player getting paid too much? I'm guessing Hawerchuk wasn't a Winter client.
1995: Surprise surprise, another pair of European Winter RFA clients holding out, Peter Bondra and Michal Pivonka of the Washington Capitals, who finally signed late October, into the regular season. The Capitals scheme had Bondra taking deferred payments starting in 2005 and going til 2012. Winter said that that actually would cost Washington less money than a previous offer (despite the dollar value being higher). Both players signed IHL contracts with the Detroit Vipers in order to gain leverage. Hopefully Winter got them cheap insurance, in case they suffered career-ending injuries.[7] Simultaneously, Igor Ulanov, another unsigned RFA with a different agent, was playing exhibition games with the Capitals. Both Bondra and Pivonka at least attended training camp.
1994: Dominik Hasek left the training camp of the Buffalo Sabres in September, in order to avoid injury while he was waiting for a new contract.[8] The team suspended him. This was a year after he won the Vezina Trophy, and he had an option year left on his contract. Winter had said earlier that the Sabres "don't appear seriously interested".[9] Winter had been looking initially for a \$5 million a year contract (when Hasek had previously been earning \$600,000 and Patrick Roy had made \$4MM Canadian).
1993: Winter client Craig Muni was traded by the Edmonton Oilers to the Chicago Blackhawks. Muni threatened to not report, citing potential loss of income from off-ice interests. The Hawks said they would suspend him if he didn't report for a game. He did report after a few days, after finding somebody to help with the travel agency he'd started up; Muni was traded to the Buffalo Sabres the next season though. Muni didn't have much good to say about Edmonton's management after the season was over either.[10] That wasn't the end of the drama though: the player the Oilers traded Muni for, Mike Hudson, turned out to have nerve damage that the Oilers felt the Hawks hadn't told them about.[10a, because I didn't feel like renumbering everything after this]
Earlier that season, Winter claimed that the contract forward Vladimir Vujtek had signed with the Montreal Canadiens wasn't valid because it hadn't been translated into Czechoslovakian. Vujtek was an Oiler at the time.[11] The NHL rejected the claim.
1991: Czech David Volek asked for a trade from the New York Islanders. Winter said that the reason was because Isles GM Bill Torrey had promised to renegotiate his contract, but didn't. Volek was in the fourth year of a 5 year contract at the time. The Islanders were up for sale at the time; the article says "Winter said he hoped he pending sale of the Islanders was good for business if it frees up some of Torrey's time so Torrey can deal with other matters."[12]
Colby Cosh noted what happened with Fuhr in the comments on the original BofA post, so I won't go into them here.
September 1989: Ron Hextall, then a Philadelphia Flyer and a Winter client, declared his contract invalid just before the start of training camp (8 September). He was suspended from play by the NHL for a fight in the previous year's playoffs, but had been practising. Hextall said that negotiations had broken down after the Flyers demanded he fire Winter, and he refused. Bobby Clarke was Philadelphia's GM then (as he is now). Hextall did return to practising with the team in late October, however.[13]
June 1989: Esa Tikkanen had his contract with the Oilers voided by the NHL mediators, thanks to some work by Winter. There's not really enough information in the article[14] to say whether this was Wintery-dickery, but it's at least weaselly.
And finally, 1988: David Volak first was rumoured to be defecting from the Czechoslovakian national team while it was in West Germany.[15] I only put that in because of what happened later with the Islanders. And also so that I could remind the young'uns that might be reading this that yes, there really did used to be a West Germany, as well as an Eastern one, and it used to be that if people didn't like life in the Warsaw Pact countries, they had to sneak out under the cover of night.
That's as far back as the archives to which I have access go; 1999 was the start of the assault on Alan Eagleson, spearheaded by Rich Winter. I guess it takes nasty to know it.
[1] - Buffalo News, 8 October 2002.
[2] - Atlanta Journal Constitution, 9 January 2000.
[3] - Toronto Sun, 29 April 1999.
[4] - Miami Herald, 19 July 1997.
[5] - Washington Post, 19 March 1996.
[6] - Toronto Star, 5 November 1995.
[7] - Multiple Washington Post articles, September and October 1995.
[8] - Buffalo News, 21 September 1994.
[9] - Buffalo News, 10 August 1994.
[10] - Pittsburgh Post-Gazette, 26 March 1993; Chicago Sun-Times, 28 March 1993;Toronto Star, 2 April 1993.
[10a] - Chicago Sun-Times, 29 March 1993.
[11] - Toronto Star, 4 February 1993.
[12] - New York Times, 12 December 1991.
[13] - St. Louis Post-Dispatch, 20 October 1989.
[14] - Toronto Star, 29 June 1989.
[15] - New York Times, 26 July 1988.