Five Trade Deadline deals in the cap era that didn’t age well for the buyer

With less than a month until the 2024 NHL Trade Deadline March 8, we’re delivering at least one deadline-focused story every day at Daily Faceoff.

Today, we explore some recent deadline deals that didn’t pan out as planned for the buyer teams.

2024 NHL Trade Deadline Countdown: 19 days

The risk that always comes with being a buyer at the trade deadline is that if you’re bringing in a rental asset, you might be giving up a lot for someone who only plays a couple months and one round of the playoffs for your team. If you keep them around long term or you win the Cup with them, it’s worth it, but sometimes you pay a high price just to see them leave as quickly as they arrived.

I’ll be looking at some examples of deals at the trade deadline that did not age well for the buying team. It was trickier than I expected, usually because most deals either didn’t fetch a massive return, the prospects and picks didn’t amount to much, or trades that felt like an overpayment were for players that teams got term or championships with. But, there was still a good amount of options to choose from, so here are the five deals that stood out to me.

San Jose acquires Craig Rivet and 2008 5th round pick (Julien Demers) from Montreal for Josh Gorges and 2007 1st round pick (Max Pacioretty) – February 25, 2007

It was quite the arms race in the Western Conference in the 2006-07. By the end of the season, seven teams finished with at least 104 points, highlighted by the consistently elite Detroit Red Wings and the tough Anaheim Ducks. The Sharks were only a bit more than a year into the Joe Thornton era and wanted to add at the deadline to improve the team against a challenging West. Their choices: Bill Guerin and Craig Rivet.

Both players had solid stints with the Sharks and produced somewhat well in the regular season, but it certainly didn’t translate to the playoff success they hoped for. They only lasted two rounds in 2007 before Guerin moved on to the New York Islanders, while they met the same fate in the Sharks second attempt with Rivet in 2008 before he left for the Buffalo Sabres. This pick has less to do with the quality of the players, but more because the Sharks didn’t get too much out of Rivet’s time there, while the Canadiens got a lot out of their return. Josh Gorges would be a solid defensive defenseman for eight seasons with Montreal, and Max Pacioretty would score 30 goals five times in 10 seasons with the Habs and become their captain in the late stages of his time there. I’m sure both players would’ve fit in quite well on the Sharks instead of Guerin and Rivet, especially since they filled similar roles.

Detroit acquires Kyle Quincey from Tampa Bay for Sebastien Piche and a 2012 1st round pick (Andrei Vasilevskiy) – February 21, 2012

There are a lot of trades that could sum up the late stages of the Detroit Red Wings’ playoff streak where it was quite evident that the team was more focused on keeping their floor high instead of their ceiling to keep it alive. One of the best examples is the Kyle Quincey trade. First off, Quincey was a former Wings draft pick, so it seemed fitting for them to turn to their old reliable veterans. Then there’s the fact that he is a very safe defensive defenseman, helping keep that floor high.

And then there’s the return. Sebastien Piche isn’t really something they should have been worried about, but it’s the first-round pick that would come back to haunt them. A first round pick for Kyle Quincey felt like a bit too much in the first place, but the fact that the pick would go on to become Andrei Vasilevskiy doesn’t help them at all. In fairness to Detroit, that draft didn’t exactly have a large pool of elite talent, and there’s no guaranteeing they would have selected Vasilevskiy themselves, but you look at the state of their goaltending since, and you have to think they would like to have someone like Vasilevskiy in the crease for them. Ironically enough, it was current Wings GM Steve Yzerman who drafted Vasilevskiy when he was GM of the Lightning.

Ottawa acquires Cory Conacher and a 2013 4th round pick (Tobias Lindberg) from Tampa Bay for Ben Bishop – April 3, 2013

Okay yes, I’m recycling one of my trades from my best trades series, but can you blame me? This is a textbook example of buying high on an asset and seeing the other team reap the rewards. The Senators were ravaged with injuries in 2012-13, and needed a scoring touch to help them out, and Cory Conacher seemed like a great option with 24 points in 35 games in Tampa. At 23, he also fit in with some of the more youthful pieces on the team like Kyle Turris, Mika Zibanejad and Erik Karlsson, and with Craig Anderson looking solid and the hope that Robin Lehner would develop into the future starter, they didn’t need Ben Bishop.

While the Sens goaltending hasn’t exactly needed Bishop since then, Conacher ended up with just 25 points total in 72 games in Ottawa before they lost him for nothing on waivers. Meanwhile, Bishop solidified the crease in Tampa’s earlier competitive years before Vasilevskiy took over, and then Bishop went on to be a great goalie for Dallas before injuries ended his career. Even if the Sens didn’t need Bishop, they could have at least used him better as trade bait and gotten a superior player.

Washington acquires Martin Erat and Michael Latta for Filip Forsberg – April 3, 2013

This is another recycle from my best trades series, although this one was just an honorable mention, so I don’t feel quite as lazy picking this one. But this was one of those trades that you always remember happening because you remember the reaction was unanimously “what is Washington doing?” Martin Erat was a solid player for the Predators, coming off eight straight seasons in the range of 50 points, but Filip Forsberg felt like a lofty return, especially since he was looking like one of the best picks outside of the top 10 from the 2012 draft.

Lo and behold, this aged as well as everyone expected. Erat lasted just 62 games for Washington before they traded him to the Arizona Coyotes for an underwhelming return, and he only got 27 points in that span. Meanwhile, Forsberg has gone on to get the most points out of any player in that 2012 draft, and is the franchise leader in points per game among players with at least 500 games. The Caps at least got the Cup without Erat, but could they have won more with Forsberg in tow?

Ok, bear with me on this last one…

Pittsburgh acquires Derick Brassard, Tobias Lindberg, Vincent Dunn, and a 2018 3rd round pick (Justus Annunen) in exchange for Ottawa acquiring Ian Cole, Filip Gustavsson, a 2018 1st round pick (K’Andre Miller), and a 2019 3rd round pick (Anttoni Honka) & Vegas acquiring Ryan Reaves and a 2018 4th round pick (Stanislav Demin) for retaining 40% of Brassard’s cap hit – February 23, 2018

Yeah, there’s a lot going on here. Honestly, it was so many pieces, I almost ignored it. But then I noticed something. The only big player really moving in this deal was Derick Brassard. Ian Cole is solid as well, but this was very much the Sens selling Brassard, and the Penguins looking for a third-line center to fill their Nick Bonino-sized void there.

It seemed like a decent fit at the time considering Brassard had been a productive center for several seasons, but unfortunately, it just didn’t work out. He got just 23 points in 54 regular season games and another four in 12 playoff games before the Pens eventually moved on from him. On the other hand, a first round pick and a top goalie prospect in Filip Gustavsson already felt like a bit of a steep price, and it didn’t age any better with Gustavsson turning into a good goalie in Minnesota, and that pick going on to become K’Andre Miller (although in typical Sens fashion, neither came to their benefit). I want to cut the Pens some slack since they had just won back-to-back Cups, but this still felt like a risky trade, and was the beginning of their current stretch of mediocrity. Also, just to clarify, that is a different Vincent Dunn, so no, that doesn’t save the Penguins in this trade either.