Every NHL season, teams look for that perfect trade deadline move—one that gives them an edge for a deep playoff run. But not every big deal works out. In fact, some trades look downright painful in hindsight. Over the past 15 years, several teams have paid high prices for players who didn’t live up to expectations.
Let’s look at six trade deadline moves that ended in disappointment on the Regret-O-Meter.
1. Blues Regret Ryan Miller Deal (2013-14)
The St. Louis Blues made headlines when they brought in goalie Ryan Miller and Steve Ott from the Buffalo Sabres. In return, they gave up a first-round pick, a third-rounder, and key players like Jaroslav Halak and Chris Stewart.
Unfortunately, the deal backfired. Miller struggled in St. Louis and was average in the regular season. In the playoffs, he allowed 19 goals on 185 shots, and the Blues were knocked out in the first round.
2. Tanner Jeannot: Tampa Paid Too Much (2022-23)
The Tampa Bay Lightning gave up a huge package—including five draft picks and young defenseman Cal Foote—to get Tanner Jeannot from Nashville. Jeannot had a strong rookie season with 24 goals, and Tampa hoped he’d bring grit and scoring.
But in 75 games with the Lightning, he only scored 18 points. He added just one point in the playoffs as the team made two straight first-round exits. That’s not a good return for the price they paid.
3. Tatar Trade Let Vegas Down (2017-18)
Vegas sent three draft picks, including a first-rounder, to Detroit for forward Tomas Tatar. He played fairly well in the regular season but disappeared in the playoffs.
Tatar was scratched in 12 of 20 postseason games during the Golden Knights’ run to the Stanley Cup Final. If he had delivered more, maybe Vegas could’ve won it all that year.
4. Eric Staal Disappoints Rangers (2015-16)
The Rangers hoped Eric Staal would be a game-changer after trading two second-round picks and a prospect to Carolina. Sadly, it didn’t work out.
Staal scored just three goals and six points in 20 games. In the playoffs, he was held pointless as the Rangers were eliminated in five games. A big name, but not a big impact.
5. Columbus Strikes Out on Gaborik (2012-13)
The Blue Jackets went for a splashy move by getting Marian Gaborik from the Rangers. Gaborik played well, but Columbus still missed the playoffs. Injuries held him back the next season, and he was traded again in 2014.
Columbus gave up key players like Derick Brassard and John Moore for a player who couldn’t help them reach the postseason.
6. Chicago Trades Danault for Little Return (2016-17)
The Blackhawks sent Phillip Danault and a draft pick to Montreal for Dale Weise and Tomas Fleischmann. Weise barely played, scoring just once in 19 games.
Meanwhile, Danault became a top two-way center in the NHL. This deal stings even more as Danault grew into the kind of player Chicago could’ve used for years.
Not every trade deadline move is a winner. These six deals show that big risks don’t always pay off. Whether it was giving up too many picks or trading away future stars, these teams were left wishing they could turn back the clock. Sometimes the best trade is the one you don’t make.
