Sometimes bad trades can lead to bad trades. If we follow the ownership line from transaction to transaction, what “trade tree” would lead to the greatest number of bad deals? Going through every trade ever made in the NHL and connecting them together would require some painstaking research. I can't guarantee that this is the worst trade tree of all-time, but it's a contender and it all started with the Jaromir Jagr trade from Pittsburgh to Washington in 2001. That kicked off a series of unfortunate events that is still active today. Let’s follow the tree.
1) 2001, the Penguins traded Jaromir Jagr to Washington for a bag of pucks that included Kris Beech. None of the assets that the Penguins received in return for Jagr turned into quality NHL players. Jagr had led the NHL in scoring the year prior. I’m not sure there has ever been an Art Ross winner traded for less in the summer he won the award.
2) 2005, the Penguins eventually traded Beech to Nashville for a draft pick.
3) 2006, Nashville trades Beech and a 1st round pick (that became Semyon Varlamov) to Washington for Brendan Witt. Awful trade. Witt scored 3 PTS in 23 GP for the Predators who were eliminated in the first round of the playoffs in 5 games. He then left via free agency that summer. Varlamov is closing in on 400 NHL games. This made my list of worst deadline trades in the salary cap era.
4) 2011, Washington trades Varlamov to Colorado for a 1st round pick (that became Filip Forsberg), and a 2nd. Varlamov has been mostly mediocre since arriving in Colorado (aside from one great season), with the team only making the playoffs once in his 7 seasons. Forsberg on the other hand has become a star, scoring 229 PTS in 304 GP (and counting) in a Preds jersey. At this point in the tree, Washington has come out ahead, making three great trades, but it’s about to get worse.
5) 2012, Washington trades Cody Eakin and the 2nd round pick they got in the Varlamov trade for Mike Ribeiro. Washington was eliminated in the first round and Ribeiro bolted via free agency. Eakin has played over 400 NHL games since that trade.
6) 2013, Washington trades Forsberg to rent Martin Erat, which is among the worst deadline deals in NHL history. The Caps were eliminated in the first round of the playoffs (where they got zero PTS from Erat). This trade also made my list of worst deadline deals in the salary cap era.
I’m not sure if there has been a worse NHL trade tree in the 21st century. There are at least 5 bad apples on this tree. If we diverge from the direct ownership line to see what branches from other trees are attached to this one, it starts to get a bit wild. That 2nd round pick that the Colorado Avalanche traded for Varlamov has an interesting back-story. It had originally belonged to the Boston Bruins. The Bruins traded it to Toronto with a 1st round pick (that became Rickard Rakell) and Joe Colborne for Tomas Kaberle. It’s debateable if this was a bad trade, as Boston won the Stanley Cup, but he was only their 5th defenseman who contributed very little in the finals.
But wait, there’s more. Toronto turned around and traded that 2nd round pick to Colorado for JohnMike Liles. Liles was a bust in Toronto and was sent to the Marlies before being swapped for another bad contract in Tim Gleason (whom they later bought out). Certainly the two trades that attach the Kaberle tree to the Jagr tree are bad trades. This didn’t work out so great for the Leafs, who also traded the 1st round pick they got for Kaberle to move up in the order and draft Tyler Biggs. The Leafs got Biggs, the Ducks got Rakell and John Gibson in a classic example where trading 2 lower picks for a higher pick turned out to be an epic fail.
You might remember the name Tyler Biggs, but not for a glorious NHL career. He was traded with Phil Kessel to Pittsburgh. So now the whole Kessel trade tree is connected to the Jagr tree (although not by a route of direct chronological ownership). Guess who else is in that Kessel tree? Yes, one Tyler Seguin. Who was famously traded from Boston to Dallas in an awful trade that Bruins fans still complain about to this day.