Sometimes it's better to hold onto certain draft picks since they could turn into great players as the Blackhawks have found out over the years.
Every team in the NHL has made mistakes by trading away draft picks that turned out to be good NHL players, whether that be in moves to win right away or as part of more minor deals.
Over the past 15 years, the Chicago Blackhawks traded away eight draft picks (in seven deals) that have turned out to be either very solid NHLers or are well on their way.
All of these picks were dealt by former general manager Stan Bowman. They eventually were used by other teams to select players that could have been very useful to Chicago.
Since taking over in October 2021, current Blackhawks GM Kyle Davidson and his staff have been more astute at acquiring, stockpiling and managing draft assets.
Blackhawks Dynasty Era
The Blackhawks "Dynasty Era" ran between the 2009-10 and the 2016-17 seasons when they won three Stanley Cups and were at or near the top of the regular-season standings. Led by Patrick Kane, Jonathan Toews and Duncan Keith, this was a time when Chicago was trying to win and generally succeeded.
Brock Nelson
Four trades in particular involved draft picks being moved, then those draft slots resulted in some very good players being selected later by other clubs.
The first came in the summer of 2010 right after winning the Stanley Cup when Bowman thought it was OK to move down five spots from 30th to 35th and acquire a 58th overall pick on top of that from the New York Islanders.
At the time it seemed harmless, but any shift in positions in the draft could have lasting effects. The Islanders drafted forward Brock Nelson with that 30th overall pick in 2010 while the Blackhawks selected forward Ludvig Rensfeldt and goalie Kent Simpson. If you've never heard of either of them, that's because Rensfeldt never signed a contract and has only played in Sweden. Simpson started one NHL game, allowing six goals.
Nelson has 275 goals and 531 points in 840 career NHL regular season games to go along with 26 goals and 48 points in 77 playoff games. He broke into the league in 2013-14 and is still a major contributor for the Islanders.
Igor Shesterkin
The Blackhawks could have had Vezina Trophy winner Igor Shesterkin, but traded the pick to send him to the Islanders as well in 2014. He was drafted in the fourth round, so there's no way of telling what a mid-round pick could turn into. The return the Blackhawks got was very poor when we look back.
Chicago received Peter Regin and Pierre-Marc Bouchard. While Regin played a total of 21 games for the Blackhawks before heading overseas, Bouchard finished that season in the AHL and also headed overseas.
Shesterkin ended up being drafted by the New York Rangers. He would have lined up perfectly for the Blackhawks. Corey Crawford's last season was in 2019-20 and Shesterkin's rookie season came in the same year as a backup. He could've had one year of mentorship under Crawford like Shesterkin did under Henrik Lundqvist and then taken over.
Christian Dvorak
Another one of these impactful trades didn't happen until nearly four years later when the Blackhawks acquired David Rundblad and Mathieu Brisebois from the Arizona Coyotes for a second-round pick in 2014. That pick turned into Christian Dvorak.
The centerman has had a solid career as a middle-six player, splitting time between the Coyotes and now the Montréal Canadiens. Dvorak has 93 goals and 216 points in 452 games, but is great in the faceoff circle and provides secondary scoring. In the bottom-six for the Blackhawks at the time, he could have been useful before injuries started to derail his career.
Rundblad ended up playing 63 games for the Blackhawks, scoring three goals and 16 points, but left the NHL in 2016. Brisebois never even came close to playing in an NHL game.
Alexander Romanov
In the final year of what should be considered the Blackhawks dynasty, the team sacrificed youth to get what they thought would help before the trade deadline in 2016. This trade involved sending forward Phillip Danault and a second-round pick that turned into Alexander Romanov to Montréal in return for Tomas Fleischmann and Dale Weise. These two players combined for four goals and six points in 34 games for Chicago.
Not only did Danault turn into a very good two-way center, Romanov is a strong top-four defenseman now on the Islanders. The future is bright on defense in Chicago, but the team would've had a shutdown defender for a number of years already.
Still Holding Onto Hope
Jake Oettinger
Immediately after the 2016-17 season, things went downhill for the Blackhawks, but they still held onto hope that most of their core could get the job done again. In order to restock the farm and gain a draft pick, Bowman chose to trade down from 26 to 29 in the 2017 draft and also receive a third-round pick for doing so from the Dallas Stars.
The pick that the Blackhawks gave up to get two later selections turned into goalie Jake Oettinger. Meanwhile, Chicago selected Henri Jokiharju and Andrei Altybarmakyan. Jokiharju has had a pretty solid career thus far and was traded to the Buffalo Sabres at a later date.
Oettinger has turned into one of the league's top netminders on a strong Dallas team. He was hampered by a lower-body injury this season, but is 113-48-23 in his career with a 2.51 goals-against average and .913 save percentage. Once again this is an example of why trading down in the first round isn't such a good idea.
Spencer Stastney
In 2018, the Blackhawks were selling at the deadline and traded Ryan Hartman to the Nashville Predators along with a fifth-round pick. Coming to Chicago was Victor Ejdsell, a first-round pick, and a fourth-round pick.
The Blackhawks did get some good value because they drafted forward Philipp Kurashev with the fourth-rounder in 2018. But Spencer Stastney was the talented defenseman the Predators selected with the fifth-round 2018 pick the team gave up.
Stastney is just breaking into the NHL now and the trade ultimately did work out for the Blackhawks. But Stastney is expected to be a great piece in Nashville in the coming years.
Cole Sillinger and David Jiricek
The Blackhawks were still not giving up on competing, and went out in July 2021 and acquired Seth Jones from the Columbus Blue Jackets along with the 32nd overall pick in 2021 and a sixth-round pick in 2022. What the Blackhawks gave up would have been great pieces to have right now in the midst of a rebuild. Shipped off was Adam Boqvist, the 12th overall pick in 2021, a second-round pick in 2021, and a first-round pick in 2022 (sixth overall).
Two of these picks have turned into very talented young players in Cole Sillinger and David Jiricek. Both of their careers are at the very beginning and are expected to be long and successful while Jones, the main piece coming back, is 29 years old.
Jones just finished the second year of an eight-year $76 million contract extension. He is by far the Blackhawks minutes leader on defense and anchors a promising young core of blueliners. But Jones also hinted he's not totally happy playing on a rebuilding team that's far off from winning again.
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