Every team has made picks in a draft that when they look back at who they picked compared to who was available, they think “Maybe we should have taken this guy instead.” Over the last 15 NHL Drafts, the Detroit Red Wings fall into that mindset with a few different picks they have made. So, what are five picks they wish they could redo?
2010 Draft – Riley Sheahan
In the following draft, the Red Wings selected Notre Dame forward Riley Sheahan with their first-round pick at number 21. His most notable contribution as a Red Wing is being known as the last player to score a goal at Joe Louis Arena. He was never able to live up to the expectations of a first-round pick and spent seven seasons with the team, only compiling 98 points in 292 total regular season games from 2011-12 to 2017-18 before being traded to the Pittsburgh Penguins in Oct. 2017.

Five picks after the Red Wings selected Sheahan, the Washington Capitals picked Russian forward Evgeny Kuznetsov at pick 26 and he became one of the Capitals’ most durable and reliable players.
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He was one of the most consistent players for the Capitals during their playoff runs as well, helping lead the way in the 2020 Playoffs when they won the Stanley Cup. He led the team with 32 points in 24 playoff games for the Capitals en route to the Cup win.
2011 Draft – Tomas Jurco, Xavier Ouellet & Ryan Sproul
With three picks in the second round of the 2011 Draft, the Red Wings selected three players who only totaled 69 points in 328 games as Red Wings players. On top of the Red Wings, the entire league passed on one player that they wished they would not have. That player was picked at number 58 by the Tampa Bay Lightning in Nikita Kucherov.
The three players the Red Wings took in the second round, Tomas Jurco (35th overall), Xavier Ouellet (48th overall) and Ryan Sproul (55th overall) never lived up to the expectations bestowed upon each of them. Jurco led the way for the trio, tallying 69 total points in 159 games played, after not being able to turn his skill set into anything solid for the Red Wings organization.
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On the flip side, Kucherov’s development has turned him into one of the league’s most prolific offensive forces when he is healthy. Since making his NHL debut in the 2013-14 season for the Lightning, he has earned numerous accolades, including being a four-time All-Star (2017-19, 2023) and winning the Art Ross Trophy (most points), Hart Trophy (league MVP) and the Ted Lindsay Award (most outstanding player as voted on by the NHL Players Association) after the 2018-19 season.
The success Kucherov has had does not stop when the regular season ends, being the league leader in playoff points since the 2014-15 season with 171 while helping the Lightning win back-to-back Stanley Cups in 2020 and 2021.
2016 Draft – Dennis Cholowski
In the 2016 Draft, the Red Wings selected defenseman Dennis Cholowski with their first-round pick in hopes that he would be part of the defensive core for years to come with his excellent skating and offensive mind. It never happened, with Cholowski not being able to build on a solid rookie season in 2018-19 where he totaled 20 points in 52 games played.

His offensive game never translated to the NHL, along with his defensive game not developing as hoped either. He played in 104 regular season games and tallied a total of 47 points as a Red Wing before being left exposed in the 2021 Expansion Draft for the Seattle Kraken, being taken as their selection from the Red Wings.
Six picks later, the St. Louis Blues drafted UConn forward Tage Thompson with their selection. While only spending one season with the Blues before getting traded to Buffalo in a deal for O’Reilly in 2018, Thompson has developed into one of the league’s best up-and-coming players.
He has become one of the league’s most potent power-play goalscorers, tallying 42 during his time with the Sabres.
His development has led to being one of the cornerstone pieces for a rebuilding Sabres team, and he was rewarded with a seven-year contract extension in 2022. Overall, Thompson has suited up for 448 games between St. Louis and Buffalo, tallying 176 goals, 149 assists and 325 points.
2018 Draft – Filip Zadina
Heading into the 2018 Draft, many believed that forward Filip Zadina was a sure-fire top-three pick due to his explosive shot and offensive play. So when he was available when the Red Wings were picking at number six, they thought they had found a steal in the draft. The expectations for Zadina were that his skill set would translate to the NHL level and he could be an elite level goal-scorer. That never happened, with him struggling to put together a full season of production even with showing glimpses of what made him one of the top prospects of the 2018 Draft. Overall, he played in 190 games for the Red Wings from the 2018-19 season until he was released following the 2022-23 season and totaled only 28 goals (12 of which were on the power play) and 68 total points.

The pick immediately following the Red Wings’ selection of Zadina ended up with the Vancouver Canucks adding a cornerstone defenseman to their roster in Quinn Hughes. Leading up to the draft, there were concerns about Hughes’ size and strength not being able to withstand the NHL, but that has not been the case as he has developed into one of the NHL’s best young defensemen since entering the league in the 2018-19 season. He finished second behind the Colorado Avalanche’s Cale Makar in the voting for the Calder Trophy (league’s best rookie) before winning the award in 2023-24 and is now the leading force on the backend for the Canucks.
With an increased development in the defensive zone and continued success with his offensive game, Hughes earned All-Star honors in 2020 and also finished fifth in the league in assists last season. Overall, he has suited up for 427 games for the Canucks and compiled 59 goals and 346 assists for a total of 405 points.
In general, there are always picks that teams look back on and think of what could have been. These picks are no different and make fans wonder what would have happened if the Red Wings management team had taken the above-listed players over who they actually took.
