5 Draft Day Regrets From Red Wings’ Last 10 Drafts

The Hockey Writers

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 10 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?

2009 Draft – Landon Ferraro

After not having a first-round pick in the 2009 Draft, the Red Wings selected the number 18-ranked North American skater in Landon Ferraro with their second-round pick at number 32. After being touted as having the knack for goal-scoring and being a solid two-way center, there were hopes that he could become one of the Red Wings’ building pieces for the future at the center position.

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This never materialized as Ferraro struggled to crack the Red Wings lineup in his time with the organization which spanned three seasons from the 2013-14 season to the 2015-16 season before being placed on waivers by the team in November 2015 and being claimed by the Boston Bruins. In total, Ferraro played 17 games for the Red Wings and tallied one single assist.

The pick directly after the Red Wings’ selection of Ferraro was Ryan O’Reilly by the Colorado Avalanche. While O’Reilly was ranked lower than Ferraro at the number 39 ranked North American skater in the 2009 Draft, his career has seen a completely different trajectory and success than Ferraro. He has played in nearly 1,000 career NHL games over 14 seasons in the league with a total of four teams (Colorado Avalanche, Buffalo Sabres, St. Louis Blues and Toronto Maple Leafs).

Ryan O'Reilly St. Louis Blues
Ryan O’Reilly could have been a Red Wing in the 2009 Draft. (Amy Irvin / The Hockey Writers)

O’Reilly developed himself into one of the league’s better two-way forwards, winning the Selke Trophy for best defensive forward for the 2018-19 season and also the Lady Byng Memorial Trophy for sportsmanship and “gentlemanly” play in the 2013-14 season.

He played a vital role in the Blues’ Stanley Cup winning season in 2018-19, leading the team with 23 points in 26 playoff games en route to the Conn Smythe Trophy, and was an integral piece of the Blues’ lineup and success, having held the captaincy role for three seasons from 2020-21 to 2022-23 before being traded to the Maple Leafs in February 2023.

To date, he has played in 991 regular season games while tallying 256 goals, 446 assists and 702 total points on top of playing in 75 playoff games with 65 total points.

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 October 2017.

Five picks after the Red Wings selected Sheahan, the Washington Capitals picked Russian forward Evgeny Kuznetsov at pick 26 and he has become one of the Capitals’ most durable and reliable players. While he’s missed games the past few seasons, Kuznetsov has missed only 36 regular season games over the nine seasons he has been in the NHL.

Related: Ranking the Detroit Red Wings’ Last 20 Draft Classes

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He has been 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. He ranks ninth in points (67) and fourth in assists (38) in the entire league since the 2014-15 season in the playoffs as well.

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 that 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.

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 159 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 off of a solid rookie season in 2018-19 where he totaled 20 points in 52 games played.

Dennis Cholowski Detroit Red Wings
Dennis Cholowski, Detroit Red Wings (Amy Irvin / The Hockey Writers)

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.

The past two seasons, he has had break-out seasons with the Sabres, totaling 68 points in the 2021-22 season and then making the jump to 94 points last season. He has also become one of the league’s most potent powerplay goal-scorers, tallying 20 last season which ranked third in the league. On top of that, he led the league in hat tricks with three.

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 301 games between St. Louis and Buffalo, tallying 103 goals, 94 assists and 197 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 powerplay) and 68 total points.

Filip Zadina Detroit Red Wings
Filip Zadina was never able to live up to the hype and expectations for the Red Wings (Amy Irvin / The Hockey Writers)

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) 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 283 games for the Canucks and compiled 26 goals and 215 assists for a total of 241 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.

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