Revisionist history can be fun, but it can also be very, very painful. This particular example relates to the Toronto Maple Leafs during the Brian Burke "truculence" era, but it's not one of the main moves that you hear discussed, such as the Tyler Biggs pick or the trade for Phil Kessel that ended up costing the Leafs Tyler Seguin AND Dougie Hamilton.
In the summer of 2008, the Leafs drafted highly touted, roughneck defender Luke Schenn with the 5th overall pick in the draft. Now, that draft itself had fallen off quite a bit after the first 4 picks, and the Leafs would have been unlikely to reach far back enough to select Erik Karlsson, Jordan Eberle, John Carlson or Roman Josi, but just one year later, Burke had a chance to make a franchise altering move involving Schenn which would have changed the landscape in Toronto for (presumably) the next 15-20 years.
The Tampa Bay Lightning owned the #2 overall pick in the 2009 NHL Entry Draft, using that pick to select hulking Swedish defenseman Victor Hedman. Renowned as one of the league's most elite defenders over the last decade, Hedman is a Norris Trophy and Conn Smythe winning defenseman, who also happens to have two Stanley Cup rings. At the time of the draft, however, he could have been a Leaf.
According to Chris Johnston, longtime trusted NHL Insider with Sportsnet, who is now with TSN, Brian Burke had the opportunity to snag the #2 pick in 2009 and all it would have cost him was Luke Schenn.
This is where it's easy to look back and condemn Burke for making one of the worst decisions in modern hockey history, but it's worth noting that, at the time, Luke Schenn was believed to be the next elite bruising defenseman. Hedman, while highly touted, was a Swedish prospect who had never played on North American ice. There were some question marks, and Burke certainly did not have the luxury of knowing then what we all know now.
A quick comparison of their NHL careers will show Schenn, an 868-game NHL veteran, managing just 161 points over that span. Meanwhile, his counterpart Hedman has played in 862 games, registering 565 career NHL points, with an additional 88 points in 132 games of playoff experience.
Obviously, had the Leafs made the swap, Hedman would likely be the Leafs' captain now, and we would not have the luxury of having the embarrassment of offensive riches that we are currently enjoying in Auston Matthews, Mitch Marner, John Tavares and William Nylander, but it's fun to wonder what the team would have looked like built around an absolute stallion like Victor Hedman. Would the Leafs have challenged for a Stanley Cup over the last 10-12 years at any point? Who knows? But it's certainly something worth pondering.