Toronto Maple Leafs Draft Retrospective: The dynasty that could have been

The Toronto Maple Leafs multiple playoff failures have brought a lot of talk about changing the core of the team. This got us thinking. How might the Leafs look different had they selected other players during the draft years of their core players?

The drafting that the Toronto Maple Leafs did after the first round in the years where they also drafted Auston Matthews, Mitch Marner, William Nylander, and Morgan Rielly was objectively bad. Had they done better, they likely would have won a Stanley Cup by now.

For this exercise, first let's outline some parameters. Hindsight being 20/20, of course, every team in the NHL would love to correct mistakes they made at the draft table. All teams can look back with regret about players they didn't take.

Second, this is for entertainment purposes only. Assuming a team's evaluation of teenagers will not come without oversights is completely unrealistic.

Lastly, this retrospective of the Leafs recent drafts will only look at players that they took versus players that were still available and could have been selected at that draft position. In other words, picks that the team traded away and used by another club were not evaluated.

Also, the Leafs team needs at each particular draft slot were not taken into account. In our retrospective, they simply took the best player available.

The 2012, 2014, 2015, and 2016 NHL drafts will be recalibrated. These are the drafts where the Leafs selected their core players. John Tavares was added as a free agent so he is not considered here.

Morgan Rielly, William Nylander, Mitch Marner, and Auston Matthews were the players the Leafs selected with their first-round picks during each of these drafts.

We will review if the Leafs choosing them was the proper choice in hindsight. For each of those respective drafts, we will also look at other selections the Leafs made and what notable players were available. Did the Leafs make the right choice? If not, who should they have taken?

Without further ado, let's begin our look back and analysis of these drafts, starting with the 2012 NHL Draft. (Note: all draft statistics courtesy of hockeydb.com.)

Revisiting the 2012 NHL Draft

In the 2012 NHL Draft, the Toronto Maple Leafs selected Morgan Rielly with the 5th overall pick. He has outlasted all of the picks taken ahead of him in the draft. He has already clinched the best career of the top five selections.

Other notable Leafs' picks included D Matt Finn from the Guelph Storm in Round 2 at 35th overall, Dominic Toninato in Round 5 at 126th overall, and Connor Brown in Round 6 at 156th overall.

Now, let's look at where other notable NHL players were selected in this draft. At 19th overall, the Tampa Lightning took goalie Andrei Vasilevskiy. During Round 3, Chandler Stephenson was taken with the 77th pick by the Washington Capitals. Later that round, Colton Parayko went 86th overall to the St. Louis Blues.

This was also the draft where the Winnipeg Jets selected goaltender Connor Hellebuyck. He was taken in Round 5 at 130th overall.

What is our hindsight analysis of this draft? Rielly's career has easily surpassed those taken ahead of him and he has been everything the Leafs could have asked for.

Yet, with Vasilevskiy, the Leafs could have drafted the best goalie of this generation. Instead of drafting FInn, in our retrospective, the Leafs take Colton Parayko to play defense on the right side. Our draft do-over also sees the Leafs take Hellebuyck instead of Toninato.

What is the net result of our 2012 Leafs' draft? The Leafs no longer have Rielly playing defense, but a goalie tandem in Vasilevskiy and Hellebuyck that rivals Terry Sawchuk and Johnny Bower. Parayko now slots into the Leafs top 4 defensemen.

The 2014 NHL Draft: Do The Leafs Still Take William Nylander?

In the 2014 NHL Draft, the Leafs selected William Nylander with the 8th overall pick in Round 1. In Round 3 they took Rinat Valiev at 68th overall. Other Leafs' picks included: J.J. Piccinich (R4, 103), Dakota Joshua (R5, 128), Nolan Vesey (R6, 158), and Pierre Engvall (R7, 188).

Who were the other notable NHL players taken in this draft? David Pastrnak was selected 25th overall in the first round by the Boston Bruins. Brayden Point came to the Tampa Bay Lightning in the third round with the 79th overall pick. In Round 4, Devon Toews was taken 108th overall by the New York Islanders.

What is our analysis of the Leafs' 2014 NHL Draft? Nylander's stock is rising and he might someday reach fifty goals in a season. Pastrnak has already done that. He has consistently performed better over the years. Welcome to Toronto, David!

At pick number 68 in Round 3, the Leafs say goodbye to Valiev. The choice now becomes Point. With pick 103 in Round 4 of our retrospective the Leafs now take Devon Toews to help further solidify their defense.

What is the net result of the Leafs' 2014 NHL Draft? Point now joins forces with Auston Matthews to provide the Leafs with a formidable duo up the middle for years to come. Toews brings some grit and offense to our continued makeover of the Leafs' defensemen.

2015 NHL Entry Draft

In Connor McDavid's draft year, the Leafs had the 4th overall pick in the first round. Mike Babcock, then head coach of the team, loved defenseman Noah Hanifin (5th overall to the Carolina Hurricanes). The Leafs, however, correctly chose winger Mitch Marner from the London Knights.

The Leafs draft haul that year also included: Travis Dermott (R2, 34), Jeremy Bracco (R2, 61), Andrew Nielsen (R3, 65), Martins Dziekals (R3, 68), Jesper Lindgren (R4, 95), Dmytro Timashov (R5, 125), Stephen Desrocher (R6, 155), and Nikita Korostelev (R7, 185).

Other notable NHL players selected in Round 1 of this draft also included Timo Meier to the San Jose Sharks at 9th overall, Mikko Rantanen to the Colorado Avalanche at 10th overall, and Matthew Barzal to the New York Islanders at 16th overall.

Things get interesting with this draft in Round 2 and beyond. Sebastion Aho went 35th overall to the Hurricanes. Anthony Cirelli was selected in the third round with the 72nd pick. Kirill Kaprizov was a steal for the Minnesota Wild during Round 5 with the 135th pick. Andrew Mangiapane was taken in Round 6, 166th overall, by the Calgary Flames.

In our draft do-over, the Leafs still take Marner at 4th overall. It was the correct choice then and still is. He remains with the Toronto Maple Leafs. With their third-round picks at 61, 65, and 68 the Leafs (again with the benefit of hindsight) take Kaprizov, Cirelli, and Mangiapane.

The Leafs' net result of our 2015 draft retrospective? The team now drafts Aho with the 34th overall pick, instead of Dermott. Kaprizov now becomes another sniper added to the lineup. Cirelli becomes the Leafs' third-line centre. In this alternate universe, his checking of Auston Matthews in the playoffs now doesn't have a chance to happen since they are teammates.

The 2016 NHL Draft: Matthews remains with the Leafs

The Leafs won the 2016 NHL Draft Lottery and with it the right to select Auston Matthews with the first overall pick. He is by far the best NHL player taken in this draft. The Leafs made the correct call here.

This year their other picks were Egor Korshkov (R2, 31), Carl Grundstrom (R2 57), Joseph Woll (R3, 62), J.D. Greenway (R3, 72), Adam Brooks (R4, 92), Keaton Middleton (R4, 101), Vladimir Bobylev (R5, 122), Jack Walker (R6, 152), Nicolas Mattinen (R6, 179), and Nikolai Chebykin (R7, 182).

Notable NHL players selected in this draft were Alex Debrincat at 39th overall to the Chicago Blackhawks. Adam Fox went 66th overall to the Calgary Flames. Ross Colton went 118th to the Lightning and Jesper Bratt went 162nd to the New Jersey Devils.

In our draft do-over, Matthews remains a Leaf with the first overall pick, but DeBrincat is picked at number 31 in Round 2. Since Fox is still available he becomes a Leaf with pick number 62 in Round 3. Woll is no longer needed since the Leafs are set in goal from the 2012 draft.

The Leafs now take Bratt and Colton with picks number 72 and 92 overall.

The Leafs result after the 2016 NHL Draft do-over? Matthews remains the Leafs' number one centre. Woll is no longer with the Leafs as a homegrown goalie. Perennial Norris trophy candidate Fox is now the Leafs number one defenseman. Debrincat is added to the top six at forward. Colton and Bratt are now useful third-line players for the Leafs.