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Charlie AI explains the draft choice process

 

ok, go slowly here. Presume that the Leafs are in the bottom 5. Tell me what happens now

Alright David—let’s walk through this slowly and clearly, step by step, assuming the Toronto Maple Leafs finish in the bottom 5.

🧭 Step 1: Season ends

The Leafs finish, say:
👉 4th worst team in the NHL

That’s important because:

  • They are in the lottery
  • They have good odds, but not the best

🎰 Step 2: Lottery happens

All 16 non-playoff teams are entered.

Two draws take place:

  • One for 1st overall pick
  • One for 2nd overall pick

📊 Step 3: Leafs’ position going into lottery

Because they’re 4th worst:

  • They have a meaningful chance at #1
  • But 3 teams have better odds

🎲 Step 4: What can happen (3 simple outcomes)

🥇 Scenario A: Leafs WIN the lottery

  • They get 1st overall pick
  • Best possible outcome

👉 This is the “jackpot”

🥈 Scenario B: Leafs move up a bit

  • They might win 2nd overall
  • Or move up slightly depending on results

👉 Still excellent outcome

📉 Scenario C: Leafs don’t win

Then:

  • Other teams jump ahead of them

Because only 2 teams can move up:

👉 Leafs can fall from 4th → maximum 6th overall

🔒 Step 5: Your “range” is locked in

As a bottom-5 team:

👉 Leafs will draft somewhere between:

  • 1st overall (best case)
  • 6th or 7th overall (worst case)

🧠 Step 6: Why this is still very good

Even if they fall:

  • They still get a top prospect
  • Likely a future core player

🧾 Simple example

Let’s say:

  • Leafs = 4th worst

Lottery result:

  • Team ranked 7th wins #1
  • Team ranked 10th wins #2

Now:

  • Those teams jump ahead

Leafs drop:
👉 from 4th → 6th overall

🏁 Final takeaway

If the Leafs are bottom 5:

👉 They are in a very strong position

They will:

  • have a real shot at #1
  • be guaranteed a high pick
  • but cannot control the outcome

If you want next step, I can show you:

  • the actual odds for each slot (1st–5th worst)
  • or simulate what happens in a real lottery draw (very helpful to visualize it)
yes

Perfect—let’s make this very concrete with a simple simulation so you can see it happen.

We’ll assume the Toronto Maple Leafs finish 4th worst.

🎯 Starting point (before lottery)

Rankings (worst → better):

  1. Team A (worst)
  2. Team B
  3. Team C
  4. Leafs 👈
  5. Team D
    … (and so on)

🎰 Step 1: Lottery draw for 1st overall pick

Let’s say:
👉 Team C (3rd worst) wins

So now:

  • Team C jumps to #1 overall

🎰 Step 2: Lottery draw for 2nd overall pick

Now another draw happens.

Let’s say:
👉 Team D (5th worst) wins

So now:

  • Team D jumps to #2 overall

📊 Step 3: Now we rebuild the draft order

Top 2 picks are now locked:

  1. Team C
  2. Team D

Now we place the rest based on original standings:

  • Team A (was worst) → now picks 3rd
  • Team B → picks 4th
  • Leafs (4th worst) → now pick 5th

📉 Final result for Leafs

👉 Leafs drop from 4th → 5th overall

🧠 Another quick scenario (better outcome)

Let’s reset.

Step 1:

👉 Leafs WIN lottery

They jump to:

  • #1 overall

Done—best case.

😬 Worst-case scenario

Let’s simulate the worst possible outcome.

Step 1:

Team ranked 8th wins #1

Step 2:

Team ranked 10th wins #2

Both jump ahead.

Now Leafs drop:

👉 from 4th → 6th overall

📊 Your full range (this is the key insight)

If Leafs are 4th worst:

👉 They will draft:

  • Best case: #1 overall
  • Worst case: #6 overall

🏁 Simple way to think about it

Being bottom 5 means:

  • 🎟 You’re holding a strong lottery ticket
  • 📉 But you can still slide a bit
  • 🏒 You’re guaranteed a top-tier prospect

🔥 The takeaway

You’re not guaranteed Connor Bedard…
but you’re guaranteed to be in the conversation.

If you want, next step I can:

  • show the actual % odds for each position (1st–5th worst)
  • or run a few more “realistic” simulations so you see patterns (very helpful)

Alright David—let’s go just as slowly for this one.

Now assume the Toronto Maple Leafs finish 6th worst.

🧭 Step 1: Where they stand

They are:
👉 6th worst team

So:

  • Still in the lottery
  • But weaker odds than bottom 5

🎰 Step 2: What they can win

Because of the NHL rules:

👉 A team can only move up 10 spots

So:

  • 6th worst → can still win #1 overall
  • No restriction here yet

🎲 Step 3: The 3 possible outcomes

🥇 Scenario A: Leafs win the lottery

  • They jump to #1 overall

👉 Still possible—but less likely than bottom 5 teams

🥈 Scenario B: Leafs move up to #2

  • They win the second draw
  • Get #2 overall

📉 Scenario C: Leafs don’t win

Now this is where position matters more.

Other teams jump ahead.

📊 Step 4: How far can they fall?

Because:

  • Only 2 teams jump up

👉 Leafs (6th worst) can drop to about:

8th overall (worst case)

📉 Example

Starting:

  • Leafs = 6th worst

Lottery:

  • Team ranked 9th wins #1
  • Team ranked 11th wins #2

Now:

  • Both jump ahead

Leafs drop:
👉 from 6th → 8th overall

📊 Final range

If Leafs are 6th worst:

👉 They will draft between:

  • #1 overall (best case)
  • #8 overall (worst case)

🧠 Why this is noticeably worse than bottom 5

Compared to 4th or 5th worst:

  • Lower odds of winning
  • Can fall further
  • Less likely to land elite top-3 talent

🏁 Bottom line

6th worst is still good…
but you’re now on the edge of the premium zone

You still have a shot—
but you’ve lost that strong “top 5 advantage.”

If you want, I can now show you:

  • the actual percentage odds difference between 5th vs 6th (it’s bigger than most people think)
yes

I’m checking the current NHL lottery odds so I can compare 5th-worst versus 6th-worst accurately and not rely on stale numbers.

Yes — the drop from 5th worst to 6th worst is real, but it is not huge.

Using the current NHL lottery structure, the team finishing 5th worst has an 8.5% chance to win the first lottery draw, while the team finishing 6th worst has a 7.5% chance. The league’s lottery still uses two drawings, and no team can move up more than 10 spots.

So, in plain terms:

If the Leafs finish 5th worst, they are in a slightly stronger lane. They have better odds at the top pick, and they are still squarely in that “premium zone” where fans start paying close attention to lottery position. If they finish 6th worst, they are still very much in the mix, but the odds soften a bit.

The reason people talk about the bottom 5 is not that the rules suddenly change at No. 5. There is no special legal line there. It is more that the odds begin to taper as you move down the order. In the current table, the first six spots are 18.5%, 13.5%, 11.5%, 9.5%, 8.5%, and 7.5% for the first lottery draw. That means 5th worst still sits in a visibly stronger tier than 6th worst, even though both remain viable lottery positions.

The other key point is this: because the NHL lottery determines the top spots through two draws, and because teams can jump only 10 places, a team finishing 5th worst or 6th worst still has a pathway to the very top, but the closer you are to the bottom, the better your mathematical leverage. Only the top 11 seeds are eligible to move all the way to No. 1.

So the clean takeaway is:

5th worst: better odds, still in the stronger top-lottery group.
6th worst: still good, but a noticeable step down.

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The Evolution of the Leafs: Toronto Blueshirts – Arenas – St. Pats – Leafs

The Toronto Blueshirts

I am betting big on what the T stands for.

Prior to the NHL, there was a league known as the National Hockey Association. It was founded in 1910 and continued until the NHL’s formation in 1917.

The initial teams were the Montreal Shamrocks, the Montreal Wanderers, the Renfrew Millionaires and also teams from Cobalt, and  Haileybury, unlikely now sites to be on the radar for NHL expansion.

The  first Toronto franchise in this league became the Toronto Blueshirts. Their home rink was the Mutual Street Arena.

The Blueshirts were the first Toronto team to win the Stanley Cup in 1914, defeating the Victoria Aristocrats. It was then a true challenge cup, as it was intended. 1

By 1914, the remaining teams in the league consisted of the Montreal Canadiens, the Quebec Bulldogs, the Ottawa Senators and the Montreal Wanderers.

Key players included Scotty Davidson, who died in WWI, Harry Cameron, the Bobby Orr of the day, Frank Foyston and Jack Marshall.

Eddie Livingstone

Eddie looks like a decent chap to me.

 

The Blueshirts team was owned by a gentleman by the name of Eddie Livingstone who was quite controversial. He was often in disputes with the other owners. He aggressively signed players away from other teams, particularly Montreal and Ottawa. The League issued suspensions to these players, challenged the contracts and attempted to block other signings. Livingstone sued them multiple times.

Toronto Shamrocks

This photo was likely taken later in the day on March 17th.

 

The Shamrocks were a short-lived team in the NHA from 1912 to 1915. They also played out of the Mutual Street Arena. The team struggled due to poor attendance. By 1914, it was bankrupt. Enter Eddie. He bought the remnants of the team and now owned two teams in the NHA, much to the chagrin of the other owners, who were legitimately concerned about conflict issues.

Eddie maintained the League’s articles did not deny the right to multiple franchises.

By 1915, even Eddie realized that this idea was not working well. The players preferred to be with the Blueshirts, costs were excessive and the fights with the other owners were distressing. Eddie discontinued operation of the team but he held onto the franchise title, which upset the other owners.

Toronto Arenas

Champions of the World might be a bit of an overstatement. They did win Lord Stanley’s Cup in 1917. The bottom left photo references the O’Brien Cup which was the trophy given to the top NHA team. The Stanley Cup was still a challenge cup, given to the winner of, oddly enough, the challenge. They played the winner of the Pacific Coast League for this award.

During WWI, the League loaned several Toronto players to other teams on the understanding that they would return to Toronto. Livingstone insisted the players be returned. Ottawa and Montreal refused to do so. Livingstone accused them of theft. The League asserted that he had mismanaged his team. This became the final straw.

The other owners tried to expel him from the league, buy him out, and refuse to return his players. Livingstone launched legal proceedings for injunctive relief.

In 1917, they decided to start a new league and ban him from membership.

Hence, the NHA dissolved, leading to the creation of the NHL in 1917.  Livingstone sued, of course, but his legal claims were, for the most part, unsuccessful.

For a more complete review of Eddie’s lawsuits and the demise of the NHA, see the story of “Deceptions and Doublecross: How the NHL Conquered Hockey”, written by Morley Holzman and Joseph Nieforth, 2002, Dundurn Press.

The prior contracts of the Blueshirts players were apparently assigned to a new Toronto franchise, then designated as temporary. 2 It was a temporary admission as the fourth team, the Quebec Bulldogs, were unable to play that season. The team was then called the Toronto Arenas, not a particularly noteworthy name. The Arenas did win the Stanley Cup in 1917.

The Toronto St. Pats

Gotta love the tie on the coach. And why is the goalie not in front ?

 

If a fight breaks out, I want to be on their side.

 

4 coaches ? or maybe a “get over here for the photo” moment ?

The team was sold in December of 1919 to Charles Querrie, who changed the name to Toronto St. Patricks. Toronto then had a strong Irish Catholic community, particularly in neighbourhoods close to the Mutual Street Arena, such as Cabbagetown, Corktown, St. Mary’s Parish and near St. Michael’s Cathedral. The chosen name was intended to align the team with this ethnic group to build fan support. It was successful as the fan base grew significantly.

The Leafs

In 1927, the team was sold to Conn Smythe and his associates and rebranded as the Toronto Maple Leafs, as of February 17, 1927.

There had been a baseball team in Toronto since 1886 called the Toronto Maple Leafs. It played in the International League as a AAA team.

Smythe’s public statement was that he wanted a name which symbolized Canada and that that he had admired the Maple Leaf Regiment he had commanded in WW1. This was likely a factor, no doubt, but the popularity of the baseball team was likely very influential. This raises another issue about trademarks and all that, but let’s leave this for now.

The Morality Show

The NHL was hence formed in controversy, by a conspiracy to cut out the person designated as an evil force.

The establishment of the Stanley Cup as the ultimate trophy is equally controversial as it was a clear violation of the initial trust created by Lord Stanley, when he was the Governor-General of Canada. 3

The theme of corruption continued. The Norris brothers, well step-brothers, owned competing franchises in Detroit and Chicago through the 1950’s and 1960’s.

Ballard bought controlling interest of the Leafs by selling the shares of the deceased Conn Smythe to himself as he was the executor of the will. He did so at a value well lower than market value.

The grocery magnate, Steve Stavro, did the same on Ballard’s death. He sold the controlling interest to himself as the executor of Ballard’s estate. He was sued successfully by the “residual legatees”, that is, those beneficiaries at the bottom of the list. But really, did he care? He got ownership of the team and paid out the settlement from the profits.

Our Pal Hal also was sentenced to three years in Her Majesty’s Custody for using the funds of  a public company, that is, the Toronto Maple Leafs, to renovate his summer home on Georgian Bay.

 

 

 

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Syl Apps et al

Syl Apps

 

Frank Mahovlich #27, Syl Apps #10, Lionel Conacher #9, King Clancy #7, Hap Day #4, Turk Broda #1 , Ace Bailey #6

King Clancy
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Time to Think This Over (again for the 57th time)

Well. it has been a while since the last parade on Bay Street. My shrink has advised that the bandage must be ripped off with a clean swipe. I have honestly had enough. It is bad enough when I am too stressed out to watch the actual live game but now it has become a serious mental illness.

In 2013, the Leafs came back from a 3-1 series deficit, only to tie it up and then sink the whole ship when winning game 7, 4-1 yet, with 8 minutes left. That left emotional scarring.

Now in 2024, Nylander has concussion protocol and Matthews has food poisoning …huh ? truly this team is cursed.

In 2025, the number one goalie is out on concussion protocol in game 2. Huh ?

Hence, my application for the bandwagon membership. I promise to cheer appropriately, actually have the stamina to watch the games live, (not for years have I been stable enough to watch the Leafs in real time) and even get  Brock whomever jersey and follow semi-religiously.

I await, with some degree of trepidation, your decision on admission, prepared to accept whatever indignity that this may entail.

D.

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2003 Playoffs

 

The Philadelphia Flyers finished as the fourth seed in the Eastern Conference with 107 points. The Toronto Maple Leafs finished as the fifth seed in the Eastern Conference with 98 points. This was the fifth playoff meeting between these two teams with Philadelphia winning three of the previous four series. They last met in the 1999 Eastern Conference Quarterfinal, which Toronto won in six games. The teams split this year’s four game regular season series.

The Flyers defeated the Maple Leafs in seven games. In game one, Alexander Mogilny scored a hat trick to give Toronto a 5–3 victory.[17] The Flyers responded to the loss with a 4–1 win in game two with John LeClair, Mark Recchi, and Simon Gagne all contributing a goal and an assist.[18] In game three, Toronto came back from an early two-goal deficit to win the game in double overtime on a goal by Tomas Kaberle, his second of the game.[19] Game four showcased a triple overtime game in which Philadelphia nearly doubled the shots Toronto took. On the 75th shot for the Flyers, at 13:54 of the third overtime Mark Recchi scored his second goal of the game to help the Flyers take a 3–2 win.[20] Sami Kapanen scored two power play goals in game five to assist the Flyers in a 4–1 win and took a 3–2 series lead.[21] In game six, Ed Belfour helped Toronto force a seventh game with 35 saves in a double overtime 2–1 victory.[22] The Flyers routed the Maple Leafs in game seven 6–1 with Mark Recchi scoring two goals and an assist and Justin Williams and Claude Lapointe both scoring a goal and two assists.[23]

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Round 1 and even Round 2 2004 Playoffs

2004 Round 1 and yes Round 2

Contrary to modern Leafs’ fan expectations, the Stanley Cup series actually has more than one round. Leafs beat Ottawa 4 games to 3 in Round 1, only to lose in Round 2 to Phillie 4-2. This, as unimaginable as this could be, was the last time Leafs won one, as in ONE, round of the playoffs.

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The Leafs Playoffs 2014-2015-2016

Mercifully there were no round one flame outs in these years, as it is prerequisite that the team actually makes the playoffs. These seasons did, however, allow for the drafting of Mitch Marner and Auston Matthews.

That would make the Leafs a playoff team once out of the past 11 years. Hard to imagine.

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2017 Round 1 Washington

2017 Round 1 Washington

The Washington Capitals earned the Presidents’ Trophy for the second consecutive year as the NHL’s best regular season team this time with 118 points. The Toronto Maple Leafs finished much further down the list, squeaking into the playoffs with 95 points as the second wild and last wild car. No one gave the Leafs much of a hope.

The series became only the third playoff series in NHL history in which five games were decided in overtime.

In game 1, Toronto had a two-goal lead in the first ten minutes of the first game. Washington went on to tie the game and won 3–2 in overtime from Tom Wilson‘s goal.

In game 2, rookie Kasperi Kapanen scored twice including the game-winner in double-overtime leading the Maple Leafs to a 4–3 victory.

Washington took two two-goal leads in game three; the first pick in the 2016 NHL Draft, Auston Matthews, helped soften the lead with his first playoff goal, but after the Capitals got a 3–1 lead, the Maple Leafs scored twice to tie the game. Then in overtime, Tyler Bozak tipped a shot past the Capitals’ goaltender to give the Leafs a 2–1 series lead.

Game four was the only game of the series not to go into overtime; Tom Wilson and T. J. Oshie both scored two goals and Oshie’s second goal proved to be the game-winner in a 5–4 victory after an attempted comeback by Toronto was thwarted.

Game five featured the fourth overtime game of this series with Justin Williams scoring for Capitals in a 2–1, taking a 3–2 series lead in the process.

In game six, the game went to overtime for the fifth time this series and at 6:31 of the first overtime period Marcus Johansson scored his second goal for the Capitals in a 2–1 victory and another trip to the second round.