What it took to get Orr on NHL ice on this date in history.

Bobby Orr is one of the best defensemen to ever play the game of Ice Hockey in a professional capacity. Ever. Period. That is a lofty title that only one other Bruin could conceive of breaking into the conversation with, let alone any other player in the NHL. And he was not just another cut and dry signing from the farm leagues. His signing was a multi-year saga of intrigue, agents fighting on his behalf, parents demanding to keep their boy in Ontario, owner stubbornness, and a revolutionizing of how players enter the NHL.

Let's go through that winding history to see just what it took to get Bobby Orr to wear number four.

1961-1962: Bobby gets the family a new car.

'61 was the year Bobby Orr was officially scouted by Wren Blair. Boston was rebuilding. More than you think they would be today. They had just finished up a 15-42-13 season. In this time, they played 70 games in a season. This is what you would call a "Catastrophically bad" year.

They needed somebody. And Blair was convinced this was going to be that guy.

Blair referred to him as a cross between Doug Harvey and Eddie Shore. This was the kind of praise you didn't often hear for players. And still don't today. Boston quickly put money and resources towards making sure Orr was committed to being a Bruin. They funded his team, and made frequent visits to his house.

In the following year, the Bruins were convinced by Blair to help buy another franchise that had gone dormant for a few years. The B's already had one in the region, but Blair was convinced that they could do something with this. The Bruins relented, and took over almost half of the ownership of the team on Blair's behalf and the Oshawa Generals were founded. Just one condition.

Bobby Orr, no matter what, has to be an Oshawa General.

Bobby Orr was around 13 at the time. And he had to convince the Orr family to sign him. To Blair's delight, he was able to convince the Orr's to let him try out for the team the Bruins already ran in juniors: The Niagara Falls Flyers. Everything was going fine until Bruins owner Weston Adams had a meeting with the boy, and sent him on his way home: thinking he was too young to be worth all this money and time. Blair smoothed out the situation, and got a commitment signing from the Orr's for Bobby to sign with Boston at age 18.

Of course, that wasn't everything. He signed an agreement with terms.

Here is some of the highlights:

• Bobby was to stay in Parry Sound for School. Parry Sound, for those of you unaware, is two and a half hours north of Oshawa, where he plays junior.
• Orr will miss practice for the above, and only be available to play on the weekends.
• $10,000 CAD signing bonus (which is almost 80,000 CAD today)
• One new car for the Orrs.
• The Bruins will pay to stucco the Family home.

I don't know about you but personally the idea of stucco'ing one's house and making an NHL team pay for it somehow sounds way weirder than paying the equivalent of 80 grand for a teenager that might be as good as advertised.

1965: Bobby wants to play hockey so badly he gets a guy fired.

In these times, the OHL and similar junior teams were almost entirely a farm system for the NHL. The easiest path one could take. He was picked up by Boston and sent to the fledgling Generals, who survived a merger that got them placed in the OHL. And in true Orr fashion, he was scoring at his usual incredible pace in Oshawa, who had won the OHL Championship and was on their way to the Memorial Cup, in no small part due to his incredible scoring and assisting: getting 94 points.

Then he suffered a groin injury.

He wanted to play it out. So did a lot of other people, including his family (who were no doubt stoked to know that an NHL team wanted him), his team (which had recently been accepted back into the OHA) , and Maple Leaf Gardens, who had advertised the championship game as the young phenom's final junior game.

The Bruins on the other hand, wanted absolutely zero part of him being in a game while he was hurt. They had stucco'd a wall for this kid, damnit. And they didn't want this guy to show up to camp even more hurt than he already was. He, his family (and the team the Bruins owned) objected. The team wanted to sell tickets, The Orrs wanted to be part of a national championship. They even made a big proclamation:

If he didn't play, He would never play in a Boston Bruins uniform. Ever. After all, he wasn't signed to the team officially. He was just committed to their prospect system. He could sign with anyone he wanted, technically.

Wren Blair, who was involved in the Gen's management structure now, decided that he would take the fall for the team's best (and arguably most important) player. Orr played. He wasn't that big of a factor in the game, and Oshawa lost to Edmonton. Wren Blair would leave the organization as expansion started and worked for Minnesota. Oshawa's coach in the meantime, was fired for letting this happen.

1966: Bobby Orr gets PAID.

Now we need to take a quick minute to talk about an NHLPA founding father: Art Eagleson.

Eagleson is a milestone figure in hockey's history: an advocate for one of the greats, a creator of an organization designed to give the player's a say, and one of the champions of players even having agents in the first place.

He was also a crook who embezzled funds from international tournaments, stole loads of cash from and conned his clients (including Orr himself). He is controversial in the extreme.

He was also instrumental in getting Orr onto Boston's roster.

See, after the first meeting in Warren Adam's first meeting with Bobby, Doug Orr, his father, wasn't exactly a big fan of the way Boston treated his son. After all, they were pouring literally hours into recruiting his son. And they kept badgering him even after that whole mess was ironed out. So he ran into Eagleson in a softball game and asked to help him out with Orr's relationship with the league. He agreed to work for the family for free.

Eagleson and Bobby hit it off, and Eagleson was soon determined to get this young guy as much money has humanly possible. (Presumedly so he could steal it from him later)

When Hap Emms, the Bruins lame-duck GM who had presided over about 8 seasons of terrible hockey, offered a $7,000-$8,000 dollar contract for his first two years with a signing bonus of about $5,000, Eagleson threw down the gauntlet on Emms: $100,000 USD or Orr was going to be playing for Team Canada. Orr at this point desperately just wanted to play in the NHL, but Eagleson convinced him to follow along.

Now, you are Hap Emms, who has watched this kid from Ontario destroy the Metro-Junior-A and then the OHA in scoring from the position of defenseman. Which at this point does not have anybody being held up as an example of fine scoring threats. You have probably spent well over 30,000 dollars just trying to get this kid into your team that has otherwise been playing like dog shit for almost a decade now and have not been to the playoffs since the decade began. And this guy who isn't even his father or the kid himself has done the unprecedented and said "Here's what we want you to pay him. Or we make a legend of this guy on Team Canada."

And I must stress that this never happened up until this point in history. You, the GM, had all the power in the world. You might be tempted to throw Eagleson out of your office and forget about that kid.

...But then you remember that this kid has not stopped scoring. In fact, he's only getting better. He is already way too good for his station. If he leaves, he's not on Team Canada for a few weeks. He could be a Maple Leaf. Or a Blackhawk. Or a Ranger.

Or a Hab.

And then you think about all that money and time and effort and literal jobs being thrown out just to make sure this kid sells tickets. He's already a proven commodity in Ontario. He could easily be one in Boston. Maybe, just maybe...this guy is worth that kind of money.

Emms and Eagleson talk, and negotiate, and finally they agree to a figure. It is less than $100,000, and has a 25,000 dollar signing bonus attached.

In one fell swoop, Bobby Orr is now the highest paid player in league history (up to that point).

October 19th, 1966: Bobby Orr is a Boston Bruin.

Bobby Orr, who was offered Dit Clapper's number but turned it down for the number 4, dons his Bruins jersey for his official NHL debut against the Detroit Red Wings. He gets an assist on the winning goal.

Harry Sinden, who was coaching at the time, said this about him:

"Our fans had heard about this kid for a few years now. There was a lot of pressure on him, but he met all the expectations. He was a star from the moment they played the national anthem in the opening game of the season."

The rest of that 1966 season:

The Bruins don't make the playoffs, but Bobby Orr puts up an incredible 41 points in his first year as a rookie defenseman, won the Calder,  and was a finalist for the Norris Trophy. The winner that year, Harry Howell, ominously upon receiving it and thanking the academy that Orr "would own this trophy from now on." He also swelled the Boston Garden attendance numbers up by 40,000 fans. So he is sort of worth all that, the Bruins decide.

And the rest, they say, is history.

Was it worth it?:

Remember that the Bruins were a brutally bad team for about eight years prior to his signing. In a league with six teams that was about to have six more dropped on them. Remember that the Bruins after 1966-67 season would go on to make the playoffs in some fashion or another until almost the turn of the century.

And win the Stanley Cup twice in his all-too short NHL career.

And have one of the most iconic moments in sports history go to a Boston team.

I think it was worth every penny. All that blood, sweat, money and tears paid off big time.

So thank you to all those who made Bobby Orr's debut on this day 50 years ago a possibility for the Boston Bruins.

And of course, thank you to Mr. Bobby Orr, for being the greatest hockey player to wear Black and Gold.