via OHL Images

via OHL Images

Three Sault Ste. Marie Greyhounds were selected to the National Hockey League on June 30. Darnell Nurse went 7th overall to the Edmonton Oilers. Tyler Ganly went to the Carolina Hurricanes in the sixth round, and with the penultimate pick of the draft, the Boston Bruins took Mitch Dempsey at No. 210.

A fourth Greyhound, Sergey Tolchinsky, went undrafted. Listed at 5’9″ and 160 lbs, the young Russian’s weaknesses lay in some of hockey’s most up-for-debate attributes: size, physical play, and grit. He had been ranked 67th on TSN analyst Craig Button’s rankings, and 56th on Hockey Prospectus’ Corey Pronman’s list.

Depending on who you asked, he’d been projected as going anywhere between the second and fifth rounds. All it takes is one team to take a risk on a talented young player like Tolchinsky. In his rookie season in the Ontario Hockey League, Tolchinsky scored 26 goals and was the third-leading point-getter among rookies behind Sarnia’s Nikolay Goldobin and Erie Otter phenom Connor McDavid.

Tolchinsky didn’t sit down through all 211 picks. By the fourth round, he was notably antsy, pacing up and down the stairwells and by the seventh round, stood in the aisles next to the concession stands as the Prudential Center emptied out. He was dejected. His entire family had come out from Russia to be a part of the first step towards an NHL career, but the hours dragged on and nobody announced his name.

“There’s nothing you can say at that point to ease the disappointment,” Greyhounds general manager Kyle Dubas said via email. “Sergey’s friends and family began milling about, everyone unsure of what to do or say at that point.”

By then, a scout from the New York Rangers met up with Tolchinsky’s agents, Mark Gandler and Todd Diamond, and before the end of the draft, the two parties had an agreement that Tolchinsky would attend the team’s prospect orientation camp that week. On the bus back to the hotel, Tolchinsky received another invite to attend an orientation camp, this time from the Carolina Hurricanes in mid-July. Two months later, the Hurricanes committed. They pretty much had to. The Internet buzzed about Tolchinsky’s performance at the ‘Canes camp and local beat reporters raved.

In committing to the young forward, the Hurricanes exposed themselves Thursday to a chance at benefitting from an inefficiency in hockey’s antiquated scouting system. It took a lot to get Tolchinsky to where he was, but first he had to ignore his original agent’s advice.

The Canadian Hockey League circuit is difficult to understand for casual fans. It’s split up into the Western, Ontario, and Quebec Major Junior Hockey Leagues. Tolchinsky’s Greyhounds, in the OHL, are far up north, a long drive away from their nearest division rivals. It’s not uncommon for a big-name player to hold out and avoid committing to the organization that drafted them in an attempt to be traded to another team. First-round picks at the most recent NHL draft Nathan MacKinnon and Max Domi did exactly that, moving from Baie-Comeau to Halifax and Kingston to London respectively. Teams draft choices aren’t limited to Canadian players; big-market CHL clubs such as Portland, London and Kitchener are the ones that have the best shot at wooing American talent away from their NCAA commitments.

Tolchinsky didn’t come to the Greyhounds by either of those means. Each year a team gets two Import Draft choices and get to select European talent. As with American players, the European-born players have their own junior leagues at home to develop and catch the eye of major junior scouts. The import players that are most likely to join the CHL clubs that select them are the ones that need more exposure if they’re determined to make the NHL.

With the 12th overall pick in 2012, the Greyhounds took at risk by selecting Tolchinsky, who had an incredible U-17 World Championship run in Windsor. The problem for Dubas and the Greyhounds was that Tolchinsky’s then-agent Igor Larionov, who is based out of Detroit, didn’t want to see his client in remote place like Sault Ste. Marie. Windsor, home of the OHL’s Spitfires, is much closer, and a hotbed of junior hockey. Knowing that at the very least they could trade Tolchinsky’s draft rights for valuable assets, the Greyhounds selected Tolchinsky with their pick even without Tolchinsky’s stated commitment to the club.

Sometime in July, Tolchinsky fired Larionov and sought the services of Gandler, whom Dubas suggested was “a little more open” to geography. Late in the month, the Greyhounds got a call from one of Tolchinsky’s trainers asking why they hadn’t made an attempt to bring the future star over. “It seemed like a prank, but we followed it up,” admitted Dubas, who found out that Tolchinsky had assumed the Greyhounds selected him just to trade his rights, and he wanted to find out if the trade had been completed. “Once we told him, through the trainer, that our absolute preference was for him to play with the Greyhounds, it rolled very smoothly.”

Had Tolchinsky sat the 2013 season out, he’d have had difficulty obtaining a visa for this season. The foreign service workers strike in Canada has had an effect on Russian hockey players looking for permits to play for their Canadian Hockey League clubs. 2014 first round hopeful Ivan Barbashev, who spent last year with the Moncton Wildcats, is still stuck at home as the visas are being processed at a slower pace than usual. Tolchinsky was able to join the Greyhounds in 2012 after a brief visa delay, but he missed training camp. Had he not come over last season and skipped both camps, his chances of finding an NHL club willing to take him on would be even slimmer.

(The Greyhounds aren’t the only team acting aggressively with imported prospects. The Erie Otters and manager Sherry Bassin have gambled twice in consecutive years on imported players coming over: Oscar Dansk last year and Andre Burakovsky this past draft. Dansk was drafted 31st overall by Columbus at the 2011 NHL Draft, while Burakovsky was the 23rd overall pick with Washington. With so much media surrounding prospects, it’s become easier for teams to isolate which players have designs on coming to North America and committing to junior hockey programs, and the risks have paid off beautifully for Erie, who should be considered playoff contenders in the Western Conference after winning just 29 games in the past two seasons combined.)

Tolchinsky and Burakovsky have different reasons for taking a while to commit to their junior organizations. Burakovsky’s agent was quite adamant about Burakovsky’s status with the Otters, but he was in a hole because he’d admitted that he was going to the CHL before the Import Draft even took place. The Capitals have the option of sending Burakovsky to minor league Hershey or to Erie, but the Otters can’t even trade his rights since the CHL now forbids teams from trading import players within a year of their draft selection. The lack of choice a young prospect has is an unfortunate reality of junior hockey, but sometimes it can be a blessing. While Tolchinsky stood in tears and undrafted back in June, it probably didn’t occur to him that at that point, he was open to the services of all 30 teams. A good camp with New York or Carolina, and one of them would surely offer him a deal so that nobody else could.

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In his book The Black Swan, author Nassim Taleb divides the universe into two separate conceptual countries called Mediocristan and Extremistan. In Mediocristan, if you sit 200 people in a room and add the heaviest man in the world, he would represent a small percentage of the total weight of the 201 people. Much of the world takes place in Extremistan, where one outlier can change the balance of the entire group. Take the same 200 people and add in Bill Gates. He has close to the entire share of wealth of the 201 combined people in the room.

Unpredictable events shape our world. The way the Internet is used today was inconceivable 20 years ago. Check out 2001: A Space Odyssey for all you need to know on how people envisioned our future, and you can easily go back as recently as Futurama, where Matt Groening’s vision of the year 3000 contains elements that are already obsolete in 2013 such as bulky cellphones, CDs, or, for Canadian readers, the one cent coin. Some Black Swans are positive, and some, like stock market crashes, are negative. From the book’s final chapter:

In the end this is a trivial decision making rule: I am very aggressive when I can gain exposure to positive Black Swans—when a failure would be of small moment—and very conservative when I am under threat from a negative Black Swan. I am very aggressive when an error in a model can benefit me, and paranoid when the error can hurt. This may not be too interesting except that it is exactly what other people do not do. In finance, for instance, people use flimsy theories to manage their risks and put wild ideas under “rational” security.

For a day in August, there were some real interesting moves on Thursday. The one that has the potential to yield the most returns isn’t the one that involves statistical darlings Mikhail Grabovski or Chris Tanev, nor is the most interesting one Montreal’s signing of Douglas Murray, a slow, but tough, defenceman that personifies one of hockey’s market inefficiencies. It was Tolchinsky, because his endless upside comes with zero cost.

The Draft takes place in Extremistan. Outside of the top 20 picks, who makes the NHL? Prospects that aren’t drafted high need 100 of 100 things to go exactly right for them to have a chance at playing big minutes in the show. People often talk about the Detroit Red Wings finding late round gems in Pavel Datsyuk and Henrik Zetterberg, but nobody mentions Todd Jackson, Ken Davis, Anton Borodkin, Petja Pietilainen, David Petrasek, Greg Willers, Evgeny Afanasiev, or any of the dozens of Detroit Red Wings late round draft picks that never sniffed the NHL, let alone greatness. Datsyuk and Zetterberg are Black Swans, their success contributing greatly to our perception of the Wings’ scouting staff despite them exceeding the most optimistic projections of the staff at the time—both Datsyuk have become superstars and maybe even Hall of Fame players.

When you look at depth players in the NHL, it’s curious to note that even the fourth line checking centremen were once superstars in junior hockey. Manny Malhotra scored 51 points in 57 games with the Guelph Storm in his draft year and made the NHL as an 18-year-old after being taken 7th overall by the Rangers. Dave Bolland scored 130 points in his final junior season with the London Knights, two seasons after being taken 32nd overall by the Chicago Blackhawks. Andrew Cogliano scored 102 points in 49 games with the St. Michael’s Buzzers of the Ontario Junior A league before getting picked 25th overall by Edmonton.

Hockey players, especially forwards, bear a common thread: the successful ones score a lot (except in the case of Colton Orr and Matt Kassian) and the ones that don’t score get weeded out at the lower levels. All the Hurricanes are doing when they’re signing Tolchinsky to a contract is adding one contract to the 50-contract limit. The lower bound is defined, as in Tolchinsky doesn’t play a game in his career, and the upper bound is not. The Hurricanes have put themselves in position to benefit greatly if those 100 of 100 things go exactly right, and it didn’t cost them anything, exactly how Taleb describes it in the quoted section above.

Brian Burke began looking at college free agents as a way of shoring up his prospect cupboard. He cast several nets and wound up with one NHLer in Tyler Bozak, which is better than zero NHLers by not casting those nets. Rarely does a situation come about like Tolchinsky’s where a high-scoring junior prospect goes undrafted and then handed a contract during the summer. If you look back at rookie scorers in the OHL, you don’t come across one in the top five that went undrafted since Vladimir Nikiforov in 2005-2006, who was a productive minor pro player for years before shipping himself to the KHL last year. Some of those rookies have become stars. Some haven’t. That’s hockey, but the point is that they all had a chance of being something greater than their OHL numbers, and not a single team it appeared on June 30 was willing to give Tolchinsky a chance.

Tolchinsky picked himself up by the bootstraps and made an impression at prospect camps for both the Rangers and the Hurricanes, his skillset was too tempting to resist. The Hurricanes offered him a contract, and Tolchinsky signed it. For Dubas, he called it one of the best moments in his career: ”To see Sergey, who had his entire family in Newark from Russia have to sit through all seven rounds and not hear his name, and dust himself off the next before going on to earn an NHL contract a month later, was the best.”