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Historians debate the date, but most peg the New York Islanders rebuild beginning at the 2008 draft. A huge part of Garth Snow's new direction was to compile and hang on to draft picks, beginning with that draft and the decision to trade down twice in the first round.
The product of those trades is a somewhat blurry lineage, as the keystone has played 211 NHL games but also saw AHL time this year, while the other picks were used for multiple selections and trades over multiple years.
Suffice to say, extra picks don't necessarily land you a key player; rather they give you flexibility for trades and a shotgun approach to drafting (more bullets in the chamber), each of which increases your odds of landing a key player.
Of course, that doesn't work if you don't draft well and don't trade well. Have the Islanders done so? Four summers is too soon to tell on 18- to 21-year-olds, but it's still a fun exercise to look back at what was on the table when the Islanders' turn came up.
I was going to do this only with the Islanders' 2011 draft to understand the choices they had before them at each pick, but the speculation got too wild for my tastes. So instead I'm looking back at the whole rebuild, in a way similar to but not quite inspired by a recent Copper & Blue post.
For "they coulda got THAT guy!" examples, at the top of the draft I limited it to a few choices after the Islanders picked. I figure if three teams pass on a kid, that's enough to stop pretending the "right" choice was obvious to all. Later on, I expanded that to anyone with NHL experience or, barring that, a funny name.
Just a warning before we dig in: You're going to recognize the Islanders' late-round picks more simply because we think about them more. But overall, the rules is that very few of these guys have appeared in NHL games yet, and many never will.
2008
| 2008 | Pos | Player | Could have had... |
| 1 (9) | C | Josh Bailey* | Cody Hodgson (10) or Tyler Meyers (12) |
| 2 (36) | C | Corey Trivino | Uhh...Roman Josi (hey, he's Swiss) |
| 2 (40) | d | Aaron Ness* | Yann Sauve (41), Luke Adam (44) |
| 2 (53) | d | Travis Hamonic | Patrice Cormier (54) |
| 3 (66) | d | David Toews*** | Marc-Andre Bourdon (67) |
| 3 (72) | d | Jyri Niemi*, *** | Kirill Petrov (73) |
| 3 (73) | R | Kirill Petrov** | Evgeny Grachev (75) |
| 4 (96) | d | Matt Donovan | Jamie Arniel (97) |
| 4 (102) | C | David Ullstrom | Johan Motin (103) |
| 5 (126) | g | Kevin Poulin | Matt Calvert (127) |
| 5 (148) | L | Matt Martin | Philip Larsen (149) |
| 6 (156) | d | Jared Spurgeon *** | Teemu Hartikainen (163) |
| 6 (175) | C | Justin Dibenedetto **** | Tommy Wingels (177) |
* Technically, this choice is more complex thanks to the trade down. The Islanders could have had Luke Schenn or Nikita Filatov (lol) if they hadn't traded down at all, and Colin Wilson if they hadn't traded down twice. Those trades got them the picks that netted Aaron Ness, Jyri Niemi, and David Ullstrom.
** The route to the Kirill Petrov pick is insane, and one of those reasons I thank Bossy for ProSportsTransactions.com. The Denis Grebeshkov trade (February 2007) netted Marc-Andre Bergeron and this Petrov pick. But this Petrov pick was sent back to the Oilers in July 2007 for the pick that netted Travis Hamonic. Meanwhile, the Petrov pick (along with the Tyler Meyers pick) went to Anaheim as compensation for the Dustin Penner signing. The Ducks of course flipped the one pick to Buffalo, and the Petrov pick to the Islanders for ... Marc-Andre Bergeron.
*** Toews and Spurgeon's rights were allowed to lapse. Niemi was traded to the Rangers for one of the picks that got the Islanders the pick that netted Brendan Kichton in 2011. (Still with me?)
**** DiBendetto's pick was acquired in the 2007 trade of Chris Simon to the Wild.
Wow, that's a lot of italics. Sorry.
There's a reason people look at 2008 as a pivotal draft, and it's not just because of the timing. From top to bottom there remains a lot of realistic potential there. The fact that two of the three players no longer with the organization are sandwiched in the middle of the 3rd round really underlines how it's a crapshoot where having multiple picks isn't a bad idea at all.
2009
| 2009 | Pos | Player | Could have had... |
| 1 (1) | C | John Tavares | Victor Hedman (2), Matt Duchene (3) |
| 1 (12) | d | Calvin de Haan* | Zack Kassian (13), Dmitry Kulikov (14) |
| 2 (31) | g | Mikko Koskinen | Landon Ferraro (32), Ryan O'Reilly (33) |
| 3 (62) | g | Anders Nilsson | Ben Hanowski (63) |
| 4 (92) | C | Casey Cizikas | Alex Hutchings (93) |
| 5 (122) | d | Anton Klementyev | Olivier Roy (133) |
| 6 (152) | C | Anders Lee | Dave Labrecque (153) |
* The Islanders famously did a reverse-Bailey and traded up twice for de Haan. The first one gave the Blue Jackets the pick that became Kyle Palmieri. The second one gave the Wild the pick that became Nick Leddy. The Islanders also gave up picks that would become Anders Nilsson and Casey Cizikas in these maneuvers, but they got both of those picks back when the Blue Jackets wanted to trade up for Kevin Lynch.
Much lighter draft, but still several promising picks top to bottom, even without Tavares. While taking two goalies before 62 was a risk (one arguably mandated by Rick DiPietro's injury saga), interestingly the most make-or-break decision remains what kind of player de Haan becomes.
2010
| 2010 | Pos | Player | Could have had... |
| 1 (5) | W | Nino Niederreiter | Jeff Skinner (7), Alexander Burmistrov (8) |
| 1 (30) | C | Brock Nelson* | Tyler Pitlick (31), Jared Knight (32) |
| 3 (65) | L | Kirill Kabanov | Radko Gudas (66) |
| 3 (82) | L | Jason Clark | Matt MacKenzie (83) |
| 5 (125) | d | Tony Dehart | Freddie Hamilton (129) |
| 7 (185) | g | Cody Rosen | None. There is none more Rosen. |
* The Islanders traded the #35 (Ludvig Rensfeldt) and #58 (acquired for Andy Sutton) to grab Nelson.
What an interesting year: Nino may prove to be a reach or may prove to be brilliant, but he should be solid regardless. Nelson was possibly worth swapping two picks IF you believe he wouldn't be there at #35, which is plausible. Kabanov may yet prove to be the steal of the draft, a risk the Islanders could take by virtue of having numerous picks in this era.
And then you have Dehart who is already gone, and Rosen who was a head-scratcher (he didn't believe it when he got the call) but well we're all pulling for him anyway. Clark has clear talent but required two hip surgeries this summer.
2011
(Note: Sorry, I left out Brenden Kichton originally. Thank you to the eagle-eyes who caught it.)
| 2011 | Pos | Player | Could have had... |
| 1 (5) | C | Ryan Strome | Mika Zibanejad (6), Sean Couturier (8) |
| 2 (34) | d | Scott Mayfield | Tomas Jurco (35) |
| 2 (50) | C | Johan Sundstrom* | Alexander Ruuttu (51) |
| 3 (63) | d | Andrey Pedan** | Vincent Trocheck (64) |
| 4 (94) | d | Robbie Russo | Jean-Gabriel Pageau (96) |
| 5 (125) | L | John Persson | Fredrik Claesson (126) |
| 5 (127) | d | Brenden Kichton |
Seth Ambroz (127) |
| 7 (185) | C | Mitchell Theoret | Jordan Fransoo (186) |
* The Sundstrom pick was acquired along with a 2012 5th in the James Wisniewski trade.
** The Islanders acquired the Pedan pick (63) the previous summer from the Avalanche in exchange for the 2010 4th (95), which the Avs used to select Stephan Silas.
So obviously it's too early to make anything sensible of the most recent draft. For what it's worth, it was rated well by NHL observers, and two of the pleasing picks were made possible by trades.
Pre-Rebuild
How did this rebuild come about? Well, in a weird way Ryan Smyth helped pave the way. Snow did what I suspect a lot would do in their first year as GM: He went for it, dumping some prospects they didn't want and a first-rounder for a rental who, despite much wooing, would not re-sign. That season Snow also swapped a 2nd for renting Richard Zednik. Snow has yet to spend his picks so freely again.
| 2007 | Pos | Player | Could have had... |
| 3 (62) | d | Mark Katic | Maxime Macenauer (63) |
| 3 (76) | L | Jason Gregoire | Nick Palmieri (79) |
| 4 (106) | L | Maxim Gratchev | Mitch Fadden (107) |
| 6 (166) | d | Blake Kessell | Johan Harju (167) |
| 7 (196) | d | Simon Lacroix | Michael Ward (197) |
The year of the Smyth trade and going for it. Not a lot of picks in the draft, and the best one might have been the guy who used an NCAA/CBA route to become a free agent this summer and sign with his hometown team.
It's not that the Islanders chose poorly here, it's that they left themselves with few choices in what may prove to be an unimpressive draft year anyway. (Edmonton used the Smyth pick in the first round on Alex Plante, whose credentials are far from certain.)
Pre-Snow: The Weird Summer
| 2006 | Pos | Player | Could have had... |
| 1 (7) | R | Kyle Okposo | Peter Mueller (8), James Sheppard (9) |
| 2 (60) | L | Jesse Joensuu | Jamie McBain (63) |
| 3 (70) | W | Robin Figren | Brad Marchand (71), Cal Clusterbuck (72) |
| 4 (100) | R | Rhett Rakhshani | Joonas Lehtivuori (101) |
| 4 (108) | G | Jase Weslosky | Matt Beleskey (112) |
| 4 (115) | C | Tomas Marcinko | Hugo Carpentier (118) |
| 4 (119) | C | Doug Rogers | Bboby Hughes (123) |
| 5 (126) | d | Shane Sims | Andrew Bodnarchuk (128) |
| 5 (141) | W | Kim Johansson | Olivier Magnan (148) |
| 6 (160) | d | Andrew MacDonald | Viktor Stalberg (161) |
| 6 (171) | R | Brian Day | Petteri Wirtanen (172) |
| 6 (173) | g | Stefan Ridderwall | Michael Dupont (175) |
| 7 (190) | L | Troy Mattila | Benn Ferriero (196) |
So this is the yang to 2008's yin. People will debate forever who was in charge -- this was the summer of Neil Smith's 40 Days -- and whose crew decided what at the draft, but it obviously wasn't Snow, who would still be the club's veteran goalie for one more month.
For the present I'm just interested in how many "bullets" they had and how few have hit. Okposo is a success and better than the first-round picks that immediately followed him. Andrew MacDonald is one of those true late-round late bloomers. Rakhshani may yet show something at the NHL level. The rest...? Sometimes having a lot of shots isn't enough. As far as obvious regrets though, only the Figren pick stands out for who followed him.
Again, it's too early to tell and we're prone to lodge more hope in the prospects we know than in the prospects other teams' fans know. But so far in the rebuild years, the Islanders don't have many (if any) clear "Awww, they shoulda drafted THAT guy!" moments. If anything, it's the pick swaps that will keep us guessing, although those too usually created other options that complicate the question.
This is an early look. We'll look back again in a year or two when The Other Kessel is just a brother and ... maybe the Natural Born Kirills are embodying Russians with love?