how many of the last 10 cup teams owed their success (both the playoffs/finals and the road there) wholly to players drafted and developed within their system, and how many top 5 picks to they have?
It's much more complicated than that. How many prospects that the team drafted and then traded for have made an impact? different GMs also have different visions. Based off your criteria, let me see what I can find.
2014 -
LA Kings - Anze Kopitar (11th overall), Drew Doughty (2nd overall), Dustin Brown (13th overall), Tyler Toffoli (47th overall), Jake Muzzin (unsigned/undrafted), Tanner Pearson (30th overall), Dwight King (109th overall), Alec Martinez (95th overall), Slava Voynov (32nd overall), Kyle Clifford (35th overall), Trevor Lewis (17th overall), Jonathan Quick (72nd overall).
So, (1) top 5 pick. They had others that they traded. As well, many of these picks were within years of each other. They ended up with 12 guys they drafted...
2013 -
Chicago Blackhawks - Patrick Kane (1st overall), Bryan Bickell (41st overall), Jonathan Toews (3rd overall), Duncan Keith (54th overall), Andrew Shaw (139th overall), Dave Bolland (32nd overall), Brandon Saad (43rd overall), Niklas Hjalmarsson (108th overall), Marcus Kruger (149th overall), Brent Seabrook (14th overall), Ben Smith (169th overall), Brandon Bolling (undrafted), Corey Crawford (52nd overall)
So, Chicago had (2) top 5 picks on their team. Lots of role players. 13 players they drafted.
2012 -
Los Angeles Kings - See 2014. They also had Jordon Nolan (186th overall), Andrei Loktionov (123rd overall). 12? again
2011 -
Boston Bruins - Daniel Krejci (63rd overall), Patrice Bergeron (45th overall), Brad Marchand (71st overall), Milan Lucic (50th overall), Tyler Seguin (2nd overall), Tim Thomas (undrafted)
(1) top 2 pick. They had others but none stuck on the team. This team most resembles the Wild in terms of how many players they drafted vs free agents. 6 guys they drafted.
2010 -
Chicago Blackhawks - See 2013. They also had Dustin Byfuglin (245th overall), Troy Brouwer (214th overall), Adam Burish (262nd overall), Jordan Hendry (undrafted). Again around 13ish.
2009 -
Pittsburgh Penguins - Evengi Malkin (2nd overall), Sidney Crosby (1st overall), Maxime Talbot (234th overall), Kris Letang (62nd overall), Tyler Kennedy (99th overall), Jordan Staal (2nd overall), Rob Scuderi (134th overall), Brooks Orpik (18th overall), Alex Goligoski (61st overall) (also Satan won a Stanley Cup that year!)
So, this is the team everyone thinks you need a bunch of top 5 picks for since they had 3. 9 guys they drafted.
2008 -
Red Wings - Pavel Datsyuk (171st overall), Henrik Zetterberg (210th overall), Nicklas Lidstrom (53rd overall), Jiri Hudler (58th overall).Tomas Holmstrom (257th overall), Johan Franzen (97th overall), Valtteri Filppula (95th overall), Niklas Kronwall (29th overall), Brett Lebda (undrafted), Tomas Kopecky (38th overall), Matt Ellis (undrafted), Dallas Drake (116th overall), Derek Meech (229th overall), Mattias Ritola (103rd overall), Darren McCarty (46th overall), Jonathan Ericsson (291st overall), Kyle Quincey (132nd overall), Darren Helm (132nd overall), Chris Osgood (54th overall)
No one in the top 5 picks. 19 guys they drafted.
2007 -
Anaheim Ducks - Shane O'Brien (250th overall), Corey Perry (28th overall), Chris Kunitz (undrafted), Dustin Penner (undrafted), Drew Miller (186th overall), Stanislav Chistov (5th overall), Ryan Shannon (undrafted), Ryan Getzlaf (19th overall), Andy MacDonald (undrafted), Tim Brent (75th overall), Ryan Carter (undrafted)
(1) top 5 pick LOL and he sucked. Lots of undrafted guys. Strangely enough, no top 4 drafted defensemen. 11 guys they signed, drafted.
2006 -
Carolina Hurricanes - Eric Staal (2nd overall), Erik Cole (71st overall), Craig Adams (223nd overall...and drafted by the Whalers!), Chad LaRose (undrafted), Andrew Ladd (4th overall), Josef Vasicek (91st overall), Niklas Nordgren (195th overall), Michael Zigomanis (46th overall), David Gove (undrafted), Keith Aucoin (undrafted), Niclas Wallin (97th overall), Danny Richmond (31st overall), Cam Ward (25th overall)
So, (2) top two guys. 13 of their guys.
So, we have some extremes (Boston, Detroit) but around 10-13 guys drafted seem to end up on the team and playing some role for their organization in the playoffs.
Just for comparison sake:
Mikael Granlund, Justin Fontaine, Erik Haula, Mikko Koivu, Jason Zucker, Jonas Brodin, Matt Dumba, Christian Folin, Nate Prosser, Marco Scandella, Jared Spurgeon and Darcy Kuemper for the Wild.
So about average.
I will say Minnesota has better defense but most of the teams drafted better offense than Minnesota - which fits their MO.