The Flying Octopus

An all new Red Wings hockey podcast hosted by Tony Wolak, Devin Little and Evan Sabourin

Episodes

7 days ago

28 min

Summary
In this episode, Devin and Tony discuss the Detroit Red Wings' branding, jersey designs, and the ongoing search for a new general manager, providing insights into team culture and strategic decisions.
Keywords
Red Wings, Hockey Town, jersey design, GM search, Detroit sports, team branding, NHL, fan engagement
Key Topics:
Red Wings' jersey design and brandingThe significance of Hockey Town in Detroit cultureThe ongoing search for a new Red Wings general managerFan engagement and merchandise strategiesThe impact of team branding on fan loyalty
 sound bites
"Hockey Town is more than just a logo""Hockey Town adds to the Red Wings' lore""Minimal effort in jersey design diminishes appeal"
Chapters
00:00 Introduction and episode overview02:14 Devin's personal journey and return to writing03:42 Red Wings GM search updates and sources08:23 Sean Horkoff's role and recent trade activity12:32 Analysis of new player Sutter Mazzati13:40 Discussion on Red Wings' jersey and branding strategies16:53 The significance of Hockey Town in Detroit19:40 Historical perspective on Hockey Town branding24:04 Critique of the proposed Hockey Town remix jersey26:31 Jersey design as a marketing tool28:22 Closing remarks and future plans

7 days ago

28 min

Aug 13, 2026

47 min

Summary: 
In this episode former USA TODAY lead hockey writer and Hall of Famer, Kevin Allen,  shares insights on the Detroit Red Wings' current challenges, prospects, and future strategies. We explore team dynamics, management decisions, and the importance of analytics in shaping the franchise's path forward.
Keywords:
Red Wings, Kevin Allen, NHL, hockey analysis, team management, prospects, analytics, Detroit hockey
Key Topics:
Red Wings' management and organizational challengesThe impact of Dylan Larkin trade requestRole of analytics in team buildingProspects and player development strategiesTeam culture and organizational funkFuture outlook for Detroit Red Wings
Sound Bites
"Larkin is pretty valuable to the Red Wings""You gotta pay Edmondson more than Cider""Goals are essential for playoff success"
Chapters
00:00 Introduction and Guest Background03:00 Larkin's Value and Team Impact04:01 New GM Search and Management Style05:03 Potential Candidates and Analytics Approach06:20 Involvement of Jeff Greenberg and Analytics in Hockey08:13 Pressure on Illich and Franchise Expectations09:05 Drafting Challenges and Future Strategies10:28 Team Building and Youth Development12:13 Organizational Funk and Team Morale14:27 Defense and Offense Outlook16:46 Contract Negotiations and Player Relations18:38 Alex DeBrincat's Future and Contract Talks20:32 Prospects to Watch in 202622:17 Player Development and Prospect Management24:37 Team Environment and Player Morale27:51 Young Players and Future Impact31:00 Team Strategy and Draft Philosophy33:49 Defensive and Offensive Player Development39:38 Season Outlook and Optimism43:11 Closing Remarks and Final Thoughts

Aug 13, 2026

47 min

Jul 24, 2026

24 min

SUMMARY
In this episode, Tony Wolak and Devin L. explore the complexities of hiring a new general manager for the Detroit Red Wings, debating internal versus external candidates, and analyzing successful NHL organizational changes. They also touch on Patrick Kane's move to Chicago and its implications for the team.
KEYWORDS 
Red Wings, NHL, General Manager, Internal vs External Hire, NHL Organizational Change, Patrick Kane, Detroit Red Wings, Hockey Management, NHL Trades, Team Building
 key  topics
Red Wings GM search: internal vs external candidatesSuccess stories of NHL leadership changesImpact of Patrick Kane's move to ChicagoOrganizational change and team rebuilding strategiesThe importance of organizational knowledge in NHL management
SOUND BITES
"They are their own person and they're gonna make decisions on their own.""Change is change, don't just bring in a protege.""A clean slate feels like a fresh start."
CHAPTERS
00:00 Introduction to the Red Wings GM Search02:05 Devin's Wedding Plans and Personal Updates03:47 Discussion on Internal Candidates: Sean Horkoff and Others07:54 External Candidates and Successful NHL Examples11:58 The Value of Organizational Knowledge in Hiring16:08 Differences in Management Styles: Inside vs Outside Hires19:54 Case Studies: Vegas, Colorado, and St. Louis24:04 Addressing Team Rebuilding and Player Trades29:01 The Impact of Leadership Changes on Team Dynamics31:05 Patrick Kane's Move to Chicago and Its Significance31:56 Closing Remarks and Next Steps
Resources:
NHL Organizational Change Examples - https://www.nhl.com/news/nhl-organizational-changes-examplesPatrick Kane's Career Profile - https://www.nhl.com/player/patrick-kane/8470644Detroit Red Wings Official Website - https://www.nhl.com/redwingsVegas Golden Knights Management - https://www.nhl.com/news/vegas-golden-knights-managementSt. Louis Blues Management Transition - https://www.nhl.com/news/st-louis-blues-management
 guest links
Twitter - https://twitter.com/HockeywithDevinTwitter - https://twitter.com/FlyingOctopod
 

Jul 24, 2026

24 min

Jul 16, 2026

46 min

Summary:
In this episode, Evan, Tony, and Devin discuss the shocking news of Steve Yzerman stepping down as GM of the Detroit Red Wings, the team's future direction, and the implications for the franchise. They also touch on Patrick Kane's potential destinations and the broader NHL management trends.
Key Topics:
Steve Yzerman's tenure and departureRed Wings' team rebuild and management strategyThe NHL GM hiring process and analytics influencePatrick Kane's free agency and potential teamsImpacts of management changes on team performance
Sound Bites:
"Yzerman's tenure can be viewed differently now""The Red Wings are in a pivotal moment""This is the most hectic Red Wings summer in years"
Chapters
00:00 Intro and Wake-up Call08:11:48 Reactions to Yzerman stepping down
 
 Guest links
Twitter - https://twitter.com/HockeywithDevin
 

Jul 16, 2026

46 min

Jul 10, 2026

32 min

Summary:
In this episode, Tony Wolak and Devin Little delve into the recent NHL salary cap shifts, the record-breaking Leo Carlsson contract, and the ongoing Dylan Larkin trade saga. They explore how these developments are reshaping team strategies, player valuations, and the league's financial landscape.
Keywords:
NHL salary cap, Leo Carlsson contract, Dylan Larkin trade, NHL free agency, hockey contracts, NHL salary trends, Red Wings, NHL negotiations
Key Topics:
NHL salary cap increase and its impactLeo Carlsson's $18 million contract and its significanceThe Dylan Larkin trade saga and trade restrictionsFuture contract trends and free agency strategiesTeam building in the context of rising salaries
 
Sound Bites:
"Content dictates the format, don't force structure.""Leo Carlsson's contract shifts the NHL market.""You can't do that to Larkin out of respect."
Chapters:
00:00 Introduction and episode overview02:23 Leo Carlsson's record-breaking contract and its implications04:23 The significance of the $18 million deal for Carlsson06:28 Impact of Carlsson's contract on future negotiations09:08 The future of Alex DeBrincat and team building11:28 Historical context of NHL salaries and cap growth14:22 Red Wings' player contracts and market value16:43 The value of Larkin's contract and trade market19:36 Trade restrictions and potential trade scenarios22:36 The emotional and strategic impact of the Larkin saga24:51 Potential trade structures and third-team involvement27:10 The complexity of trade negotiations and team interests28:30 Training camp scenarios and leadership considerations29:02 Respect and team dynamics regarding Larkin's captaincy30:06 Humorous take on hockey drama as reality TV30:48 Potential media and entertainment angles on the saga31:00 Uncertainty around Patrick Kane and team roster moves32:12 Team building and offseason strategy post-Larkin33:06 Expected additional signings and team depth34:00 Summary and closing thoughts on NHL offseason trends
Resources:
NHL Salary Cap History - https://www.nhl.com/news/nhl-salary-cap-historyLeo Carlsson's Contract Details - https://www.espn.com/nhl/story/_/id/38012345/leo-carlson-18-million-per-year-contractDylan Larkin Trade Saga - https://www.freep.com/story/sports/nhl/red-wings/2023/07/15/dylan-larkin-trade-possibilities/
Guest Links:
Twitter - https://twitter.com/HockeywithDevin
 

Jul 10, 2026

32 min

Jul 3, 2026

42 min

In this week’s episode of The Flying Octopus Podcast, the fellas dive into Detroit’s July 1 acquisitions and what they mean for the organization. Viktor Arvidsson and Keegan Kolesar, in particular, address key offseason objectives, and the guys will share how. The discussion then pivots to the 2026 NHL Draft, where Evan got an up close view of Detroit’s draft picks as a credentialed member of the media. The guys recap Detroit’s selections, their value, and how the Red Wings adjusted their draft strategy away from the tried and true. The episode ends with a shout out for former guest Shane Malloy, who was hired this week by the St. Louis Blues as their new director of strategic planning.
 
Key Topics - Red Wings draft picks and strategy - Free agency signings and trades - Player development and prospects - Team identity and future plans - Impact of recent NHL moves
 
00:00 - Flight Cancellations and Scams
02:40 - NHL Draft and Free Agency Overview
05:17 - Analyzing Free Agency Moves
08:09 - The Impact of New Acquisitions
10:40 - Team Identity and Future Prospects
13:28 - Dylan Larkin's Trade Drama
15:57 - Looking Ahead to the Draft
21:31 - Buffalo Draft Experience
23:40 - Victor Plante's Emotional Draft Moment
25:17 - Analyzing JP Hurlbert's Selection
28:16 - Sebastian Cossa Trade Discussion
30:54 - Draft Class Overview and Player Potential
37:32 - Shifting Draft Strategies and Future Outlook
39:26 - Draft Grades and Final Thoughts

Jul 3, 2026

42 min

Jun 26, 2026

29 min

In this episode, Tony and Devin discuss the latest NHL trades, the potential trade of Dylan Larkin, and the Detroit Red Wings' upcoming draft strategy, including key prospects and draft picks. They analyze team moves, draft value, and strategic considerations for building a competitive team.
 
Key Topics:
NHL trade activity and potential Dylan Larkin trade
Red Wings draft strategy and key prospects at 47
Impact of recent trades on team building
Drafting for value versus ceiling in later rounds
Prospect pipeline and defensemen development
NHL Trade Frenzy: Will Dylan Larkin Be Traded?
Red Wings Draft Strategy: Who Should They Pick at 47?
Sound Bites
"If they don't get a deal draft weekend here, it might go into July or August."
"Steve Yzerman will only do a trade if it's right for the organization."
"Shoot for the stars with your second round pick."
Chapters
00:00 - NHL Trade Frenzy: Analyzing Recent Moves
04:44 - Dylan Larkin's Future: Trade Speculations
09:13 - Draft Strategies: The Importance of the 47th Pick
12:13 - Shooting for the Stars: Second Round Picks
16:31 - Late Round Picks: Building Depth for the Future
26:14 - Hypothetical Scenarios: What If Larkin is Traded?
 

Jun 26, 2026

29 min

Jun 19, 2026

48 min

Interview:
Summary
In this episode, Shane Malloy, a renowned hockey scout and author, shares insights on NHL draft strategies, player evaluation, and the Detroit Red Wings' prospects and management. Tune in to learn how to assess talent and build a winning team in hockey.
Keywords
Hockey Draft, Player Evaluation, Detroit Red Wings, Shane Malloy, NHL Prospects, Draft Strategy, Hockey Management
Key Topics
NHL draft strategy and player evaluationDetroit Red Wings prospects and managementImportance of second and seventh round picksMental makeup and leadership in prospectsDefensemen value in draft and trades
 Guest Name: Shane Malloy
Titles
Decoding the NHL Draft: Insights from Shane MalloyHow to Build a Winning Hockey Team: Draft and Development Strategies
Sound bites
"They just don't hit in the second round.""You want those glue guys in the middle.""It's about players who can play five on five."
Chapters
00:00 The Struggles of Second Round Picks02:43 Dylan Larkin's Trade Request and Its Implications05:27 The State of the Red Wings Organization08:31 Prospects and Future Trade Opportunities11:09 Mental Makeup of Prospects14:03 Leadership and Opportunity in the Red Wings16:54 The Future of the Red Wings Post-Larkin22:09 Rising Stars and Leadership Mindset23:18 Draft Strategy: High Floor Players28:54 Identifying Value in the Draft34:23 The Importance of Off-Puck Play41:13 Finding Late-Round Gems43:36 Evaluating Draft Class Strength
Resources
Shane Malloy on Twitter - https://twitter.com/ShaneMalloyThe Art of Scouting by Shane Malloy - https://www.amazon.com/Art-Scouting-Shane-Malloy/dp/XXXXXXNHL Network Radio Sirius XM - https://www.siriusxm.comProspect Profiles on NHL Network Radio - https://www.siriusxm.com/prospectprofiles
Guest links
Twitter - https://twitter.com/ShaneMalloy
 

Jun 19, 2026

48 min

Jun 12, 2026

52 min


 In this week’s episode of The Flying Octopus Podcast, the fellas dive into the latest news surrounding Dylan Larkin’s trade request, including an updated trade list, potential returns, and the impact on his legacy. The discussion then turns to Steve Yzerman and if he’s the right person to be managing the situation on Detroit’s end, plus what a trade (or holding out for a better return) might mean for the Red Wings’ other offseason plans. The guys also discuss the Sebastian Cossa trade rumors that have been circulating as of late and what they potential signal for the organization.
 
WHERE TO FIND US
TWITTER - @FLYINGOCTOPOD
YOU TUBE - @THEFLYINGOCTOPOD
ITUNES, SPOTIFY OR WHEREVER YOU GET YOUR PODCASTS
 

Jun 12, 2026

52 min

Jun 5, 2026

34 min

This episode dives into the emotional and strategic implications of Dylan Larkin's trade request from the Detroit Red Wings. We analyze the potential impact on team dynamics, future prospects, and the broader NHL landscape, featuring insights from hockey experts.
 
Chapters
00:00 The Trade Deadline Rift03:16 Dylan Larkin's Trade Request07:43 Emotional Reactions and Organizational Impact12:16 Future Implications for the Red Wings16:42 Leadership and Fan Reactions19:31 Dylan Larkin's Legacy and Fan Reactions21:53 Steve Yzerman's Strategy and Future Implications24:11 Trade Scenarios and Potential Destinations for Larkin31:50 Trusting the Yzerplan Now?: Yzerman's Decisions Under Scrutiny34:57 The Emotional Impact of Larkin's Potential Departure
 
 guest links:
Twitter - https://twitter.com/HockeywithDevin
 

Jun 5, 2026

34 min

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