Episode 14 - Trade Deadline Strategies
The trade deadline is coming in hot. Whether you’re contending (North), rebuilding (South), or waiting and seeing (East), every move must serve a purpose. Jeff breaks down how to make smart, directional trades before time runs out.
The trade deadline is the moment of truth for every dynasty manager. In this episode, Jeff walks through how your strategic direction—North, South, East, or West—shapes every decision you make when the clock is ticking.
For perennial contenders in the North, it’s about surgical upgrades that strengthen an already strong lineup without mortgaging the future. Rebuilders in the South hold the leverage; they can convert fading veterans into building blocks for next year and beyond—but must avoid overplaying their hand or hoarding picks they can’t actually use. Meanwhile, managers in the East, stuck in wait-and-see mode, often find that patience is the best move of all.
Across every direction, Jeff emphasizes one universal test for any trade: “Can I get this same value later?” If the answer is yes, waiting might be your smartest play. As the trade window closes, knowing your direction—and sticking to it—is what separates strategic managers from reactive ones.
Key Takeaways / Highlights
“Every move at the deadline must serve your strategic direction.”
North: Make surgical upgrades; improve both now and later.
South: Turn fading veterans into future assets—but don’t hoard picks.
East: Standing pat is often the right move.
“You don’t have to trade just because it’s the deadline.”
Universal deadline test: Can I get this value later?
Chapter Timestamps
00:00 — Intro
01:26 — The biggest mistake dynasty managers make
02:07 — Compass refresher
03:16 — Strategies for perennial contenders (North)
05:08 — Three questions for contenders
09:49 — Strategies for rebuilders (South)
12:01 — Three questions for rebuilders
18:58 — Strategies for wait-and-seers (East) & three questions
22:32 — “Can I do this in the offseason instead?”
22:53 — Pressure check by direction
24:02 — Next week: Island of Broken Toys
Related Links & Tools
Listen to this episode on Apple Podcasts or Spotify
Ep. 13: Boosting Your Starting Lineup
Ep. 1: Where Are You Going?
