Our tracked universe gained a median 91% over the eighteen months of daily history we hold, and sealed product hasn't traded below retail in years. In a market like that, how did anyone lose money? Three ways, it turns out — each measurable, each recurring, and each still operating today. This is the loss ledger of the hobby: the round trips, the grading submissions that were mathematically doomed before the box shipped, and the sealed products that spent a decade earning less than the boxes sitting next to them.
The round trip: buying the vertical move
The deepest losses in our data didn't come from bad cards. They came from good cards bought at the top of vertical moves. The Umbreon complex is the textbook: when the Moonbreon halo peaked in early 2025, every Umbreon printing repriced together — and then unwound together. A raw Neo Discovery Umbreon that touched $1,800 trades at $160 today. Aquapolis Umbreon halved. Unseen Forces Umbreon ex halved. Even Base Set Charizard — a card UP over many windows — round-tripped from an $823 peak to $250, a 70% drawdown for whoever bought the spike. The card didn't fail; the entry did.
Worst drawdowns from the 2025–26 peak (raw, 14-day medians)
| Card | Peak | Now | Drawdown |
|---|---|---|---|
| Umbreon · Neo Discovery | $1,800 | $160 | −91% |
| Charizard · Base Set | $823 | $250 | −70% |
| Kyogre & Groudon LEGEND · Undaunted | $499 | $210 | −58% |
| Umbreon · Aquapolis | $700 | $310 | −56% |
| Umbreon ex · Unseen Forces | $1,000 | $500 | −50% |
| Rayquaza ex · Dragon | $405 | $210 | −48% |
| Bianca · Boundaries Crossed | $332 | $188 | −44% |
| Koraidon · SVP Black Star Promos | $93 | $54 | −42% |
The second cluster in the loss column is subtler: launch-window chase cards. Six of our fourteen worst full-window performers are Prismatic Evolutions hits bought at release pricing in January 2025 — Flareon ex (−34%), Dragapult ex (−30%), Jolteon ex (−29%), Roaring Moon ex (−25%), Espeon ex (−24%). Launch supply arrives for months after launch demand peaks; paying week-one prices for a modern chase has been a reliably losing trade in every recent set, even inside sets that remain popular.
The round-trip exhibits — live pricing on every tile
Negative-EV grading: paying $22 to lose $2,000
Grading feels like free upside. The registry says otherwise. For every pop-rich card in our universe we computed the expected value of a raw submission — real PSA grade distributions weighted by real per-grade sale medians, minus the raw price and a $22 fee. Fifteen cards came out NEGATIVE, and they share a profile: vintage raws whose near-mint price already includes the market's hope of a gem, attached to gem rates under 10%. A raw Shining Tyranitar costs about $4,250; its pop-weighted expected slab value is $2,265. The submission destroys $2,007 in expectation before the box ships. Overall, 31% of WotC-era cards in our screen grade at negative expected value — versus 2% for Scarlet & Violet.
The negative-EV grading screen (pop-weighted, $22 fee, anomalies excluded)
| Card | Raw | Gem odds | PSA 10 | PSA 9 | Expected edge |
|---|---|---|---|---|---|
| Shining Tyranitar · Neo Destiny | $4,250 | 5.6% | $18,990 | $2,125 | −$2,007 |
| Shining Celebi · Neo Destiny | $1,801 | 7.5% | $4,118 | $1,821 | −$564 |
| Shining Mewtwo · Neo Destiny | $3,000 | 6.0% | $11,750 | $4,550 | −$526 |
| Shining Kabutops · Neo Destiny | $1,400 | 9.1% | $4,375 | $947 | −$455 |
| M Gengar-EX · XY Promos | $273 | 3.3% | $640 | $200 | −$202 |
| Dark Scizor · Neo Destiny | $595 | 2.5% | $5,300 | $826 | −$172 |
| Dark Charizard · Team Rocket | $176 | 2.6% | $1,563 | $301 | −$28 |
| Charizard VMAX · Champion's Path | $233 | 69.7% | $285 | $166 | −$11 |
Share of cards grading at NEGATIVE expected value, by era
Cards the math says NOT to grade
Sealed: nothing died — but the trinket boxes lagged for a decade
Here is the honest surprise: we could not find a single Elite Trainer Box, across 167 tracked, trading below its $49.99 retail price. Nominal losses in sealed have been nearly impossible this decade if you paid retail. The failure mode in sealed is RELATIVE: products whose contents don't scale. Pin collections, promo-tin formats, and trinket boxes ship with two or three fixed packs plus merchandise the market never reprices. Champion's Path pin collections — same set, same year as that Charizard VMAX — turned $24.99 of 2020 retail into about $47 today, roughly an 11% annual return, while pack-dense and chase-promo products from the very same product families compounded at two to three times that rate. Nobody lost money; half the return evaporated by holding the wrong FORMAT of the same set.
The lagging sealed class — promo/pin formats vs pack formats (5–7 year holds)
| Product | MSRP | Today | Multiple | ≈CAGR |
|---|---|---|---|---|
| Champion's Path Pin Collection (Hammerlocke) | $24.99 | $46.50 | 1.9× | ~11% |
| Champion's Path Pin Collection (Ballonlea) | $24.99 | $46.98 | 1.9× | ~11% |
| Shining Fates Mad Party Pins (Bunnelby) | $24.99 | $40.31 | 1.6× | ~9% |
| Shining Fates Mad Party Pins (Polteageist) | $24.99 | $46.11 | 1.8× | ~12% |
| Shining Fates Mini Tin (Reshiram) | $9.99 | $33.08 | 3.3× | ~25% |
| Hidden Fates Tin (Charizard GX) | $19.99 | $155.74 | 7.8× | ~34% |
The bottom two rows are the control group: tins whose value IS their packs (Shining Fates minis) or their chase promo (Hidden Fates Charizard GX) compounded at two to three times the rate of the pin formats from the same product families. The pattern held all decade: sealed value scales with pack content and chase equity, not with accessories.
Same sets, opposite outcomes
Price histories are daily market-price series over the longest window our data supports per card (January 2025 – July 2026; 425 cards with ≥200 daily points, $10 floor); 'peak' and 'now' are 14-day medians, so single-day spikes cannot create a fake drawdown. Decade-scale sealed figures use documented retail prices (MSRP) against current tracked prices, with CAGR approximated over each product's years since release. Grading EV = pop-weighted expected slab value (true PSA registry grade shares × per-grade eBay sale medians, ≥3 sales per grade; sub-8 outcomes haircut to 55% of the 8) minus raw market price and a $22 grading fee; grade-inverted or >40× comp anomalies excluded rather than smoothed. All linked product pages price continuously and will drift from captured figures. Nothing here is financial advice.