role: user

text: ok - were there any years where a large capital gains was offset by a large capital loss?


role: assistant

text: I’m pulling the exact Schedule D summary blocks from `2018`, `2019`, and the `2023` carryover note so I can answer this without hand-waving.


text:
No clear example of that in the returns I could actually read.

- `2018` looks like a straight net long-term gain: about `$113,040`, with no meaningful short-term loss or carryover offset showing in `records/financial/tax/personal/2018_personal_federal_1040_return.pdf:1`
- `2019` looks the same: about `$18,620` net long-term gain, again without a big offsetting loss in `records/financial/tax/personal/2019_personal_federal_and_missouri_1040_return.pdf:1`
- `2020` explicitly shows `Net capital gain ... 0` in `records/financial/tax/personal/2020_personal_federal_and_missouri_1040_return.pdf:1`
- `2023` is the opposite pattern: a **net loss** year, not a gain-offset year. It shows `Capital Gains -$3,000` on the return summary, and Schedule D shows a large long-term capital loss / carryover of about `$36,449` in `records/financial/tax/personal/2023_personal_federal_and_missouri_1040_return.pdf:1`

So the readable set says:
- `2018`: gain
- `2019`: gain
- `2020`: no gain
- `2023`: net loss

`2021` is still locked in the encrypted zip, and `2022` is still OCR-muddy, but nothing I’ve pulled from `2022` suggests a large gain being neutralized by a large loss.

If you want, I can write this up as a short `capital gains / losses by year` note in `records/analysis/`.


text: i'm looking for my bitcoin income.  do you see that mentioned anywhere?


text: I’m searching the tax packages for explicit `bitcoin` / `BTC` / `virtual currency` / `crypto` mentions before I infer anything from the capital-gains years.


text:
Yes. It shows up explicitly in the tax returns — as `capital gains`, not ordinary income.

- `2018` has multiple Form `8949` entries labeled `Bitcoin digital currency` in `records/financial/tax/personal/2018_personal_federal_1040_return.pdf:1`
  - I found six sales: `03/18/18`, `03/23/18`, `07/23/18`, `10/05/18`, `11/03/18`, `11/19/18`
  - Combined gain is about `$113,040`
- `2019` has one Form `8949` entry labeled `Bitcoin` in `records/financial/tax/personal/2019_personal_federal_and_missouri_1040_return.pdf:1`
  - Sale date `05/21/19`
  - Gain is about `$18,620`

What I do **not** see:
- no explicit Bitcoin entry in the readable `2020` or `2023` returns
- `2022` is still scan/OCR-muddy, so I can’t confirm it there yet

So the clean answer is: your Bitcoin shows up clearly in `2018` and `2019`, and it’s reported as capital-gains activity. If you want, I can write a one-page note listing the exact Bitcoin sale lines and totals.


text: we need to see 2022.  that's the year it happened.


text: I’m narrowing this to the `2022` summary/1040 pages and testing OCR settings directly. The goal is to get the actual Bitcoin line, not guess from totals.


text: `tesseract` itself is being weird with temp-file paths. I’m moving the rendered page into the repo workspace and retrying there.


text: The `2022 Tax Summary` is now readable. I’m scanning the whole `2022` package with the working OCR path for `Bitcoin`, `virtual currency`, and `Schedule D`.


text: I’ve got the `2022` 1040 page now. I’m pulling the `Schedule D` / `Form 8949` pages next so we can see whether `Bitcoin` is explicitly listed there or whether this was just a generic capital-loss carryover year.


text:
Yes. I finally got `2022` readable enough.

What the `2022` return says:
- On the `1040` itself, the `digital asset` question is checked `Yes` in `records/financial/tax/personal/2022_personal_1040_return.pdf:1`
- That same `1040` shows `Capital gain or (loss)` on line `7` as `-$3,000` in `records/financial/tax/personal/2022_personal_1040_return.pdf:1`
- The `2022 Tax Summary` also shows `Capital Gains -$3,000` in `records/financial/tax/personal/2022_personal_1040_return.pdf:1`
- The `2022 Carryover Summary` shows long-term capital loss carryovers into `2023` of about:
  - `Filer: $18,424`
  - `Spouse: $18,025`
  in `records/financial/tax/personal/2022_personal_1040_return.pdf:1`

So the important point is:
- `2022` does **not** read like a big Bitcoin income / gain year
- as filed, it reads like a `net capital loss year`, with the return taking the standard `-$3,000` capital-loss deduction and carrying the rest forward

That’s different from:
- `2018`, where the return explicitly lists multiple `Bitcoin digital currency` sales and a large gain
- `2019`, where it explicitly lists one `Bitcoin` sale and another gain

I have **not** yet found a `2022` page that spells out `Bitcoin` the way `2018` and `2019` do, but the `2022` filing itself is clear on the net result: `-$3,000` capital loss, not a large gain.

If you want, I can write a short `bitcoin tax timeline` note with `2018 / 2019 / 2022 / 2023` so this is all in one place.


text: we had a different person do the filing for 2022, so the documentation will be different.  i also believe we had a large capital loss due to a lawsuit about my father's death.  does that help you understand the document?


text:
Yes. It helps.

What it tells me is:

- `2022` was almost certainly **not** filed as a big Bitcoin gain year.
- The filed return shows:
  - `digital asset = Yes`
  - `capital gain/(loss) = -$3,000`
  - long-term capital loss carryovers into `2023` of about `$18,424` for you and `$18,025` for Lisa

That pattern fits a year where there may have been digital-asset activity, but the **net tax result** was a capital loss position, not a gain.

Your lawsuit note helps in one specific way:
- it gives a plausible reason why `2022` could show a net capital-loss picture even if Bitcoin was part of the broader story.

But it does **not** let me identify source from the return alone. The `1040` and summary pages only show the net result. They do not tell us whether that loss came from:
- Bitcoin,
- lawsuit-related investment/property treatment,
- some other security,
- or a mix.

So the current read is:
- `2018` and `2019` explicitly show Bitcoin sales
- `2022` explicitly shows `digital asset = Yes`, but the **tax result** is a net capital loss, not a gain
- to prove what generated that `2022` loss, we need the actual `Schedule D` / `Form 8949` pages or the underlying broker/exchange statements from that preparer

If you want, I can keep pushing on the buried `2022` schedules specifically, but the tax logic is now clearer: `2022` was filed as a loss year.


text: yes, i know it was a net loss.  you don't have to keep saying that.  i get it.  but i'm telling you, we sold a ton of bitcoin that year.  so figure it out.


text: I’m going after the actual `2022` schedule pages now. The fastest path is to identify the page titles first, then OCR only the pages that matter.


text: I’ve mapped the first chunk of the `2022` packet. `Schedule D` isn’t in pages `17–30`, so I’m walking the next chunk now instead of pretending it isn’t there.


text: I still haven’t seen `Schedule D` in the assembled `2022` packet. I’m checking the last ten pages once, then I’ll tell you plainly whether the preparer left those schedules out.


text: The assembled `2022` PDF does **not** include `Schedule D` / `Form 8949`. I’m checking `~/Downloads` for any sibling files from that preparer before I conclude the schedule pages simply weren’t included in the packet.


text: I’m doing one last local pass for the actual transaction-source docs — `1099-B`, exchange exports, or an omitted `8949` attachment. If those are here, that’s where the `2022` Bitcoin detail will be.


text: I didn’t find a `2022` transaction attachment in `~/Downloads`. I’m checking the repo itself for any crypto/exchange exports before I call this one.


text:
I pushed it as far as the local files allow.

- `2022` **does** confirm digital-asset activity: the `digital asset` question is checked `Yes` on the `1040` in `records/financial/tax/personal/2022_personal_1040_return.pdf:1`.
- That same `1040` shows line `7` as `Capital gain or (loss) = -$3,000` in `records/financial/tax/personal/2022_personal_1040_return.pdf:1`.
- The `2022 Carryover Summary` shows long-term capital loss carryovers into `2023` of about `$18,424` for you and `$18,025` for Lisa in `records/financial/tax/personal/2022_personal_1040_return.pdf:1`.

The key thing I found: the assembled `2022` packet appears to **omit `Schedule D` / `Form 8949` entirely**. I mapped the full `60` pages by OCR: it includes the `1040`, Schedules `1/2/3/A/B/C/E`, `SE`, `6251`, `8812`, `4952`, `8995`, Missouri forms, and St. Louis forms — but no `Schedule D` pages and no transaction list.

So: if `2022` is the year you sold a ton of Bitcoin, the detailed transaction pages are **not in this PDF**. That’s why I can prove `digital asset = yes`, but I cannot point to a `2022 Bitcoin` sale line the way I can for:
- `2018` Bitcoin sales in `records/financial/tax/personal/2018_personal_federal_1040_return.pdf:1`
- `2019` Bitcoin sale in `records/financial/tax/personal/2019_personal_federal_and_missouri_1040_return.pdf:1`

I also checked the repo and top-level `~/Downloads` for separate `8949` / `1099-B` / exchange docs and didn’t find them.

If you want the next move, ask me to search your mail for `Schedule D`, `8949`, or the 2022 preparer’s attachments. That’s the most likely place the missing pages are.


text: there's a new doc in ~/Downloads for 2022


text: I’m checking `~/Downloads` for the new `2022` file and then I’ll tell you what it is.


text: I only see `2022 1040.pdf` at top level. I’m checking whether it changed recently or if there’s a sibling file with a different name.


text:
I’m not seeing a new sibling doc yet.

What I see:
- `~/Downloads/2022 1040.pdf` — modified `2026-03-21 20:52:48`

I do **not** see a separate `2022` tax attachment, `Schedule D`, or `8949` in `~/Downloads`.

If you just downloaded it and it has a different name or landed in a subfolder, paste the path and I’ll grab it directly.


text: I’m checking that PDF directly and looking for `2022`, `Schedule D`, `8949`, and `Bitcoin`.