TAX-LOSS POUNCING (November 23, 2025): I am sure that by this time you have either heard from your accountant or read numerous articles about how you can save on your 2025 income taxes by doing tax-loss harvesting. The idea is to sell whichever shares you own that have lost the most in percentage terms in sufficient quantity so that your capital losses from those sales offset at least 100% of your total 2025 capital gains. That way, you won't owe any capital gains taxes when those are computed in February or March 2026. On paper, this sounds great: you can pay less tax in a few months. It also has the huge side benefit of your spouse not shaking their heads each time you log in and saying, gee, honey, I can't believe you're still holding onto this hopeless underperformer that keeps showing a big red negative change.
Tax-loss harvesting saves you one year's interest at best and often results in converting long-term capital gains to short-term gains the following year.
Clearing out those pesky losing shares so you don't have to look at how much money you lost on them is one of the main reasons people sell losing shares more aggressively at this time of the year. Harvesting tax losses are a convenient excuse for closing out losing positions before the new year. However, there are several serious flaws with this approach. If you sell shares at a loss and then buy them back after more than 30 days to avoid the wash sale restrictions, then you have changed your starting date from earlier in 2025 or from a previous calendar year to November 2025. If you are fortunate to get a powerful bounce in 2026, then unless you hold those shares until at least one year and one day after you have bought them, you will have ended up converting a low-taxed long-term capital gain into a highly-taxed short-term capital gain. This will result in paying much more in additional taxes the following year than you had saved by claiming a tax loss in the current calendar year, only gaining several months of interest on your taxes due.
You might feel emotionally better for not having to look at big unrealized losses when you log in, but you are probably mostly selling out-of-favor undervalued shares where insiders are buying and you should be buying too.
Whenever you sell losing shares for alleged tax savings, you will usually end up unloading those shares which are the most depressed in price, which insiders are probably buying the most aggressively, and which are trading near multi-year lows since that is why you chose them for tax-loss harvesting in the first place. Those shares will usually be among the biggest winners during the following year or so. If you don't buy them back after the wash-sale period ends, then you miss out on any strong rebound; if you buy them back and they recover so sharply within a year or less that you choose to sell them, then you have converted what would have been long-term capital gains into short-term capital gains.
Now is the best time of year to eagerly accumulate those shares which have been the most aggressively targeted for tax-loss harvesting. I love to buy shares which have been retreating for two or three years since many investors are more likely to emotionally conclude that a powerful rebound is hopeless.
There are numerous shares which have been especially depressed and are excellent bargains which top executives have been snapping up at their most aggressive pace in many years. In this essay I will identify those shares which I had notified subscribers from November 17 through November 20, 2025 via email to encourage subscribers to progressively accumulate them, using ladders of good-until-canceled purchase orders since they could continue to drop further in the short run. I had mentioned a few of them in my previous blog from one week ago.
MOH is an unpopular stock in an untrendy sector.
One area of the financial markets where investors have been mostly selling instead of buying is in healthcare insurance. Molina (MOH) had reported somewhat disappointing earnings in a relatively small part of their portfolio which receives significant government assistance, and the recent Congressional dispute about extending health insurance credits for middle-income families temporarily depressed their earnings. Once the price fell to a multi-year low, many investors sold because they saw others selling, were disappointed, and joined the usual tax-loss frenzy, thereby creating an excellent buying opportunity which I mentioned in my previous update. I am continuing to purchase this into pullbacks below 140, with the price briefly touching its lowest point since April 3, 2020 near the height of the coronavirus panic.
VAC is an underappreciated stock in the currently unpopular vacation sector.
With some middle-class families recently cutting back on their discretionary spending including vacation travel, a number of shares in this sector have fallen to multi-year lows including Marriott Vacations Worldwide (VAC) which slid to its lowest point since March 23, 2020 during the most intense part of the initial coronavirus frenzy when some people thought we'd all never go on vacation again. There has been recent multiple insider buying which is always a positive signal, combined with tax-loss selling by investors delighted to be able to save on their 2025 taxes no matter how serious a mistake they have been making with their portfolios. I will continue to purchase VAC into pullbacks using ladders of good-until-canceled orders at gradually higher lows, a useful approach during any potential bottoming process.
SG had been a meme stock a year ago and then collapsed near its all-time bottom.
The restaurant chain Sweetgreen (SG) became a meme stock just over a year ago and surged in price, encouraging many top corporate insiders to aggressively sell. Recently some insiders have been buying to take advantage of this stock transforming itself from a social media favorite to a tax-loss favorite. SG recently traded near 5 dollars a share and recently made higher lows near 6, and in between surging higher and sliding lower could make additional higher lows which are almost always worth buying whenever a given stock is depressed.
OGN continues to generally be depressed and has sported a low price-earnings ratio.
You can spend all day reading negative stories about Organon (OGN), but the company has real earnings and multiple top executives who have been buyers in recent months. The stock was being aggressively sold even before the fourth quarter and periodically suffers sharp pullbacks as is common with losing stocks when the most popular large-cap U.S. shares are experiencing a bubble. I had already been purchasing OGN a few months ago, and added more when the share price became even more depressed.
CAG remains a solid choice with compelling fundamentals.
I have mentioned Conagra (CAG) previously on Seeking Alpha, and it remains an untrendy non-AI choice in today's environment with compelling fundamentals. I would be even more aggressive if there were to be more notable insider buying any time soon. You would definitely recognize several of their products from having been around for decades in grocery stores and supermarkets.
LYB is a premier performer in a very untrendy sector.
Many chemical companies have been out of favor and have fallen toward or below multi-year lows, so I decided to purchase only those which had very recent insider buying. LyondellBasell (LYB) fits this description perfectly, having fallen about half from its previous highs and recently attracting additional selling for tax-loss reasons. The company has been a leader in the industry for a long time, so it is an ideal opportunity to take advantage of its unpopularity and as with everything else to use a ladder of good-until-canceled purchase orders to do so in case it has additional downward spikes as bottoming shares often do.
HUN is in the same industry as LYB and has been even more depressed.
Huntsman (HUN) fell roughly 80% from its previous peak which is one of the biggest percentage losers in this sector. It has featured insider buying which is a big positive, and I would buy more aggressively if more insiders were to step up to the plate and make meaningful purchases. The company has dealt with many challenges, while in the short run it has been attracting heavy tax-loss selling since its percentage losses have been so high.
There are roughly two dozen other names which I will probably buy at some point between now and the end of 2025.
In some cases we have compelling valuations combined with multi-year lows but no recent insider buying; as soon as some top executives jump in, I will do likewise and post those positions here on Seeking Alpha. If you believe that any particular stocks are worthwhile for purchase and are similarly out of favor, please let me know as soon as possible. I always appreciate learning from others; several of the names on this list and a number of my favorite purchases during the April 2025 panic were originally pointed out to me by other people.
Continue to gradually rebalance your portfolio which is especially necessary whenever we are passing through the phases of a major bubble.
While many other investors have been congratulating themselves for their brilliance in continuing to purchase stocks which are trading at four, five, or more times their long-term average levels based upon their profits, this has become an especially dangerous time to own such popular shares since many of them could drop 80% or more and still not be undervalued. Ensure that you keep between 60% and 65% of your total liquid net worth in U.S. government debt, while balancing the remainder between stocks with meaningful insider buying that are trading near multi-year lows along with short positions and/or unleveraged bear funds if you have experience in handling their volatility. Whenever Treasuries dip in price, buy more of whatever is cheapest; whenever stocks make extended gains, do some selling; whenever there is a protracted pullback combined with panic such as we had in April 2025, aggressively buy a combination of whatever is most undervalued. In April 2025 this partly involved buying depressed energy shares including Transocean (RIG) which has since more than doubled, along with especially unpopular emerging markets like Brazil and South Korea which had featured numerous bargains. I have been slowly reducing some of those long stock and stock fund positions following impressive gains.
30-year TIPS continue to be among the best conservative bargains in the world.
In contrast with individual stocks which will often fluctuate sharply in price, 30-year TIPS are relatively boring and that is precisely what makes them so appealing. The current yield is about 2.52% fixed for 30 years combined with the urban consumer price index which fluctuates each month. If inflation is running near 3.0% then this means your total yield will be 5.5% which is exempt from state and local income tax. If inflation drops toward or below zero then you will continue to get a minimum of 2.5%, and the yield could be significantly higher if we experience above-average inflation at various points during the next three decades. The last auction for 30-year TIPS had featured their highest fixed yield (2.650%) since 2001 and the yields remain significantly above their long-term averages.
Most fundamental valuations for U.S. stocks are either near or at their highest-ever historic levels going back to 1880:
All U.S. large-cap stock bubbles were followed first by a collapse of more than 80%, and second by a multi-year impressive bull market where value shares generally far outperformed growth shares:
Following the U.S. large-cap bubbles of 1836-1837, 1872-1873, 1928-1929, 1972-1973, and 1999-2000, we first had a two- or three-year severe bear market and then several years of dramatic gains for value shares. This may be because losses exceeding 80% for many popular large-cap shares during their bubble collapses dissuaded investors from quickly getting back into most of their previous growth favorites. For this reason, the vast majority of the shares I have been and will be recommending for purchase during 2025-2029 will be underpriced value shares with meaningful insider buying rather than growth shares.
Incrementally adjust to whatever the global financial markets have been doing:
Since 1981 I increase the ratio of short to long stock positions the more overpriced the U.S. stock market is and the more aggressively that top corporate insiders have been selling. I proportionately increase the ratio of long to short stock positions whenever recent extended selling has enabled worthwhile bargains to be created and insiders have been eagerly accumulating those bargains. Whenever we have a multi-year high in overall insider buying relative to insider selling by top executives, I generally close out all of my short positions.
Disclosure of current holdings:
Below is my current asset allocation as of 4:00 p.m. on Friday, November 21, 2025. Each position is listed as its percentage of my total liquid net worth.
I extracted the totals for each position and grouped these according to sector.
The order is as follows: 1) U.S. government bonds; 2) shorts; 3) bear funds; 4) precious metals; 5) emerging-market funds; 6) individual Brazilian ADRs; 7) energy; 8) other individual shares.
VMFXX/TIAA Traditional, TIAA money market/bank CDs/FZDXX/FZFXX/SPRXX/SPAXX/BPRXX/Savings/Checking long: 35.08%;
17-Week/52-Week/26-Week/13-Week/2-Year/8-Week/3-Year/5,10,30-Year TIPS/4-Week/6-Week/20-Year: 26.50%;
TLT long: 11.91%;
I Bonds long: 3.95%;
LTPZ long: 0.75%;
EDV long: 0.52%;
PMM long: 0.01%;
XLK short: 33.62%;
QQQ short: 25.50%;
GDXJ short: 2.05%;
SMH short: 1.41%;
GDX short: 0.42%;
AAPL short: 0.16%;
PSQ long: 3.12%;
SARK long: 0.33%;
Gold/silver/platinum coins: 11.86%;
PALL long: 3.40%;
FLBR long: 0.84%;
EWZ long: 0.75%;
EWY long: 0.25%;
FLKR long: 0.20%;
TUR long: 0.03%;
EWZS long: 0.02%;
UGP long: 0.60%;
VALE long: 0.44%;
GGB long: 0.23%;
BBD long: 0.20%;
RIG long: 0.80%;
WTI long: 0.13%;
PTEN long: 0.05%;
MOH long: 1.10%;
CAG long: 0.45%;
LYB long: 0.42%;
HUN long: 0.40%;
VAC long: 0.33%;
SG long: 0.28%;
OGN long: 0.24%;
CLF long: 0.01%.
