Caveat: This post is about public policy not investment or personal finance tactics or strategies. As a personal finance matter, Roth accounts are a great way to diversify the tax risk of a retirement portfolio – especially for someone who is sophisticated enough (or has a sophisticated advisor) to use them intelligently. I have a significant share of our retirement portfolios in Roths for precisely that reason.
One of my pet peeves is the misperception1 by sophisticated people of a what I see as a crucial flaw in the Roth structure in how we incentivize retirement savings: the Roth structure piles tax benefits on those lucky enough to be winners in the investment race, while punishing losers. The net result likely makes the structure regressive on a permanent or lifetime income basis. I have written about this twice before in an overly long and obtuse ways here and here (see “The other Roth problems” section of the latter).
A recent X post on an unrelated topic (sequencing risk in retirement savings) and a striking graph in it (see below) provided what I think is strong, indirect evidence for this effect – investment returns can systematically vary a lot by the randomness of when you start and stop retirement investing (largely when you’re born and start working). So, it caused me to once again mount one of my old hobby horses and write this post. Apologies. You can hit delete now, if you aren’t interested in hearing me drone on about this relatively esoteric topic.
Roth versus traditional structure
The incentive or subsidy provided by Roth versus traditional IRAs varies based on whether the subsidy is provided at the point of (1) the contribution or savings (traditional or frontloaded tax benefits) or (2) the distribution or consumption (Roth or backloaded tax benefits). It is well known (pp. 9-10) – based on simple algebra – that the amount of the subsidy is mathematically identical if/when two elements are the same for the entire period of saving and retirement:
- The tax rate on contributions and distributions; and
- The rate of return on the investment
Of course, in the real world we know that those two things are never constant. Legislation changes effective tax rates, as well as individuals’ incomes varying over their lifetimes causes their tax rates to rise and fall. Similarly, we know that investment returns vary widely. This variance results mostly from random stuff: investment skill, luck, or pure timing.2
This post relates to the last of these, timing: even if everyone invested the same amount or percentage of their retirement savings in index funds (eliminating skill and luck as a factor), investment returns will systematically vary based on when they started saving and when they started drawing down their accounts. That variance occurs because of the business cycle, animal spirits, changing expectations, yada, yada.
Why it matters
In my view, this matters crucially on a policy basis because providing the subsidy at the point of contribution is fairer or more equitable.3 That is so because the Roth structure, all else equal, provides larger incentives to individuals who realize above average investment returns. (This gets back to the assumption of a constant rate of return to make the two mechanisms equivalent.) Thus, these lucky ducks (winners in the investment lottery, so to speak) get bigger subsidies, magnifying their higher investments returns. Put another way, the portion of their return that exceeds the average return in the assumption goes untaxed. They get bigger incentives; those with lower returns get smaller incentives on average. Second, one has to assume that folks who realize systematically better investment returns typically have higher incomes, because their accounts end up being larger on average, all else equal. So, the Roth structure makes the tax and retirement system more regressive, compared to the traditional structure.
Birth lottery
A recent interesting X post on a tangentially related subject – sequencing risk in retirement savings – provides an illustration of why this assumption is likely correct and that it is not trivial. (Note: the post is about the variance in investment returns and the effects on retirement savings, NOT taxation.) The post is by Jesús Fernández-Villaverde, a U Penn economics professor, who I had never heard of but assume is a reliable source.
Investment returns vary because of the cyclical ups and downs of the stock and bond markets. There can be long periods of good markets (e.g., the 1990s) and bad markets (e.g., the 1970s). When you start investing/saving for retirement and when you stop and begin drawing down your account matters – potentially by a lot. Fernández-Villaverde did some extensive calculations of those effects and the results are quite striking. The entire X post is well worth reading for those interested in the general topic. It’s short. Here’s his graph that summarizes his results, which show a lot of variation:

Methods and results. His calculations are for a pure stock portfolio (S&P 500 index) for the period 1945-2024. He calculated real returns (i.e., he took inflation out of them). Here’s his description of the results (my emphasis added):
Over this 80-year period, the S&P 500 delivered a geometric mean real total return of about 7.5% per year. That is an impressive number. But this average return masks a lot.
Imagine a worker who starts investing at age 22 and retires at age 68. That gives them 46 years of contributions. In their first year, they contribute $1. Each subsequent year, they increase their contribution by 1% (roughly keeping pace with real wage growth). Every dollar is invested in the S&P 500. They never touch the money until retirement. No panic selling, no market timing, no strategy switching (and no management fees!). Textbook investing and waiting.
I ran this exercise for every possible cohort for which the data allow. The first cohort starts investing in 1945 and retires in 1991. The second starts in 1946 and retires in 1992. And so on, all the way to the last cohort, which starts in 1978 and retires in 2024. This yields 34 cohorts, each investing for 46 years, making the same contributions and investing in the same index. The only difference among them is which 46-year slice of historical returns they happen to live through.
The most fortunate cohort, the one that started investing in 1954 and retired in 2000, had $607 on the day of retirement (remember, all in real terms), with a real annual return of 8.82%. The unluckiest cohort, the one that started in 1963 and retired in 2009, accumulated $210, with a real annual return of 4.83%. Same contributions. Same index. Same strategy. Same investment horizon. Yet the luckiest retiree ended up with 2.9 times more wealth than the unluckiest. 4
The typical retirement account is not invested 100% in stocks, which provide a higher rate of return than bonds or cash. Conventional wisdom warns against an all-stock portfolio, especially as retirement approaches. So, his assumption exaggerates the difference between the highest and lowest returns. He redid it using a target date fund. This reduced the 2.9X difference to 1.6X.5 That is still a large difference.
He also points out that in the real world, the ones with unlucky timing relative to the business cycle will suffer more than just subpar investment returns:
In fact, sequencing risk is even worse because poor returns in the stock market are correlated with weak labor markets: you have a much higher probability of losing your job (or seeing your wage income fall) precisely when the market is doing poorly, preventing you from saving when prices are low and equities are most attractive. However, let me set that point aside today to simplify the exposition.
Policy implications. To me, this illustrates one policy reason why the Roth structure is flawed as a retirement incentive: it piles larger tax benefits on those lucky enough to realize above-average investment returns (investment skill, pure luck, or as here when they started and ended their retirement savings) who need it least. Higher returns are almost certainly correlated with higher retirement incomes, probably strongly correlated.6 This undoubtedly makes the tax and retirement systems less progressive. It persists across age cohorts, if you look at the pattern of the graph.
I can think of no countervailing policy reason for giving more to investment winners and less to investment losers. It does not incent desirable behavior (like savings or careful investing), rather random luck. Moreover, Fernández-Villaverde’s calculations make it clear what we’re often rewarding is simply timing, mainly the timing of one’s birth which no one controls. If anything, a better policy is to offset the effects of bad luck. The traditional IRA structure does that by the government assuming some of the risk of random variance in investment returns, while the Roth structure works in the opposite direction.
We’d have been much better off if Senator Roth and President Clinton had never started us down path of using the Roth structure. Unfortunately, it’s now too late. Because the Roth structure allows Congress to game the measurement of fiscal cost, it makes further movement to Roths fiscally irresistible as Congress almost surely enacts future editions of the Great American Retirement Fraud. (See my summary here.)
Of course, there are a host of other reasons for criticizing the retirement incentive system. It’s too complex, too expensive, gives a lot of help to those who don’t need it, is tilted to the affluent, etc.
Notes
- Maybe systematic ignoring would be a fairer way to characterize it. ↩︎
- See the classic book, Burton Malkiel, A Random Walk Down Wall Street for chapter and versus. Reading it in the early 1980s transformed my approach to investing and put me on the path to prosperity in retirement FWIW. ↩︎
- There are IMO a host of other flaws with the tax incentive system for retirement savings. Among them: Requiring people to choose between Roth and traditional structures creates immense complexity and adds a lottery effect to the amount of the benefit received. The Roth structure encourages policy makers to undercount the fiscal cost of providing retirement incentives compared to the traditional structure, because it pushes cost outside the budget window. Because the size of incentives rise with tax rates, both types give bigger incentives to individuals with higher incomes and tax rates, those who are less likely to need them. Affluent people typically save without incentives. That only scratches the surface of the policy problems with our system of retirement incentives. ↩︎
- Of course, comparing the worst and best case provides an exaggerated view of the difference. A more balanced approach would look at the statistics measuring the dispersion or variance in the return. Because this is a post on X, he didn’t provide that type of detail. The graph appears to show a lot of variance, and the pattern of the bars show that some age cohorts are systematic losers or winners. I personally happen to be in age cohort winners FWIW. ↩︎
- My observation is that his glide path allocation much more aggressively shifts to bonds than the typical one used by Fidelity, Vanguard, etc. He has the stock allocation at 20% at the time of retirement. Vanguard and Fidelity’s target 2025 funds have their stock allocations set between 50% and 60%. So, the actual reduction is probably smaller than he suggests. ↩︎
- This is what I would like to see data analysis on to potentially validate my inferences. ↩︎