Biden proposing 44.6% capital gains tax - highest rate since it was created in 1922!

So my regular income wouldn't push me anywhere near that million-dollar threshold. Even with the stocks I'm planning to sell (probably around $65k worth), I'd still be way below that level. That's a relief! Would it make sense to spread the sales across two tax years to keep my total income lower each year? I'm wondering if that might help me stay in a lower capital gains bracket.

Spreading your stock sales across two tax years is definitely a smart tax planning strategy. By doing this, you might be able to keep more of your capital gains in the 15% bracket instead of potentially pushing some into a higher bracket in a single year. For your situation, with $97k income and roughly $65k in stock sales, you'd still be comfortably in the 15% long-term capital gains bracket even if you sold everything in one year. But splitting the sales could help with overall tax planning and might give you more flexibility with other deductions or credits you might be eligible for. Just make sure you're considering your entire tax situation, including any other income or deductions that might affect your total taxable income.

How accurate is this tool? I've been burned by online calculators before that didn't account for all the details of tax law. Does it just give general info or can it actually look at your specific situation?

I'm skeptical about putting my tax info into some random website. How do you know it's secure? And are they just trying to sell you tax services at the end?

The tool is surprisingly accurate because it references the actual IRS tax code and recent proposals. It's not just a generic calculator - it analyzes the specific policy details and explains how they apply to different income scenarios. I found it much more detailed than the usual online calculators. Regarding security concerns, I didn't have to enter sensitive personal information like SSNs or account numbers. You just input income ranges and investment types. The site uses encryption and doesn't store your documents after analysis. They don't try to sell you additional services - it's a straightforward tool that gives you information about how tax policies affect your specific situation.

How does this actually work? It sounds too good to be true. The IRS phone system is notoriously impossible to navigate.

This sounds like a scam. Why would I pay someone else to call the IRS for me? And how do they magically get through when no one else can? I'm highly skeptical that this is legitimate.

It works by using an automated system that navigates the IRS phone tree and waits on hold for you. Instead of you personally waiting on hold for hours, their system does it. When an actual IRS agent picks up, you get a call connecting you directly to that agent. It's basically like having someone else wait in line for you. The reason they can get through when individuals struggle is volume and technology. They have multiple lines calling simultaneously and systems that know exactly when call volumes are lower. They're not doing anything that bypasses normal IRS procedures - they're just more efficient at working within the existing system. Many tax professionals use similar services because time spent on hold is money lost for them.

You're glossing over important context here. The economy and investment landscape in the 1970s was completely different than today. Many more middle-class people are invested in the market now through 401ks and IRAs. Plus, what starts as a tax on the wealthy often trickles down to impact everyone eventually.

You're right that the investment landscape has changed since the 1970s, but you're missing a critical point: retirement accounts like 401ks and IRAs aren't subject to capital gains taxes at all. They're either tax-deferred (traditional) or tax-free for qualified withdrawals (Roth). These proposed changes would have zero effect on most middle-class retirement savings. As for the "trickle down" tax concern, capital gains tax rates have historically been quite stable for middle income brackets. The 15% rate that most middle-class investors pay has remained consistent for decades across both Republican and Democratic administrations. The changes nearly always happen at the top brackets, not the middle ones.

The capital gains tax rate has varied significantly throughout history. Under Reagan, the Tax Reform Act of 1986 actually raised the maximum capital gains rate to 28% (up from 20%). Under Clinton, it was lowered to 20% in 1997. George W. Bush reduced it to 15% in 2003. Under Obama, it went up to 20% for high earners, plus the 3.8% Net Investment Income Tax was added as part of the Affordable Care Act, bringing the effective rate to 23.8% for high-income individuals. The highest capital gains rate was actually around 35% in the late 1970s before Reagan's first round of tax cuts. The 44.6% rate would indeed be the highest since the tax was created, though it would only apply to those making over $1 million annually.

Thanks for that historical breakdown! Really helpful to see how the rates have changed over different administrations. So if I understand correctly, we've basically been in the 15-28% range for most modern history, with some additional taxes added more recently that brought it to around 23.8% for high earners. The proposed 44.6% would be a significant jump from where we've been for the last several decades, even if it only affects millionaires. I'm curious to see if Congress will actually pass something this high or if they'll negotiate it down.