Best Companies That Buy Annuities: A CPA’s Guide to Cashing Out

Annuities and structured settlements are safe, predictable, and usually tax-advantaged. From an accounting perspective, they’re some of the most secure assets you can own.

But life rarely sticks to a spreadsheet.

Unexpected debts, tuitions, and medical emergencies can make that future income feel restrictive, leaving you searching for how to sell annuity payments for cash because you need liquidity now — not five years from now.

As a CPA, I generally advise clients to hold onto guaranteed income (it’s a no-brainer, after all). But if you must sell, the most critical variable is not the cash offer; it’s the partner you choose.

Who you sign with determines whether you get a fair deal or pay exorbitant fees hidden in the “discount rate.” A reputable firm will clearly explain their rates and your take-home total. A predatory firm will hide the numbers behind fast cash promises. 

With that in mind, the companies I’ve selected below are ranked based on their reputation for transparency, their history of court approvals, and their ability to execute a compliant buyout.

Top 5 Legitimate Companies That Buy Annuities

The following firms are established players in the secondary annuity market. They have the capital to fund large buyouts and the legal teams to navigate state protection acts.

1. Strategic Capital

Best For: Safety, strategic planning, and partial sales

In an industry aggressive about “cash now,” Strategic Capital operates differently. In my opinion, they position themselves more as settlement planners than mere buyers. And from a financial perspective, their approach is the most aligned with long-term wealth preservation.

They’re known for slowing the process down just enough to ensure the math makes sense for the seller. When you contact them, they don’t immediately push a contract — they evaluate why you need the money.

Why They Stand Out:

• Preserving Income: They often advise clients to sell only what they need (a partial buyout) rather than liquidating their entire policy.
• Compliance & Safety: Strategic Capital does the due diligence to ensure the sale is in your best interest, which improves your chances of approval in court.
• Transparency: They are explicit about their discount rate and fees. You won’t find hidden administrative costs eating into your check at the closing table.

CPA’s Note: If I were advising a client who absolutely had to sell, I would point them here first. Their willingness to walk away if a deal damages your long-term financial health is rare in this sector.

2. Fairfield Funding

Best For: Low fees and personal service

Fairfield Funding has carved out a strong niche as a low-cost provider. They’re smaller than the industry giants, they don’t spend millions on TV commercials, and their cost of acquisition is lower — which allows them to operate with lower overhead. This allows them to pass savings on to the seller in the form of more competitive offers (i.e., lower discount rates).

They focus heavily on customer service and assigning a single representative to handle your file from quote to funding.

Why They Stand Out:

• 100% Guaranteed Close: Fairfield often pledges that they’ll cover all closing costs and court fees, even if the judge denies the transfer. This removes the financial risk from the seller.
• Speed: Because they’re smaller, they can sometimes move faster on paperwork than the bureaucratic giants. Keep in mind, however, that the court docket will ultimately determine how fast you can be funded (this is true no matter who you go with).

CPA’s Note: From an accounting perspective, I appreciate efficiency, and Fairfield’s lean operational model often translates into a lower effective discount rate for the seller.

3. JG Wentworth

Best For: Brand recognition and speed

You likely know their jingle. JG Wentworth is the largest and most recognizable name in the space, so if you value working with a massive corporation that’s seen every possible type of annuity contract, they’re a safe bet.

They have a factory-like efficiency, with systems that are streamlined to process high volumes of transactions. If you have a standard case and need to move as fast as the courts allow, their infrastructure supports that.

Why They Stand Out:

• Reliability: They’re too big to fail on a funding obligation. You know the check will clear.
• Experience: They’ve handled billions in structured settlement payments.

CPA’s Note: Big marketing budgets require big revenue. While they’re a reputable brand, you should always compare their quote to ensure you aren’t paying a premium for the brand name.

4. Peachtree Financial Solutions

Best For: Flexible options

Peachtree is a subsidiary of the same parent company as JG Wentworth, but they operate with a slightly different focus. They’re known for working with people who have more complex financial pictures, including those looking to sell lottery winnings or specific types of difficult annuities.

Similar to a company like Strategic Capital, Peachtree offers a highly educational approach. Their representatives are trained to walk you through different scenarios — for example, selling a lump sum now vs. selling monthly payments for a set period.

Why They Stand Out:

• Versatility: Peachtree buys a wide range of payment streams and offers other financial services like debt consolidation.
• Stability: Being part of a larger family of companies gives them immense financial backing.

CPA’s Note: Specialized transactions often carry higher premiums. If you’re selling a difficult asset that other firms rejected, Peachtree is a capable resource because they understand complex risk.

5. DRB Capital

Best For: Aggressive funding timelines

DRB Capital markets itself on speed, understanding that most people selling an annuity are doing so because they have a pressing financial matter. They also have established internal processes to expedite the filing of court documents.

Just note that they’re aggressive. This can be a good thing because they’ll work hard to get your business and get the deal done. They also often offer pre-settlement advances to get you cash before the court date.

Why They Stand Out:

• Pre-Settlement Cash: If you can’t wait the 45–60 days for court approval, their advance program is a draw — just make sure that accepting the funds doesn’t lock you into a contract.
• High Buyout Caps: They can handle very large policies that smaller firms might struggle to capitalize.

CPA’s Note: Be very careful with advances. They often come with high interest rates or fees that are deducted from your final lump sum. Read the fine print to understand what that advance is actually obligating you to.

The Buyout Process: Safety and Compliance

Understanding the players is only half the battle. To protect your financial interests, you must understand the rules of the game. Selling annuity payments is not like selling a car, after all; it’s a legal transfer of rights that requires judicial oversight.

Here’s how it works.

1. The Quote and Disclosure

You provide the buying firm with your policy details (insurance company name, payment amounts, and dates), and they provide a quote.

By law, they must show you the gross amount (what you’re selling) and the net amount (what you get). A consultative firm focused on financial well-being will encourage you to take this disclosure statement home and review it thoroughly. High-pressure firms will try to get you to sign quickly.

2. The Contract

Once you accept an offer, you sign a purchase agreement. This contract is contingent on court approval, so even if you sign it, you don’t get the money yet and you don’t lose your payments yet.

3. The Cooling Off Period

Most states enforce a waiting period (often 3 to 10 days) after you sign the contract, during which you can cancel the deal without penalty. This is a consumer safety mechanism to prevent emotional decision-making.

4. The Court Petition

The buying company hires an attorney to file a petition in your local county court, asking the judge to approve the transfer of your payment rights to them.

Note: You generally won’t have to pay for this attorney; the buying company does. However, you should be aware that this attorney represents them, not you.

5. The Hearing

This is the most important part of the process. You will appear before a judge, who will ask things like:

• Why do you need the money?
• Is this sale in your best interest?
• Will selling these payments prevent you from paying your rent or feeding your family?

Note that the judge’s job is not to help the company; it is to protect you.

This is where company selection matters. When a company has done its homework, judges often view it favorably. For example, Strategic Capital prepares a detailed “Use of Funds” explanation that demonstrates to the court that the buyout improves the seller’s life (e.g., buying a home, paying off high-interest credit card debt, funding education).

If you work with a predatory firm that submits a bad deal, the judge will reject it. You will be back to square one, having wasted two months.

6. Funding

Once the judge signs the order, it’s sent to the insurance company (the annuity issuer). The insurance company acknowledges the transfer, and the funds are then wired to your bank account.

Things to Keep in Mind When Selling Annuities

Selling annuity payments for cash is a tool. Like any tool, it can help build your future by clearing debt or buying assets, or it can injure you by stripping your long-term security.

As a CPA, my primary concern with annuity factoring is the permanent loss of guaranteed income. Once you sell a payment, it’s gone forever — you can’t buy it back.

This is why I advocate heavily for partial buyouts where you don’t sell your entire annuity; you sell only specific payments:

• Example: You have payments of $1,000/month for the next 20 years and need $50,000 for a down payment on a house.
• The Wrong Way: Sell the whole policy. You get a nice lump sum, but you have zero income next month.
• The Right Way: Sell only the payments for the next 5 years (or sell $500 of the monthly payment for 10 years).

Some firms excel here more than others — some want to buy as much as possible while others are going to focus on what makes sense for you. I would always recommend a firm that solves the immediate cash problem without destroying the long-term safety net. Companies like Strategic Capital have demonstrated that you can operate in this industry with integrity, putting your financial health ahead of their transaction volume.

Bottom line?

1. Prioritize Safety: Choose a firm with a history of court approvals.
2. Demand Transparency: Ensure you understand the discount rate.
3. Preserve Income: Try to sell only what you need.

The market is filled with loud voices and flashy commercials, but ignore the volume and always look at the substance.