A few days ago, the FT published an interesting article about the 2023 Carvana out-of-court restructuring where Apollo took a $1.3bn haircut on $5.6bn of unsecured junk bonds.
The article ends with a provoking sentence: "Apollo and others should rue that they did not demand equity warrants". If you are wondering how much money Apollo left on the table, you are in the right spot.
Based on my math -> $4.481Bn 1) Warrants in Restructuring 2) Assumptions of the Apollo Missed Warrants 3) Apollo Implied Value Equation 4) Current Value of Warrants 5) Sensitivity and Conclusion
A Thread 🧵
1) Warrants in Restructuring
In order to understand this thread, we need to understand the basics first.
In the beautiful world of restructuring and corporate reorganization, there are times when the value of the business is not enough to cover the claims of all debt holders. As a result, companies go to their creditors asking to renegotiate their claims in order to stay alive and maximize everyone's value in the long term.
But what if the company has nothing to offer? A possible solution is issuing warrants (security that gives the holder the right to buy or sell a specific number of shares of a company at a specific price, called the strike price before the warrant expires).
Let's say a company is trying to create a fair and equitable plan for all creditors, but the second lien creditors demand more. The issue is that there is no more debt capacity or equity to give. A possible solution is giving them (completely made-up numbers) " five-year new warrants issued to second lien lenders which would entitle them to purchase up to 12.5% of reorganized equity at a strike price equal to the value of reorganized equity".
We therefore now understand what the sentence "Apollo and others should rue that they did not demand equity warrants" is trying to tell us: Apollo wished they had negotiated some of these warrants, something that often happens in restructuring situations.
2) Assumptions of Missed Warrants
We now understand the dynamics, but why is missing out on the warrants so tragic here? Because the stock price has increased over 10x since the deal was signed so a lot of money could have been made.
How much money? Let's try to figure it out.
We need to make a few key assumptions here. Firstly, how much Carvana equity Apollo could have demanded? I believe 10% is a fair assumption (in the next tweet and the last one will show why I think this is a fair assumption).
Once we agree on how many warrants as % Total to issue, the next step is to calculate how many warrants are issued which we can calculate as Share Count * % Equity Issued = 21MM Warrants
The next key question to calculate profit would be to know the strike price of these contracts. This is the second key assumption we need to make (here I could be very wrong). It is hard to get a sense as most of the figures we know are from in-court situations while here we are out-of-court and therefore the equity is still fluctuating in value every day (differently from the example above "strike price equal to the value of reorganized equity").
I would doubt that Carvana would have ever given out warrants without premium (which would essentially mean diluting the equity by 10% right away).
For our calculation, let's use a 50% premium. Again, this might be wrong, but as the sensitivity analysis will show us, this assumption does not really matter. More on this later.
The last thing we need to understand is the price this premium will be applied to. This is usually not tricky but here we are in a unique scenario as the stock was seeing huge volatility.
The deal was announced on July 19, 2023 so for our calculation I took the last 90 days' average which comes out to $18.1 / share.
Putting these two things together, we can calculate the strike of the warrants = $27.2
Please note: the above assumptions are (obviously) solely my own.
3) Apollo Implied Value Equation
Before moving to calculate the value of the warrants today, I thought it would be useful to sense-check if we are on the right path (i.e. how much were these warrants worth at issuance compared to how much debt was written off).
First, we need to calculate the value of each warrant and then multiply it by how many were issued. I downloaded the beautiful Damodaran option price calculator and used the following assumptions (5 Year warrants duration, 100% implied vol for the stock, and 3% Risk Free Rate). With the stock price and strike price calculated above, I arrived at a value of $8.92 / warrant. This multiplied by the 21MM warrants issued gets $187MM of value issued.
Considering Apollo agreed to cut $1.3Bn of Debt, getting 14% of the value back through warrants seems reasonable.
Moving right along.
4) Current Value of Warrants
Let's get to the meat. How much did Apollo leave on the table?
Today, Carvana stock closed at $241. Let's assume Apollo owned these warrants and wanted to exit their position. They would have the right to buy 21MM shares at the strike price ($27.2) and then they would be able to sell them on the open market (let's assume no price impact despite a significant dilution for simplicity).
Overall, this would net $4.5Bn in Profits (remember there is no cost base here).
Yes, a lot of dollars.
5) Sensitivity and Conclusion
This is my favorite part of this analysis. We are sensitizing two assumptions, warrant premium (or strike price) and how many warrants we issuing. Three things stand out:
1) As expected, how many warrants we are issuing is really all that matters here. If you think Apollo would have never got 10% of the equity but much less, you can easily see how many dollars they left on the table (still in the billions range).
2) The warrant premium (or strike price) does not really move the needle. The stock ended up being so much higher than the strike price that the dollar impact is marginal. In general, creditors will fight for a low premium so the chances of these warrants having intrinsic value are higher.
3) This said, the higher the warrant premium at issuance, the lower the value of the warrants which makes the warrant value as % of the debt haircut lower.
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On July 11, Walgreens Boots Alliance shareholders approved a $23.7bn take-private by Sycamore Partners.
But you probably don’t even know the biggest winner in this saga so far.
It’s Warburg Pincus - who quietly walked away nearly three years earlier after one of the most successful exits in its healthcare portfolio (10x+ MOIC).
This is the story of how Warburg built and exited Summit Health, what made the deal work, and why Walgreens is still trying to make sense of it: 1) Betting on CityMD 2) Tuck-Ins and the Summit Merger 3) The Strategic Sale Process 4) VillageMD and Summit Health 5) Reality Hits and the Sycamore LBO
1) Betting on CityMD
In 2017, Warburg Pincus acquired a majority stake in CityMD, a high-growth urgent care provider in the New York metro area. At the time, the company had 68 locations across New York, New Jersey, and Washington, was generating roughly $240mm in revenue, and had under $40mm in EBITDA. The deal valued CityMD at $596mm, implying a 2.48x EV/revenue multiple and ~15x EV/EBITDA.
Though Warburg wasn’t actively targeting urgent care, it was drawn to CityMD’s aftercare referral model and dense urban footprint. TJ Carella, head of healthcare at Warburg, later said the company was impressed with how CityMD integrated episodic care into the broader healthcare system. The investment is part of a broader trend occurring in PE; by 2024, nearly 17% of urgent care clinics were PE-backed according to the Journal of Urgent Care Medicine.
Warburg had already invested more than $10bn in healthcare by that time, in companies like Alignment Healthcare, Coventry Health Care, and Humana. CityMD was another bet - but one that would evolve significantly.
2) Tuck-Ins and the Summit Merger
Over the next five years, Warburg transformed CityMD into a much broader platform, investing over $500mm. The firm completed more than ten acquisitions, bringing in urgent care chains, specialty physician practices, and outpatient facilities.
These included FirstMed Urgent Care, STAT Urgent Care, Franklin Immediate, Urgent Care Now, Active Orthopedics, Gotham Gastroenterology, Westmed Medical Group, New Jersey Urology, Long Island Medical Associates, and North Shore Cardiac Imaging.
The most transformative move came in August 2019 when CityMD merged with Summit Medical Group, a large multi-specialty practice. The deal occurred during the pandemic, adding operational complexity.
“Integrating those companies in the middle of COVID was a challenge as we were taking two different cultures,” Carella told Buyouts Insider.
The result was a combined organization with 1,400 providers, more than 6,400 employees, and nearly 200 locations. The strategy reflected a broader shift in healthcare toward care integration. UnitedHealth’s Optum had already acquired MedExpress and added surgical centers and physician groups.
CVS, after acquiring Aetna, announced plans to roll out care centers across thousands of stores. Warburg’s build-out of CityMD-Summit fit the same mold - only faster.
The goal wasn’t just to scale urgent care; it was to create a fully integrated outpatient ecosystem spanning primary, urgent, and specialty care.
A structure that is just arising in the restructuring / credit world is the triple-dip.
At the most basic level, the point of a triple-dip is simply to take a double dip, and determine if there is another claim that can allow a creditors claim to reach three times the book value of debt.
The case of Spirit Airlines, which we dive in our deep dive, is the first iteration of this mechanic and evidence that triple-dips can be created if the correct verbiage exists in credit documents.
For Spirit, a third dip was created via Termination Damages, as the bond indenture included a clause specifying the cost of damages owed to bondholders if the brand IP licensing agreement is terminated.
The other two dips came from the sources above: the ParentCo guarantee and an intercompany loan.
That does pose the question: what are some other ways a triple-dip could be created.
Although it is always going to depend on the credit doc, corporate structure, and what creditors are allowed to do, below are some possible ways that I have thought a triple-dip could be created:
This is the most natural extension of a double dip
As a reminder, in a double-dip, we gain two claims from an intercompany loan and a guarantee.
Although it may seem simple to create a new subsidiary and provide another intercompany loan, for example, to get a third claim, this would not actually provide a triple-dip as this new intercompany loan still requires capital from a creditor group.
Thus, to create a triple-dip ‘naturally’, we need to maneuver the existing capital around the corporate structure to gain an additional guarantee secured by the same pool of assets.
Reference figure below for an example to demonstrate this idea.
While this diagram may look complicated, it is simply an extension of the double-dip seen.
In this example, we have $400mm of Secured Notes being issued to SubCo Y. As in a standard double-dip, we have our first claim coming from an intercompany loan to the ParentCo.
Our second dip comes from the guarantee from the restricted subsidiary on the $400mm debt issued by the triple-dip creditors. Now, to create the third dip, we need to gain an additional claim (outside of the credit box).
To do so, one method could be to transfer the debt held at ParentCo to SubCo X via an intercompany loan.
The debt held at SubCo X can then be guaranteed again by the Restricted Sub, creating a third claim. In order to move assets in and out of the credit box like the example above, there needs to be a lot of credit doc flexibility.
A company could use swaps, options, and other derivative instruments between subsidiaries to create a third claim.
Like the intercompany loan, a derivative instrument represents a contract between two parties, and if structured appropriately, it could represent additional recoveries for the triple-dip lenders.
Figure #4 below depicts how this structure could arise.
As it was in Figure #3, there is a first claim from the $400mm intercompany loan, and a second claim from the $400mm restricted company guarantee.
However, the third claim is created via an interest swap contract entered into between SubCo X and ParentCo (using the $400mm upstreamed from SubCo Y).
To briefly explain how swap contracts work, it is an agreement between two parties to exchange their interest payments for one another over a set period of time. Let’s say that we have a mortgage of $1,000,000, with a 10% fixed interest rate. If we believe that interest rates are going to be lower than this rate over the duration of a swap contract, an individual can engage in a swap contract with a bank.
To do so, they would swap their 10% fixed interest rate for a rate that the bank provides, say SOFR + 2%. If the contract lasted 5 years, each year the bank would have to pay the 10% rate and the individual would only have to pay the SOFR + 2%.
In our example swap contract, we can assume that it has a notional value of $400mm, where SubCo2 pays a fixed rate (i.e 5%), and ParentCo pays a floating rate (i.e SOFR+3%).
If, at the time of the filing, the present value of the swap contract is positive to the benefit of SubCo X, it becomes an additional claim. Thus, if that swap contract reached a present value of $400mm, a third claim could be created.
Life insurance is reshaping credit markets and its impact on restructuring will be game-changing.
Remember when the most dramatic part of a restructuring was a fight over Debtor-In-Possession
(DIP) pricing or a heated meeting about covenants? Well, today, the real drama happens inside the
balance sheets of Megafunds.
Here’s what you need to know about how insurance-backed capital is becoming Megafunds’ quiet force steering distressed deals and how Apollo, KKR, and Brookfield specifically are turning life insurance into a secret weapon 1) Insurance 101 2) Why you should care 3) Apollo x Athene 4) KKR x Global Atlantic 5) Brookfield x American National 6) The Forced-Sale Trigger 7) Bottom Line
Insurance 101
Life insurers aren’t piling into credit because they’ve suddenly discovered their inner hedge-fund
manager. They’re doing it because they’ve promised policyholders a fixed annuity check every
month until 2055.
To keep their promise, they need medium-yield assets that can securely hum along for decades. Enter distressed loans, structured credit, and even DIP financings
In short, life insurance liabilities = very long-dated bonds.
When a client buys an annuity, the insurer
is on the hook for payments 10-50 years out.
The present value of those obligations is discounted
using interest-rate curves, and if rates fall, the liability’s value jumps, and regulators demand more
capital padding.
Asset-liability matching is the name of the game here. Life insurance companies are less worried about beating the S&P and more worried about simply making sure assets and liabilities stay in sync.
If an insurer can achieve a predictable 6-8% over 30 years instead of pulling a Structured Alpha 2.0
their CIO will keep their job.
Why You Should Care (Implications on DD and RX)
Here are some ways insurance capital disrupts the script on everyday DD and RX.
A Change in Negotiation Leverage
- Remember that these life insurers are LONG term, so any marginal price breaks that make for a strong IRR over 5 years barely show up for an insurer that plans to sit on the asset for 40 years (basically, since insurers are aiming for decades of coupon flow instead of a quick flip, they’re willing to pay closer to par for discounted debt to outbid other funds.)
A Different DIP Pricing Strategy
- Although insurers may require stricter covenants to decrease risk on DIP financings, their patient investment approach means they can afford to offer lower coupon rates than most other investors. If insurers accept 6% DIP spreads, your distressed hedge fund expecting 12% is out of luck
Secondary-Market Valuation Problems
- Because insurers often buy debt to hold for long periods, the market could go quiet, meaning with no recent quotes, it becomes harder to model what the debt is worth.
Below are the poster children for this “insurance eats credit” trend. Each combines a global alternative asset manager with an insurer that produces gigantic but predictable cash inflows.
Private Wealth is the next big source of capital in private markets.
This is Kipp deVeer. He is the Co-President of Ares, and in his most recent interview with Capital Allocators, he discusses Ares’ focus on the source of capital of the future: private wealth.
Kipp notes that the mass affluent of high-net-worth individuals (HNWI) have a growing desire for more sophisticated portfolios beyond the traditional 60/40 allocation, following negative returns in the early 2020s. With the growing prevalence of alternatives, private wealth managers view the sector as a substitute.
A decade ago, the channel was mostly limited to non-traded REITs, with Blackstone holding 60% of the market share. Since then, product innovation has widened offerings, from secondaries funds to private credit strategies. ‘40-Act wrappers have underpinned this shift and are the vehicles that allow HNWIs to enter the less-liquid markets. Two key examples of ‘40 Act wrappers within the private credit space include Business Development Companies (BDCs) and Interval Funds:
1. Business Development Company - Listed or non-traded, a BDC pools private credit assets, and like REITs, passes most of the investment income through dividends [2]. BDCs dominate debt-focused ‘40 Act funds, holding roughly $340bn of the $400bn segment [3].
2. Interval Funds - These funds offer “semi-liquidity,” allowing redemptions only at scheduled monthly or quarterly intervals. This illiquidity allows managers to own harder-to-trade assets, such as alternatives or private credit, without daily pressure [4]. Interval Funds now account for about $50bn of the debt-focused ‘40 Act funds.
Market share is heavily concentrated, with just four or five mega-funds, such as Ares, Blue Owl, and Blackstone, controlling over a third of the private wealth channel. The expansion of private wealth extends beyond more stable asset classes like private equity or credit, but also to VC. Benchmark’s Bill Gurley remarked in a recent podcast that Coatue is also exploring an interval fund, allowing HNWIs to delve into the space.
2) Ares Approach
Ares began to enter the private wealth market about 6 years ago with its acquisition of Black Creek Group, a 75-person real estate platform led by former Morgan Stanley banker Raj Dhanda [5]. Although hesitant initially, with a push from Raj, the firm realized that they needed to “race to the finish line.”
Ares began its scaling effort by sending senior partners—not just junior salespeople—to major wirehouses such as Morgan Stanley and Merrill Lynch, creating deep-rooted relationships that now anchor its wealth-channel strategy.
Kipp argues that Blackstone’s early dominance created an opening for Ares, as many advisors and wirehouses sought strong private-market products without concentrating client assets in a single manager. Instead of overwhelming financial advisors with a maze of products, Ares keeps its private-wealth portfolios curated to a total of six or seven areas that currently span credit, real estate, private equity, and infrastructure. The firm organizes these portfolios across three core themes:
1. Durable Income - Ares has built its brand on private credit, pitching it to advisors as steadier and less volatile than public credit while delivering premium returns. This approach has resonated with the private wealth community: the firm’s retail credit funds are both its largest and fastest growing, as investors “set it and forget it,” as Kipp described.
2. Diversified Equity - Kipp observes that wealth-focused firms are tackling private equity through both traditional primary-oriented funds and secondaries, but Ares seems to have joined the latter. Raj Dhanda argues that “over time, secondaries will be the preferred method of investment” because they deliver broad diversification without giving up returns [6]. This thesis is reflected in Ares Private Markets Fund’s (APMF) 96% allocation to secondary investments.
3. Tax-Advantaged Real Assets - Ares covers tax-efficient real assets through traditional REITs and has been expanding its presence in infrastructure. The recent purchase of GCP International underscores this focus, expanding Ares’ exposure to digital infrastructure across the globe.
The model is working and scaling quickly. Approximately $40bn of Ares, roughly $500bn AUM, already originates in the wealth channel. While most similar firms forecast as much as 40% of future fundraising to come from private wealth, Kipp expects Ares to raise closer to 20% of 2025 capital from retail channels, still a significant chunk.
By keeping the lineup simple, Ares aims to convince financial advisors that every dollar placed in an Ares fund carries the same downside control and information edge that its institutional LPs have relied on for decades.
🚨 Private credit helped build a boom. Now it’s creating a mess.
Distress is spiking across the middle market, but not the kind we’re used to…
More firms are failing by accident than by design. And many lenders? They’re learning workouts in real time.
SCP CEO Lawrence Perkins breaks it all down on Bloomberg’s FICC Focus.
Here are my insights that every operator, sponsor, and creditor should know 🧵
1) Rise of “Distressed-by-Accident” Cases
Perkins observes a growing cohort of workouts he calls “distressed by accident." These are situations where overly aggressive financing (often from private lenders) unintentionally pushes a company into trouble, rather than a planned restructuring.
In his words, he’s seeing “more ‘distressed by accident’ lenders these days, courtesy of the private credit boom, than the ‘distressed on purpose’ ilk.” For restructuring professionals, the implication is clear: sponsors and advisors must monitor covenant-heavy deals closely.
Even healthy companies can suddenly trigger defaults, so early warning signs must prompt prompt action. In practice, this means conducting stress tests and engaging lenders before a crisis spirals out of control.
The interview highlights how the private-credit boom has reshaped the distressed-debt landscape. Perkins directly links the “distressed by accident” trend to this boom.
With more non-bank lenders and direct-credit funds in the market, mid-market companies have taken on debt structures that may not have been fully tested in downturns.
These lenders often lack formal workout experience or coordination mechanisms (such as lender committees), so their deals can catch all parties by surprise.
The net effect is a broader, more unpredictable distressed market. Sponsors and buyers must now navigate a crowded field of creditors—many with new playbooks—and may face rapid-fire collateral sales or consent solicitations.
Perkins’s insight suggests that distressed professionals must adapt: anticipate a higher volume of unexpected workouts and be ready to educate these new lenders on restructuring processes.