July 24, 2025
As someone who's spent years in the trenches analyzing covenant packages and watching borrowers execute increasingly sophisticated liability management exercises (LMEs), I wanted to share some critical insights from our recent webinar on this essential topic. If you missed the live session, don't worry – the replay is available and packed with actionable frameworks you can use immediately.
Let me be direct: incumbent flexibility is at an all-time high. Borrowers have more options than ever, and lenders are scrambling to provide opportunistic solutions. The best defense? Understanding exactly what's possible under your covenant package before it happens to you.
I've seen too many lenders caught off guard because they didn't fully grasp the flexibility buried in their own documents. As I always tell my students: the best offense is a good defense. You need to know what provisions are lurking in your deals, where to find them, and how to analyze them effectively.
Before diving into specific LME structures, you absolutely must understand the four types of subordination. Master these concepts, and you're more than halfway through any covenant analysis:
These aren't just academic concepts – they're practical tools that help you understand what's actually possible in any deal structure.
In the webinar, I walked through several high-profile cases that showcase different LME strategies:
J.Crew's Unrestricted Subsidiary Play taught us about asset drop-downs and the importance of understanding your investment capacity limitations. The key insight? You can aggregate builder basket, permitted payments, and permitted investments capacity – most people miss this.
Serta's Up-Tier Transaction showed how majority lenders can create new senior debt positions, leaving minority lenders subordinated. The lesson: check your required lender thresholds and open market purchase provisions carefully.
Pet smart's Non-Wholly Owned Guarantor Strategy demonstrated how guarantee releases can happen automatically when ownership drops below 100%– and this flexibility exists in most loan agreements.
At Home's Double Dip illustrated how borrowers can give new lenders two separate recovery paths, effectively creating multiple bites at the apple.
Here's the systematic approach I use for every covenant analysis:
The reality is that many of these structures exploit flexibility that's been standard in documentation for years. The key is knowing how to limit exposure:
Whether you're representing borrowers, lenders, or financial advisors, understanding these concepts isn't optional anymore. I've watched too many transactions where one side had a significant advantage simply because they better understood the covenant mechanics at play.
The borrowers executing these transactions aren't necessarily the most distressed – they're often the most sophisticated. They understand that these LMEs can extend runway, but the real question is: at what cost to ongoing operations and stakeholder value?
This blog only scratches the surface of what we covered in the full webinar. The replay includes detailed transaction diagrams, specific covenant language examples, and additional defensive strategies that didn't make it into this summary.
The financial markets continue to evolve, and covenant sophistication is accelerating. Whether you're analyzing a potential investment, defending an existing position, or structuring new transactions, having this analytical framework in your toolkit is essential.
Watch the full webinar replay here to get the complete analysis framework, see the detailed case studies, and access the specific covenant language examples we discussed.
Remember: in the world of leveraged finance, knowledge truly is power. The question is whether you'll have it before you need it.