Leases are meant to make things clear. They are meant to set limits, make sure people do what they’re supposed to, and make things more predictable in a relationship that might otherwise feel unsure. In New York, though, upholding a lease often shows how fragile those promises can be. What seems solid in writing can fall apart in court, and what seems simple to a landlord can quickly turn into a long, expensive, and uncertain fight.
For property owners, the challenge is rarely a lack of contract language. It is the gap between what a lease says and how courts interpret it, how tenants respond to it, and how procedural rules shape the outcome. Lease enforcement is not simply about pointing to a clause; it is about anticipating the obstacles that will emerge once that clause is tested in Housing Court or Supreme Court.
Few practitioners know this terrain better than Nativ Winiarsky, a partner at Kucker Marino Winiarsky & Bittens LLP. He has been a lawyer for landlords and tenants in New York for years and has seen how even the best leases can fail if they are not enforced properly. He thinks that property owners should stop seeing leases as set in stone and start seeing execution as a discipline, where planning, accuracy, and strategy are just as important as the lease itself.
Ambiguous Drafting
When people try to enforce a lease, the most common problem starts before the ink is dry: there is confusion. Clauses that make sense during negotiations may not make sense when looked at closely by the law. Words like “reasonable,” “customary,” and “timely” sound useful but can mean different things to different people. In court cases, reasoning usually works in favor of the tenant.
Nativ Winiarsky stresses that landlords must draft with litigation in mind, not just negotiation. Every clause should anticipate dispute: How will it be enforced? How will a court read it? What defenses might a tenant raise? Failing to build this foresight into drafting leaves landlords exposed when enforcement becomes necessary.
Procedural Missteps
Even the strongest lease can be undermined by procedural error. Notices served incorrectly, deadlines missed, or filings submitted in the wrong forum can render enforcement efforts ineffective. In a system where tenants often have access to procedural defenses, these mistakes can delay or derail a case entirely.
According to Nativ Winiarsky, landlords frequently underestimate the importance of process. The Housing Court is very strict when the law’s standards are not followed exactly. One weakness that keeps coming up is service of notice. A owner who thinks “close enough” is enough will often have the whole case thrown out, which means they have to start over.
Overlooking Tenant Defenses
Enforcing a lease is not done in a minute and nor is it as simple. Tenants have many defenses they can use, especially in New York. These range from claims of “warranty of habitability” to claims that the owner was not following the rules. Even if these defenses aren’t very strong, they can make the case take longer and cost more.
Nativ Winiarsky points out that landlords who fail to anticipate these defenses are forced into reactive positions. Being prepared is very important. Assume that every enforcement action will be met with counterclaims or defenses, and plan your legal strategy to deal with them ahead of time.
Poor Documentation
The most important thing for compliance is documentation. Without clear records of communication, performance by tenants, and compliance by landlords, judges are left with different stories. When landlords can’t back up their claims with proof, judges don’t want to strictly enforce leases
For Nativ Winiarsky, the message is simple: landlords must treat documentation as a daily discipline, not a task to be completed only when disputes arise. Repair logs, payment histories, and correspondence should always be maintained in a way that it’s clear and available when needed. In litigation, documentation often determines credibility and that determines the final outcome.
Misjudging the Value of Settlement
As a matter of principle, landlords sometimes uphold leases and won’t even consider settlement, even if it would be better for business. There are times when it’s right to be firm, but refusing to negotiate can make a disagreement last longer than it needs to and add more risk.
Nativ Winiarsky cautions against viewing settlement as weakness. The decision to settle should be based on strategy and a cost-benefit study. Settlement can often save money, keep relationships between tenants strong, and keep people out of court for a long time. The mistake is not refusing to settle, but not figuring out when it makes sense to settle
The Path Forward: Strategic Enforcement
Avoiding these pitfalls requires more than caution. It needs strategy. Landlords need to be as smart about enforcing leases as they are about making decisions about financing, growth, or investments. That means careful writing, organized paperwork, following the rules exactly, planning for possible defenses, and making sure the work fits with bigger business goals.
For Nativ Winiarsky, the most successful property owners are those who view litigation not as an interruption to their business but as an integral part of managing it. They plan for disputes, prepare for challenges, and approach enforcement as one of many tools in preserving property value.
In the end, a lease is only as strong as the landlord’s ability to enforce it. And in a city as complex as New York, enforcement is never just about clauses on a page, it is about navigating law, process, and strategy with precision.
