Here’s a good way to create a true memory leak (objects inaccessible by running code but still stored in memory) in pure Java:

1. The application creates a long-running thread (or use a thread pool to leak even faster).
2. The thread loads a class via an (optionally custom) ClassLoader.
3. The class allocates a large chunk of memory (e.g. new byte[1000000]), stores a strong reference to it in a static field, and then stores a reference to itself in a ThreadLocal. Allocating the extra memory is optional (leaking the class instance is enough), but it will make the leak work that much faster.
4. The application clears all references to the custom class or the ClassLoader it was loaded from.
5. Repeat.

Due to the way ThreadLocal is implemented in Oracle’s JDK, this creates a memory leak:

• Each Thread has a private field threadLocals, which actually stores the thread-local values.
• Each key in this map is a weak reference to a ThreadLocal object, so after that ThreadLocal object is garbage-collected, its entry is removed from the map.
• But each value is a strong reference, so when a value (directly or indirectly) points to the ThreadLocal object that is its key, that object will neither be garbage-collected nor removed from the map as long as the thread lives.

In this example, the chain of strong references looks like this:

Thread object → threadLocals map → instance of example class → example class → static ThreadLocal field → ThreadLocal object.

(The ClassLoader doesn’t really play a role in creating the leak, it just makes the leak worse because of this additional reference chain: example class → ClassLoader → all the classes it has loaded. It was even worse in many JVM implementations, especially prior to Java 7, because classes and ClassLoaders were allocated straight into permgen and were never garbage-collected at all.)

A variation on this pattern is why application containers (like Tomcat) can leak memory like a sieve if you frequently redeploy applications which happen to use ThreadLocals that in some way point back to themselves. This can happen for a number of subtle reasons and is often hard to debug and/or fix.