First – I have to direct you to http://www.angelikalanger.com/GenericsFAQ/JavaGenericsFAQ.html — she does an amazing job.
The basic idea is that you use
<T extends SomeClass>
when the actual parameter can be SomeClass or any subtype of it.
In your example,
Map<String, Class<? extends Serializable>> expected = null;
Map<String, Class<java.util.Date>> result = null;
assertThat(result, is(expected));
You’re saying that expected can contain Class objects that represent any class that implements Serializable. Your result map says it can only hold Date class objects.
When you pass in result, you’re setting T to exactly Map of String to Date class objects, which doesn’t match Map of String to anything that’s Serializable.
One thing to check — are you sure you want Class<Date> and not Date? A map of String to Class<Date> doesn’t sound terribly useful in general (all it can hold is Date.class as values rather than instances of Date)
As for genericizing assertThat, the idea is that the method can ensure that a Matcher that fits the result type is passed in.