It's the max speed it can do out of the box - not necessarily on stock cooling. A i9-9900K has a max turbo of 5GHz, but does not ship with a stock cooler.
Typically, there are different levels of "max turbo". The one specified is usually single-core only though, and the "max" is lower the more cores you load up.
Using the 9900K again, the max turbo is 5GHz on 2 cores, 4.8GHz on 4, and 4.7GHz on all 8.
https://en.wikichip.org/wiki/intel/core_i9/i9-9900k
Overclocking results are never guaranteed, and would never be stated as a "max" in any marketing. Yes, you certainly have a chance of OCing a chip beyond the max turbo listed, provided thermal/voltage headroom etc.
An "overclock" on a 9900K would be something as simple (sounding) as 5GHz all-cores, as it's above the stock, out of the box operation.