Age of Empires II: Definitive Edition (PC) - Achievement - A Second Hastings
Wipe out Humphrey's base before defeating Jacqueline in "The Hook and Cod Wars".
To win, you must destroy Jacqueline's castles in the 3 cities she has. Humphrey (Red) is based across the sea from your starting camp and will annoy you with boat attacks and the occasional troop landing. He must be eliminated before you destroy Jacqueline's 3 castles for the achievement to trigger.
Humphrey is based all along the coast which means you can use Cannon Galleons to destroy a good chunk of his buildings, but you are still left with two castles and his inner, less coastal buildings to deal with. Also note that there is an objective to destroy his 3 Lumber Camps which can be destroyed with Cannon Galleons. Once you do this, he will no longer build boats, however the achievement states you must WIPE OUT Humphrey's base, so destroying the Lumber Camps alone is not good enough. You have to destroy him completely / force him to retire.
Your best bet is to clear a landing area with Cannon Galleons and build a forward base on his land. He can be a bit tedious to deal with as he focuses on Longbowmen which are quite effective against Bombard Cannons, so Capped Rams are a good alternative siege weapon to use. Due to his Longbowmen being close to his castles, it's not always easy to just counter them with cavalry either as the castles will kill them pretty quickly. He will also construct siege weapons to counter you building on his land.
Once you eliminate Humphrey, return focus to Jacqueline and finish the level, triggering the achievement. Note that once you destroy one of Jacqueline's castles, you take control of the buildings left in the city. One of Jacqueline's castles can be destroyed using Cannon Galleons as it is fairly close to the sea.