I don't necessarily think this was a problem in itself - but giving him his own solo show absolutely was a sign that they didn't understand what Jack's appeal is in RLM. Pairing him with Yahtzee is... is retarded. I can't think why a content manager would ever think that was a good idea, except for complete obliviousness.
Jack is a neutral tone. He's never particularly funny, but he's rarely offensive, and he rarely talks over his co-hosts. (At least, after he quit Mr Booze.) The main appeal of Jack is to offset wacky, energetic, eccentric, larger-than-life characters and ground them; he's a garnish, not a main course. Ben Croshaw is not a larger-than-life character. In streams, he's often quiet, brooding, and rarely talkative unless he has a soapbox. Jack cannot serve as his opposite, because Jack is more lively and engaging in person -- it's the exact wrong formula for Jack.
I was never particularly a fan of Pre-rec because I think the magic of RLM is in the editing, but the whole reason that show has its fans is because Jack is a good pairing with Rich, and the two have a natural chemistry: Jack is orthodox, Rich is flippant, etc. Jack's Escapist Escapades have been him trying to carry shows on his back because he genuinely is more charismatic than the rest of the Escapist cast... but he's just not the kind of personality who can really headline a show.
