I own one and I can confidently say no, if paying full retail. I bought mine on Craigslist for about half retail. Cheaper than I could get a new Engel or K2. Does he need or even want an "extreme" cooler? Depends on what he is going to use it for, IMO. You don't want to carry them around like you would a $10 igloo. Too heavy. Made the mistake once of carrying it to the beach.
Don't get me wrong. I like mine, but it has a specific use. I travel 3-5 days a week for work (averaging 1,000-1,500 miles). I load it up when I leave so that I don't have to pay for water, drinks, etc at a gas station. A cooler takes up too much room in my back seat, so it stays in the truck bed secured with a locking cable to keep it from walking off. Any cooler is going to act the same when you fill it with ice and drinks. Heat transfer is going to occur to bring the ice, drinks, and air to the same temperature (plus the inefficiency of the cooler). I've heard if you want your ice to last longer, freeze some water jugs and put them in the cooler 24 hours before but never tried it. I usually raid the ice bin in the fridge to piss off the wife and then refill at the hotel for free.
You did mention that he was a Bear. Buy the Yeti. It will match his red pants, blue shirt, and pink bow tie. And he won't be ashamed to bring it to the tailgate. I suggest getting him a sticker that will differentiate his Yeti from his friends' Yeti similar to how you tag your luggage at the airport with a unique identifier. He will need the following stickers to fit in: costa, John Deere, cotton, Rebel battle flag, salt life, PBR, vineyard vines, southern marsh, ducks unlimited, browning, drake, under armour, etc.