In fact, no console who was the strongest on the market ever won a console generation before the PS4, totally negating his argument:
2nd Gen Atari 2600 won, Atari 5200, Colecovision and the Intellivison were more powerful
3rd Gen: NES won, Master System and PC Engine were more powerful
4th Gen: SNES won, NEo-Geo and SupergraphX were more powerful
5th Gen: PSOne won, N64 was more powerful
6th Gen: PS2 won, Xbox and Gamecube were more powerful
7th gen: Wii won, PS3 and Xbox 360 were more powerful
8th gen: PS4 won, and was also the most powerful unless you want to count the One X
2nd Gen Atari 2600 was released in 1977. Atari 5200 and Colecovision were released 5 years later (one year before the market crash). The only console in your list released "only" one year later was the Intellvision, and when you notice that the console was 50% more expensive (and 300 bucks in 1978 was REALLY expensive for a gadget), you can understand the result easily.
3rd gen Nes Was released in 2983 (so this 3rds gen console was a competitor of some of the 2nd gen consoles, go wonder why they failed so hard) while the Master System was released in 1985. But ok, let's accept that as a "win" for the weaker console.
4rd: Are you kidding us? In the 90s, we wanted a Neo-Geo. But the price was WAYYYYYYY to high. More than 3 times the price of a Super Nes and let's not even talk about the price of the games. At this point, they are not even in direct competition. For the SupergraphX, the price was also too high, and you had to buy several add-ons too. At this point, you could be explaining why a DS "won" against a PS3/Wii/X360.
5th: PS1 was released in 1994, 2 years before the Nintendo 64. But the consoles are so different (CD vs cartridge) and you don't even take that into account for the "power". What's more powerful, a Formula 1 or a Boeing 747?
6th: at least now the consoles are similar enough for the comparaison to make sense (at least for Xbox and PS2, the Gamecub was still an oddity). Again Microsoft released their console late and their marketting was already a disaster. But the PS2 was also marketted as a DVD reader, while the XBox required an external IR adapter. But ok, let's take it as a win.
7th: at least now we can talk. Yeah the Wii was the least powerful console, the prices were not so different and there wasn't an additionnal "bonus" (like a DVD player).
8th: if you start to bring the iteration launch really late ....
So yeah, if you release your console one year before the next gen AND are in direct competition with this new gen, you won't win the generation. Yeah, if your console is 3 times more expensive, you won't win the generation. Yeah, if your console lacks basic features, you won't win the generation. And we can add the marketting failure from Microsoft, when will they learn that a console is primary sold for, you know, playing games?
Oh, on a general topic note and the launch of the new Xbox is a failure, at least in Japan (nobody wants that console, and please moderators, this is a fact from the charts: 382 consoles sold in a week is a disaster) and Europe (there isn't much supply issue for the Series S and outsold by the PS4). The console is already behind the PS5 in the US, unlexx they can find some exclusives to make people buy their console, the ratio PS5/Xbox Series will be higher than the PS/XOne=2.33. The current ratio PS5/Xbox Series is already at 1.89 and the PS5 has huge supply issues.