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In Emerald, those evil twins with their obviously hacked pokemon. KO'd all my pokemon except Aggron, who got really lucky to come on the Solrock and Lunatomb so worry about Earthquake and making critical hits.
Tate and Liza's entire gym practically went through holocaust when I got there.
Norman fell with ease against my Machoke. (Just a worker Pokemon my a...anyway.)
But Watson...oh the horror...no more shock waves...please...
Norman was nearly impossible in my first Sapphire run, but since I always have come prepared to take him on. Still a heck of a fight. His bigger Slaking is evil - the rest of his Pokemon not so much. I just need to have a Breloom, Machoke, or Blaziken in stock.
Tate & Liza are also REALLY REALLY hard, and are probably my current answer. They're definitely hackers, lol.
I always found Norman to be quite a challenge as well as Tate and Liza. I never could surpass Norman's Slaking's power and it really irritated me when it would usually one hit KO me. ):
In the older days of Sapphire, I used to dread Wattson because I would always have a Grovyle. I remember a particularly horrible experience when I had a Grovyle, Crobat (it evolved 2 levels after Golbat :D), Pelipper, Beautifly, and Aron. It was that day that I sweared revenge against Wattson >:( But I found out about Tate & Liz.... Even with type advantage, I somehow lost at least 6 times...
I'd definitely say Tate and Liza. I had enormous trouble on my first run so many years ago with a level 65 Sceptile and a level 40 Mightyena even. But back then I didn't even know about type advantages, and 4 of my 6 Pokemon were all like level 15 (I was lazy -_-)
None, really. Mudkip- Marshtomp- Swampert essentially took care of all of the gyms up to Wallace/ Juan and even then, Shiftry took care of that. If I had to choose though, I guess Norman and his Slaking posed the most challenge to me.
Particularly, Norman as well as Tate and Lisa gave me a really hard time in my first play through as their Pokemon to me were extremely hard to beat. Though, this was also the first time I had ever played through a Pokemon game so, that may have also played a factor, but Lunatone and Solrock were a hard duo to beat.
I am gonna have to say Norman. When I played RSE I did not really pay attention the weaknesses. Now,I don't think I would have that big of a problem. But it has been forever sense I played RSE.
Liza & Tate weren't so hard for me.A couple of Surfs and its over.The most trouble i had is with Wallace because i didn't have a good type advantage against him.
I don't remember who I have the hardest time with on Ruby. My bets would have to go with Norman because back then my teams never had a Fighting type nor a Fighting move. But on my Emerald I would have to say Juan because Kingdra and being quite under leveled. Also Girafarig being the one with a Thunderbolt move ye-up. Not sure if I had my vileplume by then either.
Mine was for some odd reason Tate and Liza. During my first time playing but I was like 8 or 9 and it was my first pokemon game so yeah. In my replay it was Norman but I only failed 2 or 3 times.
~Sincerely
PikakittenX, devout member of the Pokecommunity
Of all the regions, Hoenn has by far the hardest gym fights. But the hardest is, fittingly, Juan. His team is filled with attack based Pokemon. His Kingdra is insane too, and loves to spam double team.
(Am I the only one who thought that Tate & Liza weren't that hard?)
Tate & Liza were never easy for me, because all of my teams consisted of Blaziken and Swellow, who sucked in the gym, and I usually had some poison type, which always left me to have to try beat them with mainly my water type.