First up, I have to acknowledge a correction from Part 5 of the series: I completely forgot about Marill’s white belly while drawing it. I’m not even sure how that happened because I had a reference picture (several, in fact) while I was drawing it. So…I guess this is a sign of early-onset dementia?
Regardless, we left off last time after downing the Red Gyarados, which kicks off the Rocket Hideout questline. I typically handle the Rockets first for 2 reasons.

The first of which is that I value having early access to the EXP Share. It makes onboarding new team members a lot easier, especially since the overwhelming majority of wild Pokémon in Silver appear at, or below level 20. As such, it’s nice to have a way to bring them up to speed that’s far less tedious than switch training.
Plus, in this specific instance, we can throw it onto Pinellopi who has fallen quite far behind the rest of the party.
And yes – I hadn’t forgotten about Pinellopi. She just…doesn’t really have anything to do. Honestly, I could’ve waited until now to catch her given how little I’ve used her. Heck, it might’ve ensured that my team had evolved before that disastrous fight with Kevin in the Burnt Tower, which might’ve helped to even the odds.
The second reason why I typically tackle the Rockets first is pacing. I find the game feels a little more rushed, and bloated when you do the Rocket Hideout followed immediately by the siege of Goldenrod City. The Rockets tend to carry a lot of the same 3 Pokémon, so fighting them isn’t exactly the most exciting thing in the world. As such, it’s nice to have a bit of a break wherein you can fight other Pokémon for a stretch before you return to Goldenrod to finish off the Rockets for good.
That said, we do need to keep an eye on our team’s levels throughout this stretch of the game because the level cap is a little funky here. Technically, Chuck has the lower cap at 30, but Pryce’s cap is only 1 level higher at 31. There’s pretty well no clean way to handle both bosses if I actually try to match the levels of their Pokémon 1-to-1 since they’re preceded by a handful of mandatory trainer fights.
As such, we’re going to have to continue fighting the gyms with an under-leveled team. Despite this, I have confidence in our band of misfits. Outside of a few key blunders, we’ve managed quite well thus far in the challenge run, so surely we can cinch out a win against Pryce with a lower leveled team.
Famous last words, I know.
However, the team has been doing quite well ever since the majority of them managed to evolve. Though, Winston is still getting rocked, so I’m growing increasingly impatient waiting for a Moon Stone. Hopefully, I hit the cash threshold where Mother will buy it sooner rather than later because I’m unsure if Winston can keep up with the rest of the team in the meantime.
Either way, we head back to Mahogany to begin the Rocket Hideout quest, which kicks off with a bang as Lance kills a man with his Dragonite. Seriously. He commands his Dragonite to use Hyper Beam on this ruffian, which I think is the only instance of Pokémon on human violence across the entire series? If it isn’t then it’s gotta be one of the only ones where a “good guy” does it. Honestly, it’d almost have been better if he shot the guy instead. It probably would’ve hurt less.

Aggravated assault aside, Lance swiftly abandons us, which gives us the opportunity to explore the hideout at our own pace. Unfortunately, the first area of the hideout is a bit of a slog. It’s filled with hidden cameras, and the same 2 bodyguards will keep challenging you to battle every time you’re spotted. This is exactly as boring as it sounds, though it is an okay source of EXP and money, both of which our team needs.

I feel like it’s also worth noting that Vanessa, and Mabel pulled ahead of the rest of the pack during this stretch. Actually, they dominated most of the Rocket Hideout. Vanessa’s Poison typing allowed her to resist both the Poison type attacks, and Poison status condition that Rockets generally rely on to chip down your team over these protracted dungeon sequences. Furthermore, having access to Dig gave her a strong Super Effective option in most fights.
In a similar vein, Mabel’s elemental punches, and relatively high Speed stat allowed her to get the drop on every Pokémon that Vanessa couldn’t handle. As it would turn out, Flying Pokémon are a lot less frightening to Bug types that pack both an Ice, and Electric move. Who would’ve thought?
That said, I’m not too concerned about the level gap just yet. As I’ve already mentioned, this whole section of the game has a completely flat difficulty curve, so we’ll still have plenty of opportunity to train up the other half of our team while we handle the lighthouse questline. Heck, Trevor will probably have a much better time there since the bulk of that part of the game is filled with Water types that he easily trumps.
Regardless, nothing else of note happened throughout the remainder of the hideout, so I’ll skip ahead to the bit where Lance gives us Whirlpool, which opens up Pryce’s gym. It also allows us to pick up Sludge Bomb on Route 43, which I throw onto Vanessa. This is the strongest (?) move that she can learn when you account for Same Type Attack Bonus (STAB), so it’ll make a great addition to her repertoire.
Editor’s Notes: minor correction. Hyper Beam is the strongest move Arbok can learn, but it isn’t available until after the Elite Four. As such, Sludge Bomb is technically the strongest move Vanessa can learn.
With all of that out of the way, I attempted Pryce’s gym, and was swiftly hit with a reality check: my team is very weak against Ice types. Mabel, and Trevor both take Super Effective damage from Ice attacks, and Winston is too weak to contribute meaningfully to fights as a Jigglypuff. Never mind, I wasn’t even training Winston throughout the Rocket Hideout, so he’s woefully behind where he ought to be if I wanted to use him for this gym, as is Pinellopi.
That leaves us with a single option for Pryce: Vanessa.
Now, I know Vanessa has been on a bit of a redemption arc as of late, but I don’t see a world where she clears Pryce solo. I’m fairly confident that she could take out his Seel, and Dewgong with strong STAB Sludge Bombs, but there’s no way we can clear the bar against Piloswine. It only knows Ice moves, so it can’t hit us for Super Effective damage, but we can’t really deal strong damage in return. As such, I’m fairly certain we’d get outpaced. And I don’t trust that Mabel could clean up the fight before she also gets KO’d too.
That puts me in a bit of a pickle.
Frankly, this is normally where I’d want to lean on Winston since he knows both a Rock, and Fire attack, which are Super Effective against Ice types. His normal typing also works well defensively since he goes neutral to Ice just like Vanessa. However, Winston just can’t keep up with these evolved monsters. The stat difference is too great.
For a small example of what I mean: I used Winston against gym trainer Clarissa’s Dewgong. He was 2-shot by Aurora Beam, so he barely got a hit in before going down. Mabel, who takes Super Effective damage from Ice moves, could tank the same 2 Aurora Beams and score the KO. Yes – a Pokémon who took double damage from Aurora Beam was able to tank more hits simply because her stats are that much higher after evolving.

There’s no getting around it – we need that Moon Stone now. Without it, Winston is struggling to meaningfully contribute in combat, and I think we need him if we want to beat Pryce. Though, Mother clearly lacks the funds to purchase the Moon Stone on our behalf. That means we have 2 options to trigger the event that’ll cause her to purchase the stone.
Either we:
- Take a massive detour down to New Bark Town, and top her off with the difference in funds so that she’ll be forced to finally buy the Moon Stone
- We continue smashing our head into the wall with local trainers, and pray that the difference in funds is small
You know I chose the latter.

Thank God.
I’d almost forgotten about the trainers that show up to the Lake of Rage following the completion of the Rocket Hideout. Thankfully, these intrepid individuals tipped me over the edge to where my savings were large enough to obtain the Moon Stone. Now we can finally get this long overdue evolution sorted, so Winston’s extreme poverty can be a vestige of the past.

Glorious.
As predicted, evolution into Wigglytuff awarded Winston a, frankly, absurd boost to all of his stats. This made cleaning up the remaining gym trainers a cinch, so I was a lot more confident in our chances of beating Pryce than I was previously. It was now, or never.
To begin the fight with Pryce, I led Trevor. At first brush, this might seem foolish because all of Pryce’s team only knows Ice type attacks, which deal Super Effective damage to Trevor. However, Trevor can outspeed Pryce’s Seel. Weepinbell is naturally faster than Seel, and we also have the Badge Boost from Whitney’s badge for an additional 12.5% increase to our Speed stat. Ergo, we’re able to move first, and utilize the Trevor classic of putting our foes to sleep with Sleep Powder.
From here, I sent out Winston with the intention of utilizing the same strategy as I did against Whitney: Defence Curl and Rollout. The only difference here is that I’ll be attempting to sweep through Pryce’s entire team. It isn’t a terribly reliable strategy thanks to Rollout’s flakey accuracy, but it doesn’t need to be. If I can KO Pryce’s Seel, and Dewgong with Winston then I’m fairly certain that I can win. I wasn’t confident Vanessa could solo this fight, but I’m extremely confident that she can win in a 1-on-1 against Piloswine provided she starts from full health.
As such, we set up Defence Curl, and clicked the funny button. It was all in RNJesus’ hands now.
Sadly, Seel woke up on the following turn, so we ate a hit before we could take it out with a turn-2 Rollout. However, our newly obtained bulk from evolution ensured that we took minimal damage.
The same was true on the following turn when Pryce’s Dewgong landed a Critical Hit Aurora Beam. I’m almost certain that would’ve KO’d Winston if he was still a Jigglypuff. However, he’s a proper chungus now that he’s evolved, and easily ate the crit before firing off a counterattack.

Predictably, Dewgong did not survive the Super Effective, turn-3 Rollout.
In my mind, this KO meant that I’d won the battle. All I needed to do now was send Vanessa into battle after Pryce’s Piloswine took out Winston. Then I could win a 1-on-1 with a combination of Dig, Headbutt, and Sludge Bomb.
However, something unexpected happened: Winston outran Piloswine. I was certain that we would be slower, but I guess Badge Boost gave us the extra push to move first. This allowed Winston to send our foe to the Shadow Realm before Pryce got the opportunity to retaliate.
…Well, alrighty. That felt like a bit of an anticlimax, but I suppose we take those. Evidently, Badge Boost is helping me out a lot more than I originally anticipated.
Speaking of which, we have another stat boost thanks to Pryce’s badge. Both Special Attack, and Special Defence are now affected by the 12.5% boost, so we’ll have a much easier time downing foes with Mabel’s elemental punches, and Kevin’s Quilava should be less of a problem.
In addition, we also have the ability to use Whirlpool, which will give us the ability to capture our 6th, and final team member.
This is your last chance if you wanted to guess, and haven’t already figured out who it is.
Regardless, with Pryce sorted out we need to begin the lighthouse quest, and make our way over to Chuck. Winston, Vanessa, and Mabel are all pushing the level cap of 30, so we really need to deal with him as soon as we can.
That said, Trevor, and Pinellopi are both hungry for EXP since neither of them got much usage throughout the Rocket Hideout, nor in Pryce’s gym. Well…okay Trevor did do the Trevor thing of putting someone to sleep, but aside from that he’s been warming the bench for the last several hours of gameplay.
There isn’t much to say about the trek through Routes 38, and 39. The trainers here were perfectly balanced for our party members who haven’t done much since we bested Morty, so they were both able to grab several levels on our trek up to Olivine City.
We also obtained the HM for Strength in Olivine, which I taught to Pinellopi over Headbutt. Strength does slightly more damage, and there isn’t a world where Pinellopi was ever going to benefit from Headbutt’s 30% chance to flinch since she never gets to move first. Ergo, I thought the higher damaging move made more sense. Plus, we needed a Strength user to clear the gym puzzle in Cianwood.

Speaking of, this has gotta be the funniest HM related roadblock that I’ve ever seen in a Pokémon game. You just…can’t get through the back-half of Chuck’s gym without using Strength. It’d have almost been better if it were like Lt. Surge’s gym in Kanto where you need Cut (or Surf) to enter the gym. Here you’re like…halfway through, and then the game stops you to check if you randomly picked up an HM that you might’ve missed back in Olivine.
I dunno. I just think the whole thing is really funny because of how oddly designed it is. You’d think that you’d want the NPC to be in Cianwood so that if players missed the HM they could obtain it quickly, but nope. You need to cross the whole ocean the slow way if you miss Strength.
Regardless, we spoke with Jasmine, triggered the lighthouse quest, and surfed over to Cianwood with a swiftness. I was quite desperate to lift the level cap since our entire party was pushing level 30. I didn’t expect that we’d need everyone for the fight against Chuck, but I didn’t want to take any chances. As such, I skipped most of the trainers on Routes 40, and 41 with the intention of grabbing them on the way back to Olivine.
Somewhat predictably, the team did not have any issues clearing the Cianwood gym’s trainer battles. A whopping 80% of our team resists Fighting type attacks, which is a huge leg-up in battle. Evidently, resistances are very powerful when the majority of Pokémon are stuck with limited, or no coverage options.
Either way, my plan for Chuck himself was rather simple: Mabel. She quad resists Fighting type attacks, and Thunder Punch is Super Effective against Poliwrath. In addition, she also picked up Safeguard, so I could use that to block Hypnosis since Chuck’s strategy is reliant on putting his opponents to sleep.
As such, I led Mabel into Chuck’s Primeape expecting an easy W. Unfortunately, I made a bit of a miscalculation, and quite the opposite happened.
You see, I didn’t realize that Primeape had a Normal type attack, and expected Mabel would be able to easily shrug off soft Karate Chops. So you can imagine my surprise when I got nailed by Fury Swipes. Doubly so because Primeape landed the full 5 consecutive attacks, which nearly cleaved through the entirety of Mabel’s health bar. As such, she wasn’t going to have the necessary gas to defeat Poliwrath, which meant that my original plan for this fight was forfeit.

Well…shit. Now what? Sure, I’m ostensibly ahead because this fight is a 2 versus 5, but Sleep has a way of leveling the playing field. I’ve demonstrated that quite candidly with Trevor and Winston multiple times across this playthrough. As such, I’m quite worried about Chuck’s Poliwrath.
In my infinite wisdom, I decided to take a gamble. I let Mabel go down, and followed with Trevor who swiftly dispatched Chuck’s Primeape. From here, I’m betting that Poliwrath will miss Hypnosis, much like Morty’s Gengar, and I’ll be able to land Sleep Powder in retaliation. From there, I should be able to chip Poliwrath down with Super Effective Vine Whips.
Though, I was, once again, reminded of the power of Badge Boost because Trevor attacked before Chuck’s Poliwrath.

Huh? How?
How did a Pokémon with Base 55 Speed outrun a Pokémon with Base 70 Speed? Even accounting for Badge Boost, that interaction makes 0 sense.
Well, doing a bit of math after the fact, I figured out that Chuck’s Poliwrath has 51 Speed. That means we need a minimum of 47 Speed to clear 52 Speed with Badge Boost since Pokémon truncates decimal places instead of rounding.
So…how much Speed does Trevor have?

Well then. How fortuitous.
There’s a whole other discussion to be had about how Trevor even hit 47 Speed in the first place, but for now all you need to know is that Trevor is a very speedy plant. This allowed him to put Poliwrath to sleep before he could hit us with Hypnosis. Then it was just a matter of chipping the burly, blue toad down with Super Effective Vine Whips.
With that demonstration of Grass type superiority, we scored our 6th gym badge, and also relinquished our team from the suffocating level-cap of 30. With Jasmine on the horizon, we’re now free to go up to 35, though I severely doubt we’ll run into the level cap again throughout the remainder of this challenge.
Unfortunately, Chuck’s badge doesn’t unlock any other goodies for us since we don’t have a Pokémon that can learn Fly, but it does put us 1 step closer to closing out this challenge. Though, you’ll have to tune in next time to figure out how we do against Jasmine, and who our mysterious 6th team member is.
Full disclosure, I actually caught them already, but the story flowed better if we cut straight to Chuck. You’ll…see why in Part 7 when I talk about the Whirl Island detour.
Either way, thank you, as always, for reading. I hope you’ve had as much run reading about this ridiculous journey as I’ve had playing and writing about it, and I’ll see you in the next one.
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