There is no instance in which Itachi is stomping Jiraiya, not the sick version the manga has presented us with.
Kakuzu gets stomped
Sasori gets stomped
Deidara loses
Kisame loses
Konan gets dragged in circles
50/50 w/ Itachi (highly circumstantial depending)
Obito stomps him
Nagato stomps him
Itachi beats Jiraiya with ease in every instance sick or healthy, and it's definitely nowhere close to being a 50/50. :lol
I'll just assume your definition of easy is MS.
Having to use MS doesn't mean that the actual amount of difficulty he'll have in the fight isn't anywhere close to being high enough to warrant this match being a 50/50.
50 meters apart in a forest is pretty favorable set up conditions for sound genjutsu. With the right tactics (and depending on knowledge) Jiraiya has odds.
Itachi has the overwhelming speed advantage, has the Sharingan, and Sound Genjutsu makes noise. There's no way Jiraiya is going to escape from his field of vision, hide so well that Itachi can't find him and prepare Sound Genjutsu, which will give up his location long before it's even prepared, and manage to cast it successfully.

*ease*
Yeah with ease clearly...stop fanboying him....*ease*
That's what the kid said:lol
Itachi has the overwhelming speed advantage, has the Sharingan, and Sound Genjutsu makes noise. There's no way Jiraiya is going to escape from his field of vision, hide so well that Itachi can't find him and prepare Sound Genjutsu, which will give up his location long before it's even prepared, and manage to cast it successfully.
When are you going to stop quoting me like your opinion is of any value?
Itachi is that many tiers above SM Jiraiya in speed to the point that it is overwhelming!?
Sound genjutsu will contentiously give up their location so the objective isn't so much to hide as it is to stall. Jiraiya and his summons can still act independently while the jutsu is being prepped, and stalling Itachi will be much much easier than fighting him.
Instant swamps with no warning covering large distances.
Trapping him inside a toad and forcing him to use MS to escape.
Gamabunta and his compares being a nuisance.
I personally think he can buy a good amount of time.
There are other arguments to be made in case he doesn't opt for Frog Call, but I just don't see this match-up being anywhere near easy for either contender.
The kid got triggered...I see...
Everyone's opinion has a value just like YOURS....you have a lot of things to learn and experience *son*
Jiraiya beats Sasori, Kakuzu, Hidan, Deidara, Konan and possibly Kisame. Obito, Itachi and Nagato stomp him.
How does Jiraiya counter C4? And Jiraiya beating Kisame doesn't even sound right tbh lol. I think Sasori might be capable of pulling off a W just based solely on poison tbh. Poison can take out anyone, summons included.
By evading it. C4 is a cloud of chakra released after a the giant bomb explodes. Jiraiya and/or the Toad Sages will sense the cloud.
Kisame would probably win unless he tries to drain Jiraiya's chakra directly from his body while he's in Sage Mode, because then he'd turn to stone and the match would be over. Otherwise all his chakra based techs are useless, his non chakra based techs are too weak to do lasting damage and his toad summons are easily defeated by his 10,000 (or whatever number it was) sharks or Daikodan. Kisame just needs to play it smart and not engage in close quarters due to Frog Call for paralysis + lethal attack
Sasori definitely loses. Iron Sand is easily evaded, Goemon handles swarms of puppets unrelated to the Kazekage and Jiraiya engages Sasori close up and obliterates him with Chou Oodama Rasengan.
I figured that was J-man's counter to C4.
Yup agreed.
J-man hasn't really been shown to be fast, correct me if I'm wrong? Iron Sand Drizzle was shown to break the sound barrier, and no other counter except for stationary defense was shown to be plausible. Of course the faster tier shinobi should be capable of dodging the technique, but is J-man actually fast enough to?
If he's unable to outright dodge the smaller variant of IS, having to constantly erect stationary defenses, I believe that puts him at disadvantage. Because one scratch, and its over seeing as the poison takes effect almost immediately, and paralyzes the body several seconds in.
Toads get taken out by ISD, especially the larger toads. If J-man isn't fast enough to evade ISD, or even gets a scratch its game over. I mean, and then you have the other shit Sasori has like poison gas, 100 puppets etc.
I just heavily believe J-man would be on the defensive here, and ultimately lose, because his toads are getting tagged by ISD, meaning they are done for at the get go, and without his toads J-man is kinda screwed I'd think.
Breaking the sound barrier is a feat that only requires a speed of around Mach 1 to 2. (It should be much faster than that though since Chiyo and Sakura couldn't dodge) FRS crossed a crater several miles in 1 second. That puts it far above Mach 1-2 in terms of speed. Pain was able to dodge Naruto's FRS. Jiraiya is faster than most of them, is in Sage Mode and has Sage Sensing unlike Chiyo and Sakura. Pretty sure he'll be able to dodge. Even if he couldn't, Giant Rasengan is strong enough to deflect the spikes.
Toads? Yeah, they get fodderized, but there's no reason to call them anyway. Sage Mode, Fukasaku and Shima are enough. One of the elder toads has Fuuton so that hard counters Poison Gas, 100 puppets are turned to ash by Goemon, and Sasori himself gets that same treatment. That or Rasengan.