@dccomicsrule2011: Thanks brah!
While I am a Boba Fett expert, I am by no means an expert on Master Chief. I've only Halo once in my entire life at a friend's house (it was Halo 1 and IV). So keep in mind that my assessment of this battle is based off a rough understanding of Master Chief.
That said, I do believe Boba has Master Chief grossly outmatched in terms of weaponry. Here's the difference between Boba and Chief: Both have some great durability. Master Chief has his energy shields, while Boba has his Mandalorian armor. But Boba has many means of getting through Chief's defenses, while Chief has few in comparison, especially in this scenario. Boba's Mandalorian armor is not to be underestimated. It has tanked blaster bolts effortlessly, practically tanked a direct impact from a small missile, has withstood his own flamethrower, and has gotten out of a speeder accident with minimal injuries. Meanwhile, based off my multiplayer experience, assault rifles (which doesn't seem to be that powerful) and SMGs (a tad better in terms of their power) seem to get through energy shields with relative ease. For the most part, I don't believe Jon's guns have a powerful enough effect to get through Boba's armor. Maybe after many magazines, he'll be able to. But he wouldn't be able to get through Boba's armor as easily as Boba could get through his. John's only prayer is his grenades. But with that armor and jetpack speed to boot, I don't think they'll be taking Boba down any time soon.
Boba has arguably one of the most lethal arsenals in the world of street-levelers. From mini-concussion missiles which can be powerful enough to obliterate a gigantic droid, to a sonic detonator, to that gnarly EE-3 Carbine Rifle which literally has a "disintegration" mode (hence that famous saying from Vader "No disintegrations"), Boba has lots of firepower and he knows how to use it.
Keep in mind that this is the most fearless bounty hunter in the galaxy. People think that he's a total n00b since he got his butt handed to him by a blind Han Solo. But this isn't Movie Boba Fett. This is EU Boba Fett. Boba Fett in the Expanded Universe has defeated Jedi like Rahm Kota, Jaina Solo, and even a deformed Starkiller clone which nearly speed blitzed him. In close combat. This is consistent with the fact that Boba was trained by his father Jango, the man who killed 20 Jedi with his bare hands! Powerful and influential people like Darth Vader and Jabba the Hutt have Boba on speed dial because they know he's the best.
So now that I've established that Boba isn't the amateur some people take him out to be, let me also reiterate on another advantage Boba has here: flight. Boba's got a jetpack. Whereas Master Chief can only jump higher than most people. That jetpack has the maneuverability to avoid a volley of X-Wing and Y-Wing blaster cannon fire. Boba has a huge speed and mobility advantage with that jetpack here. With it, he could fly circles around Master Chief and rain down hell on him.
Another thing I want to point out is that Boba is a bounty hunter. The guy has numerous ways of detecting Master Chief via infrared, audio filters, etc.
In conclusion, I think Boba pulls out a solid victory over Chief. John might have him bested in overall physique, but I don't think that'll be able to come to play here very much. Boba's an impressive gunslinger himself, and I see Boba's arsenal and speed/mobility advantages just being too much for Master Chief here.
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