Man, missing out on Michael Cooper is just going to drive me nuts. After going through Kobe's team I'm going to have to face Jordan's team? The team that stole Cooper away from me no less? Argh.
But I think I can make it, so this should be fun.
So on an individual to individual basis, I'm liking what I see so far. Outside of Kobe, I feel like I've got the better player at each starting position.
Mookie is a much better defender than Chauncey, who gets a bit of a reputation boost for being on the Pistons. Mookie was not as good of an offensive option, but he was still very efficient, with an A/TO ratio that topped out at 9.7 to 2.4. During the years I selected, he had many fewer assists, but this was because the Hawks no longer revolved around Dominique, and Mookie was asked to score by himself more. However, he's going to go back to more of his early role on the Hawks, bringing the ball up and letting the star players do the scoring. Chauncey will similarly have a small role in the offense, basically being a spot up shooter for Kobe, but Mookie is a significantly better defender. Given how they'll play, Mookie will be the better player in this series.
Hakeem clearly has the edge over Zo, there really isn't a question to it.
Buck is clearly a better rebounder than Bosh, but he'll clog up the paint since that's where he scored. He was a better defender than Bosh has been by a bit, but I don't think that Bosh has ever had fewer defensive responsibilities than he will have on my team. Plus, I'd like to point out that Buck only made the All-D teams many years later in his career than the years selected.
English could score a ton, but I don't think that he was overall a better player that Paul Pierce either. English's jumper was good, but did not stretch to the 3 point line. This is another guy who prefers to play close to the basket, although he doesn't live in the paint like Zo or Williams.
Of course, this isn't an individual vs. individual game. It's about matchups and game plans.
So to start, I'm happy to work primarily through two guys: Hakeem and Vince. Hakeem is a post up artist, who can embarrass any defender with his beautiful moves. Guys have to respect his pump-fakes from farther out too, since he could shot the J, and really do whatever he wanted. If he gets too much attention, he could and would kick the ball out. The reason I'm also going to lean on Vince is due to the matchup in particular. Kobe has gotten a lot of All-Defensive team nominations purely by reputation, and certainly wasn't playing defense as much with the Lakers in the years selected. He's sort of old at this point (not particularly, but you know, he's played a ton of minutes), and he likes to ball watch a bit and float around. He's not always engaged. Vince was an offensive force in his young days here, capable of not only knocking down threes easily, but driving and cutting up defenses, finishing with monster slams. I foresee a couple of occasions where Vince dashes behind an inattentive Kobe, gets a pass from Hakeem posting up, and finishes the play by ending the life of whatever poor sucker tries to rotate in front of him with an soul-shattering, Earth-shattering, rim-destroying, life-ending monster dunk. Poor dude might have to see a psychologist for PTSD after seeing Air Canada go nuclear on top of him.
Paul Pierce will serve as the clear 3rd option. He's also a great shooter, and very good at shaking defenders off the bounce and such. He's smart, and won't complain about not being the first option.
Bosh and Mookie will be the next two options. Both players have demonstrated that they can live practically getting frozen out on offense. Mookie spent a lot of time playing with 'Nique when it was the "slow the game down and get Nique the ball" show all game long, so he's perfectly content to be a bottom option on offense. Bosh too, he never really complained in Miami when he would get nearly no touches, so I don't have to worry about getting him the ball.
This offense works nicely in the modern age. Mookie, Vince and Pierce are all good 3 point shooters, and Bosh is a solid min-range shooter. They space the floor around Hakeem, allowing him to go to work one-on-one. Heck, even Hakeem can shoot. I can run a pretty straight forward inside-out game with this starting lineup.
On the defensive end, I feel pretty good too. Zo and Williams live in the paint, and English doesn't drag guys too far away from it either, so even if I didn't have solid defenders, I'd be able to slow guys down here. Hakeem can take on 'Zo one-on-one in the post and win, so I think that I can force TO's from this notoriously poor passer even without doubling him regularly, although since my SF and PF will be close the paint anyways, it won't be that hard to do. If Williams gets the ball, he'll have the same sort of problems. The paint will be clogged, and he's also a bad passer who is TO prone. Bosh may not be a stud defender, but he's got a size advantage on him and will be able to bother him straight up.
With the paint so clogged up, Kobe, English and Chauncey will have to essentially be jumpshooters all game. And even worse yet, among those guys only Chauncey is a real threat from 3 point range. I was a bit worried about who was guarding Kobe, but as Quotatious kindly pointed out:
Quotatious wrote:Both Vince and Paul have always done a very good job limiting Kobe's efficiency from the field
So I won't even have to worry about trying to hide the notorious Vince Carter on someone! He defended Kobe well!

On top of that, Mookie is an all-time great PG defender who can easily keep Chauncey uninvolved. Paul Pierce is no All-D team guy, but is a solid and heady player who can make English work. There will be no easy buckets for Quotatious' team.
You know what this does though? It encourages Kobe to shoot mid-range J's all day. He's good at that, but it's not the most efficient way to run an offense, especially when it means he's going to be freezing out a lot. I was really hoping to pull the old trick Russel would pull on Wilt in their playoff matchups. Russel would let Wilt score early on, and so the coach would have guys just feeding Wilt all game. However, his teammates would get sick of just standing around and watching Wilt do all the scoring. They wouldn't try as hard on defense because of it. Then in crunch time, Russel would turn up the defensive effort on Wilt, and if they even adjusted to Wilt not being able to score anymore, his teammates wouldn't be able to step up because they were all out of rhythm and dissatisfied anyways. This would be especially effective considering my team has an all-time great trash talker in Pierce, and two other psychos coming off the bench who would do anything to get in your head too.
Unfortunately, none of these guys really had ego issues at all.

Even English, who was a big-time volume scorer, I'm unhappy to read, was in fact a pretty relaxed teammate, who didn't demand touches or anything and would work off-ball. Zo is the only guy who might get a bit frustrated, but IIRC he wasn't some headcase, so I can't really rely on ego issues crippling the team.
That said, I'm happy enough as things are. His starters are going to be forced to shoot jumpers all day, with little 3 point shooting to up their efficiency.
Going to the bench, I've got a crack team of defenders everywhere but point guard. Rodman is a candidate for GOAT defender, slightly older Artest is still a force, Tree was a monster shot-blocker and Afflalo is a great hustle guy. I feel like he more deserves a D-team spot than Kobe over the last few years, but he never had the name to get on those teams, and he's not able to give as much effort on that side of the ball as a first option in Orlando. However, I'm slipping him back into his role-player days. He'll play good defense and shoot 3's all day.
JET will serve as the 6th man, like he did in real life. In the years I selected, he was knocking down 3's easily, shooting 42.3%. He'll be great at sparking the offense and spacing the floor like he does in real life. Afflalo's a good option too; he's capable of shooting from anywhere and has added a solid post game and passing to his arsenal. Artest was just above league average as a 3 point shooter in the years I selected, so you'll at least have to make like you respect his shooting. Rodman only provides boards and picks on offense, and Tree has no real scoring game either, but I don't plan on using Tree that often. I might role out some ultra-big lineup of Tree/Dream/Rodman/Pierce/Mookie just to play bully-ball for a little while. More often than that, I'll be running Bosh/Rodman/Artest/Afflalo/JET. With them, I can run a defense like Miami's, with Rodman and Artest being an upgraded version of LeBron/Battier. When Miami's healthy and playing hard, the defense is very effective and forces turnovers. Even if Quotatious tries to take advantage of Bosh guarding Zo, I can easily double him with my mobile forwards and force him to cough up the ball.
Obviously I've got to fill out my rotations and look at his bench some more, just some opening thoughts here.