1-Who is Milan's greatest goalkeepers ever? Milan have never had a World Class keeper, but who is Milan's best ever GK? Is it Dida despite making many mistakes?
For me it's Dida. Although Sebastiano Rossi on his prime (92-96) was also very good but as others and even Sacchi mentioned, this is because Rossi had the legendary back 4 (Tasotti, Baresi, Costacurta and Maldini) in front of him. Although Dida also played with good defenders in front of him (notably Nesta and Maldini), IMO Dida edged this one out. He (on his best days in 03-06) can really pull out some miracles.
2-This is for older fans, Who was better Cafu or Mauro Tassotti?
Tasotti. Cafu gave a lot to the offense with his speed but in terms of defending, Tasotti is better. Many have overlooked Tasotti's offensive contribution but as I mentioned in the Milan’s Greatest XI threat IMO this is because the midfield and attacking players are very good in doing their job and his contribution was mostly overlook. Tasotti was also adept in going forward and sending crosses. Tasotti also built very good partnership with the midfield (Donadoni, Rijkaard, Ancelotti, Colombo, Albertini, Boban) and created many one-twos moment that freed him. Abate for me is becoming a newer version of Tasotti, he just needed to improve his actual defending skill.
3-Who would you say is better Thiago Silva or Stam?
I'd say Stam although if T. Silva can really beef himself physically, he would win the contest. Stam was the real rock and simply annihilated the offense, period. T. Silva can still get the rattled by body check but never Stam. But in going forward and contributed to the offense flow, T. Silva (as we saw this season when he was deployed as DM) was better. Stam can also scored from dead ball situation (eg: CL 05 SF 1st leg vs Inter) but in terms of footballing skill T. Silva is better.
4-Desailly ior Gattuso who is better as a defensive midfielder
Desailly but mainly because he is taller and have more imposing physic. Gattuso rattled the ball-carrying player with his bull-dog passion and 'you-shall-not-pass' attitude but Desailly simply cut the opponent's offensive flow. In terms of ball distribution, Desailly is also better.
5-What was Frank Rijkard's MAIN position?
Holding midfielder. This can be an ambiguity with the DM position since he had Ancelotti and Albertini in his Milan days as his partner. Rijkaard was a very versatile midfielder (not to mentioned that he sometimes play as CB in Dutch NT). He had it all: aerial threat, ball distribution, tackles, passing, scoring. You can put him anywhere. In 91/92 and 92/93 MvBasten asked Capello to allow Rijkaard to play more offensive role and he scored 5 goals in 91/92 (his best ever tally in Milan). If you want to see a player that I feel resembled Rijkaard the most, the answer is Michael Ballack.
6-What was Ruid Gullit apart from being a striker, I know he played as a midfielder sometimes but was he an attacking midfielder, a deep-lying playmaker like Pirlo, a defensive midfielder or what?
Gullit was all of the above. Another very versatile midfield player like Rijkaard (they're both of the same age, born only few days apart in the same month and year and debuted in Netherland NT in the same game) but if Rijkaard's versatility was based on the defensive platform, Gullit's was based on offensive platform. In Sacchi's team, he was the striker partnering MvBasten, Virdis, Massaro or Simone but he was mostly use behind the striker and had free license to roam. In 06/07 CL, Kaka was registered as a striker partnering Inzaghi but in reality he was more a midfielder. That was Gullit's role in Sacchi's Milan. When the team was in need of additional offensive threat, another striker will be brought in Gullit will drop to midfield.
7-Who would you consider to be Milan's greatest ever striker?
Marco van Basten, no doubt. Some might argue that Sheva is better but that's another topic
I will not go waaaay back and talk about Gunnar Nordahl because that's waaaay beyond my years of following Milan.
8-Who was better Seedorf or Rui Costa or Kaka? (All at their prime)
Let's talk about Rui Costa first. For me he never reached his true potential in Milan that he showed in Fiorentina/Portugal NT and that always baffled me. In terms of passing, IMO he is better than Seedorf or Kaka.
Seedorf's main contribution for me was his intelligence in moving the ball into the penalty. He linked the midfields area and both sides of the field (left and right). Many have complained that he sometimes slowed down the tempo and I second that many times but many times he will wait for the others to join the attack and look for better options.
Kaka nailed this because of his skill, speed and a lot more deadlier. No offense but without him, we won't win CL 06/07.
9-Who was better Nesta or Costacurta
Nesta. For me pound by pound, Nesta's skill was a lot better than Costacurta. Nesta was very intelligent and was very graceful. Both are very good in positioning but Nesta is better in reading the game. Costacurta stopped the offense by clamping on the the striker carrying the ball while Nesta didn't even allow the ball to reach the striker. That's a difference.
- mind, he's improving in that after coming to Serie A.
I did'nt have chance to watch Rui during his time at Fio. Serie A wasn't broadcasted in our country until 2000-01. In Milan, his finishes sucked, you can count number of goals he scored for us with your hands. Vision and creative wise, Kaka' was pretty much at the same level with him