Could Itachi have been part of Aka' before the Massacre.

I found this timeline on another forum to help me explain my point. It is apparently from the data books and I have taken only part.

56 BK
8 February - Sandaime Sarutobi is born.

48 BK
Shodaime and Nidaime found Konoha, the Village of the Hidden Leaf.

39 BK
Tsunade is born.
27 October - Orochimaru is born.
11 November - Jiraiya is born.

29 BK
8 January - Hyuuga Hiyashi and Hyuuga Hizashi are born.

17 BK
17 July - Shiranui Genma is born.

16 BK
8 March - Ebisu is born.
26 August - Momochi Zabuza is born.
18 October - Sarutobi Asuma is born.
21 October - Mizuki is born.

15 BK
20 March - Morino Ibiki is born.
11 June - Yuuhi Kurenai is born.

14 BK
1 January - Maito Gai is born.
15 September - Hatake Kakashi is born.

13 BK
26 May - Umino Iruka is born.
24 October - Mitarashi Anko is born.

12 BK
2 November - Gekkou Hayate is born.

7 BK
29 February - Yakushi Kabuto born.

5 BK
14 February - Ayame born.
9 June - Uchiha Itachi is born.

3 BK
9 January - Haku is born.
23 August - Temari is born.

2 BK
Mitarashi Anko becomes a Genin at age 10, begins receiving training from Orochimaru.
15 May - Kankuro is born.
12 June - Dosu Kinuta is born.
6 July - Kin Tsuchi is born.
14 September - Zaku Abumi is born.
27 November - Rock Lee is born.

1 BK
9 March - Tenten is born.
3 July - Hyuuga Neji is born.

2 BK ~ 0 AK
Orochimaru leaves Konoha village.
Uchiha Obito is killed. Hatake Kakashi acquires the Sharingan.
Yondaime is officially made the Fourth Hokage.

0 AK
19 January - Gaara is born.
23 January - Aburame Shino is born.
28 March - Haruno Sakura is born.
1 May - Akimichi Chouji is born.
7 July - Inuzuka Kiba is born.
23 July - Uchiha Sasuke is born.
22 September - Nara Shikamaru is born.
23 September - Yamanaka Ino is born.
10 October - Uzumaki Naruto is born. The Kyuubi is defeated. Yondaime is killed.
27 December - Hyuuga Hinata is born.

3 AK
27 December - Hyuuga Hinata turns 3. Hyuuga Neji, as a member of the Hyuuga Branch House, receives the Hyuuga Bunke Juinjutsu.
30 December - Konohamaru is born.
Sinobi Gashir of the Hidden Cloud attempts to abduct Hyuuga Hinata.
Hyuuga Hizashi is killed in place of Hyuuga Hiyashi.
The Cloud and the Leaf achieve peace.

5 AK
7 March - Hyuuga Hanabi is born.

8 AK
9 June - Uchiha Itachi turns 13.
June ~ July - The Uchiha clan is slaughtered by Uchiha Itachi.
23 July - Uchiha Sasuke turns 8.

9 AK
7 July - Akamaru is born.

11 AK
October - Rock Lee, Hyuuga Neji, and Tenten graduate from the academy.

12 AK
10 October - Uzumaki Naruto turns 12.
15 October - Series start. The Konoha Rookie Nine, including Uzumaki Naruto, officially graduate from the Academy.

13 AK
March~May: Team 7 is ordered to escort and assist Tazuna. Haku and Zabuza are fought and killed.
1 July - Chuunin Written Exam is held.
2 July - Chuunin Field Exam in the Forest of Death begins.
3 July - Orochimaru attacks Sasuke, and marks him with the Tenfuuin.
4 July - Fight with Dosu Kinuta and his team.
7 July - Chuunin Field Exam ends. Preliminary Chuunin Tournament is held. Zaku Abumi and Kin Tsuchi are killed.
July ~ August - Dosu Kinuta is killed. Gekkou Hayate is killed. Uzumaki Naruto learns to summon Gamabunta.
11 August - Chuunin tournament is held. Sandaime Sarutobi is killed.
13 August - Sandaime Sarutobi's funeral is held.
~27 August - Itachi and Kisame arrive in Konoha. Jiriaya and Naruto leave to find Tsunade. Kakashi and Sasuke put into comas from Itachi's Tsukiyomi.
28 August - Naruto begins training the Rasengan
29 August - Morning - Naruto completes part one of training; begins part two.
30 August - Naruto completes part two of training. Tanzaku Castle Destroyed by Orochimaru. Naruto begins part three of training. Naruto accepts Tsunade's challenge.
6 September - Sannin fight occurs. Naruto first uses the Rasengan.
7 September - Tsunade arrives in Konoha, officially becomes Godaime Hokage. Shikamaru promoted to Chuunin.
8 September - Naruto and Sasuke fight on the rooftop. Sasuke invited to join Sound. Sasuke leaves with the Sound Four.
9 September - Team Shikamaru forms, begins "rescue Sasuke" mission. Lee undergoes surgery. Chouji and Neji's battles occur.
10 September - Kimimaro appears and the remainder of fights occur. Sasuke and Naruto fight at the Valley of the End. Chouji and Neji undergo surgery. Sakura begins training under Tsunade.
December - Naruto leaves Konoha to train with Jiraya.

Now consider, Just before the time skip, Aka' have a meeting where they state that Oro' had left them 7 years earlier.

Oro' says himself that left because Itachi was too strong. In the flashback of the Itachi v Oro' battle Itachi is already in an Aka' robe.

This would mean that Itachi was an active member 7 years prior to the break.
If the break was at 13AK, 13-7=6AK. Before the Uchiha massacre at 8AK. Itachi would have been 11 when he joined Aka'. 2 years before the Uchiha Coup'. Could Madara have been Itachis teacher from 11 or earlier? Is this why Itachi was such a genius, and knew so many clan secrets? If Madara was hanging around for 2 years, Could Madara have planted the idea of the Coup'?

What do you think?

Some facts in the Timeline have been disputed but, not the ones I need here.

This is not my theory either, just putting it out there

alternative title:KISHI"S TIMELINE TROUBLE

How can the picture of Itachi v Oro' be of an 11 year old Itachi? He's meant to be younger than Naruto and the others at the beginning of part 1

Though, Itachi was always mature for his age.