The key to repeat success is progression and evolution, or more simply KEEP MOVING. Milan was on the right track, solid buys, new Coach, and a brand new Scudetto, the first in seven years. The problem though was lack of movement and progress and it put us exactly where we are today. Winning the title was fantastic, Milan were playing hard-nosed efficient football with great balance and growing to be a great team. Sure they were lacking depth and the occasional injury or suspension made things difficult but the team persisted and ultimately survived. So much so they were in pole position for a repeat against a Juve team who were not resting on their laurels.
The problems really started that summer, purchases were not made and positions were not reinforced. A real LB was needed, a CB to replace the aging sun-setting Nesta, and a injection of youth in a few areas to compliment the players coming through the Youth system. All was not lost and by Christmas Milan remained at the top of the table, but it was that transfer window where Milan had their monumental moment of failure.
PSG offered 35M for Pato, a chance to play for Carletto and a chance for Milan to reinforce the attack that was at time comprised of Zlatan, a mis-firing Robinho, aging Pippo, and Cassano with a bad heart. On the roster was also a Pato who at the time had less goals that Muntari, which didn't stop PSG from offering a ton of money. It would have been the cash Milan needed and would have opened the door for Milan to seal the deal with Tevez. The rest well is history...
Milan don't sell Pato, lose 35M,
When you lose 35M Tevez does not arrive (ultimately ends up at Juve),
When Tevez doesn't arrive you are stuck with Pato who is dubbed a savior. Upon return from injury, he plays, Milan drop points in all three matches (Barca, Juve, Inter),
When you drop points it makes the Roma match a must win, Silva starts at less 100 fitness and gets injured, lost for season,
When you lose Silva for the season Milan don't win the title,
When you don't win the title you need money, Milan have none so cash is needed Zlatan and Silva are sold,
When Zlatan is sold Cassano opts-out, sold to Inter for Pazzo,
When you have Pazzo and Robinho on your roster and the Owner's daughter dates a player named Pato you dub him as the savior again, he fails,
When he fails you sell him to Brazil, the only place that will take him, for FAR FAR LESS than 35M,
When you don't have 35M you can't spend money so Milan struggle but ultimately punch above their weight finish in third,
When you finish third it still doesn't make you piles of money and you are 35M short so your management doesn't buy, no reinforcements no longer capable of punching above their weight
When you can't punch above your weight you get internal squabbles...Barbara, owner's daughter who dated Pato and kept him in town, decides she wants to run this sinking ship, Fester quits,
When Fester quits the Owner gets really freaking mad so Fester doesn't quit, now Milan has two CEOs to spend $0,
When you have two CEOs things don't go well and Allegri is fired,
When Allegri is fired you hire Seedorf,
When Seedorf arrives he is dubbed a savior honeymoon period lasts one match, a match they won on a dubious PK, Milan lose to Udinese in Coppa Italia
When you lose to Udine in the Coppa Italia you lose other matches as well, 7 total
When you lose matches you concede goals, 8 in two matches
The moral of this story, if you sell Pato you don't lose three straight and concede 8 goals in two matches! Hopefully you got a laugh out of this, or you find it entirely true.