Update: Dempster suspended 5 games...

The suspension makes certain he misses a start.

With Petitte announcing his 2nd retirement, the Yankees will lose one of their most consistent starters. As if this was not bad enough, Rivera will retire as the game's best closer. More than likely, Derek Jeter will not be able to recover from his ankle problems and have to hang up his cleats. While Rivera & Jeter are HOF locks, Petitte will also be a strong candidate.

So my question is has a team ever lost 3 future Hall of Famers at once like this?

I can't find a team where three future hall of famers retired from the same team after the same season. There have been lots of teams with three and more hallof famers on it from Tinkers/Evers/Chance of the 1900 Cubs through the present (By the way, Tinker and Evers absolutely hated each other).

But I don't think Andy Pettite is a Hall of Famer. His 255 wins are more than a stone's throw from the "automatic" win total for hall entry, so other factors are needed. The necessary inquiry is whether he was dominant during his career, and he never led the league in wins, Ks or ERA, and not only did he never win a Cy Young, he never came close in balloting, finishing in the top three only once. He also has only 4 career shutouts. Bartolo Colon has three just this season.

What Pettite has going for him is his winning percentage, but that says as much, if not more, about playing for the Yankees on teams that won a ton of games. He also has more postseason wins than anybody, but you can't compare that honestly with players, who played before 1995 because there is an extra round of playoffs. And players before 1969 never played in any playoffs.

Bert Blyleven was the only pitcher under 300 Ws to make the Hall in 20+ years, and he had 288 for many teams below .500. I think we'll see several other pitchers below 300 Ws make the Hall in the coming years (Pedro, Smoltz and Schilling), but these guys were more dominant pitchers who gave up fewer runs. No current HOF pitcher has a higher career ERA than Pettite's.

And, as mentioned, HGH will also keep him out.

Pettite was a very good pitcher for a lot of years, but not a HOFer.

I agree with your assessment.

Rather than entering a dark period, the Yanks will have a single dark year. 2014 is when they will be under $189 million and save a lot of money moving ahead with the luxury tax.

After the dark year of 2014, the Yanks will be spending money to improve. With the surgeries to Banuelos and Pineda, there's no guarantee either will have a rotation spot. The youngster to keep an eye on is Jose Campos. He was a toss in for the Montero/Pineda trade, but might be the best player in the deal.

Despite dumping Scott Boras, Cano might still end up signing elsewhere. Someone will give the 30 year old, who won't run out ground balls, a 10 year contract. Remember when the experts said the Yanks had to sign ARod at all costs because they were moving into the new stadium? In hindsight, the Yanks should have let him walk.