I think Pierce is right. Or, at least, that was the plan. Danny gave KG a no-trade clause and signed Terry, Lee, Bass, etc. to long-term contracts. I imagine that he did that thinking that the team was going to try to win-now for the length of KG's contract.
Rondo's injury changed things, and was probably the event that changed ownership's thinking about the viability of winning now.
That's what I had offered in several forums going around at the time. Danny was locking this crew in for a few years and gambling on everyone's health for that timeframe. Rondo's injury crapped all over those plans.
For me, the biggest what-ifs are the ones that determine titles.
- KG's injury in 2009. that to me is the biggest because I truly believe it hindered his play the next season as well. I really think we could have 3-peated had he been continuously healthy.
- Powe's injury in 2009. With Powe, we would have had a competent 3rd big man to throw at Orlando to get to the finals. We needed another productive frontcourt player to go with Perk and Big Baby. We may not have beaten LA with just Powe and no KG but we'd have gotten to the finals.
- Perk's injury in 2010 finals. With Perk in game 7 there'd be many less offensive boards for LA and therefore less second-chance points keeping them in the game.
- Team laissez-faire attitude second half of 2010. Team played like crap (only the playoffs matter BS) after Christmas and it cost them homecourt advantage against LA. If game 7 is in Boston we win.
- Sheed's severe lack of conditioning in 2010. if he comes to camp in shape instead of playing into shape, maybe he has the stamina to produce more in game 7 as opposed to fading away.
- Shaq's health in 2011. If he's healthy enough to play the season and the playoffs, we have enough firepower to outplay the Heat who have no answer for him. Love Perk, hated the trade (at the time and the following year) and really appreciated the effort he made to come back early from his injury but he wouldn't have been a difference maker in that series. C's needed Shaq's offensive threat and defensive presense to win that series. I really think his presense would have made Green's absense and Rondo's injury moot.
Lots of good points, particularly the one about Powe—that doesn't seem to get brought up a lot around here. Of course, Powe's absence is probably moot if KG is there. My list of biggest what-ifs of the KG era:
1) KG's knee: I agree, we would've three-peated if it wasn't for this, no doubt about it.
2) Shaq's foot: Cs were steamrolling the league when Shaq was healthy; if he stays healthy, Boston wins the title.
3) Perk's knee: if he's healthy—which we especially needed with KG less than 100%—Boston wins in 2010.
These are my Big 3 (pardon the pun). In sum, if KG and Shaq don't miss significant time with major injuries, Boston wins 4 in a row—heck, maybe 5, since winning the previous 4 might've given them the momentum/health to beat Miami in the 2012 ECF—in which case the Cs have 20, maybe 21, titles, while the Lakers have only 14 (well, only 9 actually), and LeBron has no more than 1.
I know that the Cs had pretty much everything break their way during the Russell era—and I know I'm being greedy here—but why, oh why, can't the breaks once again really start going Boston's way? Len Bias, Reggie Lewis, McHale's foot, Bird's back, KG's knee, Shaq's foot, Green's heart, Wilcox's heart, Bradley's shoulders, Rondo's knee, Sully's back ...

Here's to hoping that Rondo, Sully, Bradley, Green, KO, and all other current and near-future Cs avoid severe injuries!
