This isn't second-guessing.  This is an illustration of how a GM who was not incompetent would have thought the '08-'09 offseason through.  Any one of us could have thought this through and not laid a turd in the '08-'09 offseason.

Oliver Perez?  His fastball has been losing velocity since 2004, and if it dips any more, his control problems will do him in and he could very easily fall short of replacement.  (Good thing I know what replacement is!)  Let someone else waste $4M on him.  We could use the picks to beef up the farm.

We need a relief ace pretty badly.  Our bullpen is a train-wreck.  Feliciano was more unlucky than bad and has a solid track record of being able to eat lefties and hold his own against righties.  So we will hold on to him (unless a no-brainer comes along).  What...somebody wants to give me a warm body for Schoenweiss??  I would have settled for a cold body that somebody needed to bury.  Done!  OK...back to business.  Frankie is an obvious choice, and we've got the cash for him, but he's coming off a career year in a meaningless category that might inflate his price tag disproportionately as compared to his real value.  We'll offer him what I think he's worth...$4M/year for three years.  If someone wants to give him more, let him risk it.  If it doesn't happen, we've got a solid guy in Fuentes and we can outbid the Braves (by just enough) for Rafael Soriano.  Trading Heilman would be selling real low...but his trends are not good, so we'll shop him.  One more year of sucking and we can simply trade him for a french fry; (he doesn't make much money).

Hmmm...the Mariners have something interesting on the table.  Putz for a boatload of average prospects.  Obviously this will require some negotiating.  Chavez for Reed isn't happening, but I can deal with Smith for Green.  And he is not getting Carp, Carrera, Vargas, and Cleto (maybe in 2007).  Considering the contract and the possibility of damaged goods, I'm keeping Carp..and he can take or leave the rest.  If Putz does well, I can get picks for him in 2010 when he leaves for free agency.  If he falls apart, such is life.

Hmmm...Lowe wants a fourth year, and at his age, that's probably going to bite us.  If we want to win in 2009, we'll need to pay that price (the Braves are looming).  If we play for 2010, we can pass on him and get some stopgaps.  Odalis Perez and Randy Wolf will be solid options for a year or two, and if Jon Niese dominates AAA, either one will be easy to trade (especially considering the bargains that these two underrated pitchers will get us in this market).  By 2010, F!Mart will be ready It depends on what we'll play for, but they're both good options.

Which do we take though?  2009 is risky.  The corners will be weak no matter what, Delgado is at a constant risk of tanking, and the Wilpons will not dump Castillo.  But it has good potential if things break right.  If F! and Niese don't work out, 2010 could quickly turn into 2011 or longer, and Lowe will be solid for at least 2 years, so I'm inclined to go for Lowe, and we'll still have Ollie's pick to compensate.  Santana, Lowe, Pelfrey, Maine, and Wolf will be formidable for a good chunk of time.  Santana, Mejia, Holt, Pelfrey, Maine, Gee and Niese, in the long run?  In addition to any surprises, drafts and minor-league trade acquisitions along the way?  I like it.

Corner outfield...it's weak and Danny Murphy is way too much of a regression risk.  Ibañez?  Type A?  With that kind of defensive liability for a very good (not great) hitter at corner outfield?  OK, he's in an extremer pitcher's park but the bad outweighs the upside here.  Do we want to take the kind of risk with Parker Bro...*ahem* Milton Bradley?  Delgado's a risk and he can fill in (poorly) at second if it comes to that.  Abreu, Burrell and Dunn are the best options, and Burrell is being lowballed by Tampa (and he was not offered arbitration!).  That clinches it.  Burrell it is.  Murphy will be a (potentially super) sub to spell Burell against tough righties and back up Castillo in case he tanks.  (We will let him sink or swim at second.)

If that's not enough we can shop Murph.  He's killing the winter league and someone might bite.  We could package him (with Carp, say) for a guy like (Lord willing) Adrian Beltre? 

So what am I doing for the short term and the long term?

Short Term:  Nice rotation.  3 of the best studs in baseball at premium positions.  Church has a mediocre bat for a corner outfielder, but his glove makes him an average player, and Burrel should be adequate.  Delgado with Evans to spell him against some lefties?  Let's cross our fingers.  Castillo?  If he tanks, we might have to put Murph in that position and again cross our fingers.  With Fuentes, Soriano, (perhaps K-rod) and Feliciano back in form (and without Schoenweiss) our bullpen should rebound (statistically, it's a certainty).  And Parnell and Kunz could mature.  Bench: Endy Chavez and some easily acquired strong backups.  With our 4 superstars, we always have a chance.  Estimated Cost: about $100M, but well-spent.

Long term: Schneider, Wagner, Delgado, and their contracts are gone in 2010, leaving us with only Castillo as a real albatross.  Wright and Reyes get raises, but are still well under market value.  We still have a very strong rotation and a good and inexpensive bullpen.  Ike Davis and Nick Evans are a good bet for a cheap and effective first base platoon in Ike finds his power.  F! should be ready.  But he might not be, and we have no catcher (Thole is interesting, though) or right fielder unless we resign Church (and we really would like a better option).  We have holes, but we only have $70M or so in well-chosen commitments and we'll have some money to spend to fill those holes if our prospects don't pan out.  (Matt Holiday comes to mind.)  The plan: F! Beltran, and Holiday in the outfield.  Wright and Reyes on the left.  Evans, Murphy, Castillo, and eventually Ike on the left (with an eye for a mid level and highly tradeable upgrade--Nick Johnson, Adam Laroche, Marco Scutaro, Mark DeRosa, Iwamura, or Adam Everett--if it's necessary).  Johan, Lowe, Pelf, Maine, Niese, possibly Holt and Mejia on the mound.  Soriano, K-Rod (or Fuentes) Feliciano, Parnell (perhaps) on the left.  Cost: if prospects pan out (and we can trade Lowe) about $115M (we add Holiday).  If not, about $135.  We'll have to acquire some mid-level talent like Laroche and Scutaro.

If injuries or power outages to key players kill us, those are the breaks, but it's a solid plan.