Theo and Jed have a lot of buildin' to do. Although their first priority is almost certainly the acquisition of a manager/coaching staff, with the free agent season looming the Cubs new dynamic duo are going to have to do some hardcore assessment/evaluation, especially if they want to avoid a 100 loss season in their first year saving the Cubs.
That's right - I fully believe that 100 losses is a possibility in 2012. The Cubs are losing their two most potent hitters while several others are clinging on like so much deadweight. Hoyer's second priority (behind the pursuit and acquisition of Joe Maddon) should be to unload the cumbersome Alfonso Soriano, Carlos Zambrano, and other nutty contract/player still on the payroll for '12. Because realistically, folks, it's 2013 and beyond that the Cubs are building for. The Cubs aren't likely to get a lot for their pricey underperformers, but they are guaranteed to receive the freedom of not having to worry about them any longer. That's got to count for something.
In any case, I would characterize the following positions as top priorities to improve upon for '12 ('13) and beyond, via trade, free agency, or mind-blowingly good draft days.
1B, 2B, 3B, LF, CF, RF, SP x3, MR x2.
In other words, pretty much the entire team from the bottom up needs to be replaced. Considering the historic levels of toxicity that come with losing in Chicago over the span of several years, this makes sense.
On the Free Agent Market this year are a bunch of guys who can help, although it might be worth rolling the dice to see who's available next year. (Joey Votto for one.) Nonetheless, players who might lead the Cubs to their first World Championship since they invented the toaster include...
1B Albert Pujols
Why It Makes Sense: C'mon. The greatest player of his generation* is a free agent, departing the World Championship Cardinals - aka our most hated rivals. Pujols is on the wrong side of 30 but, unless St. Louis is willing to offer him a career contract - i.e., something that spans more than 6 seasons - the Cubs should consider doggedly pursuing him. Yes, I know, I was pissed when the Cubs blew a huge amount of money on Alfonso Soriano, but there's a few levels of excellence which separate Soriano at his best and Pujols even at his worst. Realistically Albert has perhaps 3, maybe 4 good years left in him, but they will almost certainly all be of diminishing returns. Still - if the Cubs can get him for no more than a 5 year deal, it's worth it.
Why It Makes No Sense: Albert will be "32" next year. Any contract he accepts will likely terminate no sooner than after his "36th" or "37th" year. He's deserving of perhaps 18+ million a year. If the Yankees were in play, he'd almost certainly find himself earning 25+ million. In any case, he's pricey.
(*although his actual generation may be up for debate)
Why It Makes Sense: Prince is under 30 and is playing a position that even a big man such as himself can have success at into his mid 30's. He's an incredible power hitter. He's batting .298 with 11 homeruns in 178 at bats at Wrigley Field. (Granted, this is against Cubs pitching...)
Why It Makes No Sense: I am 5'11. Prince is 5'11. Prince is listed as weighing 275 pounds. I once weighed 275+ pounds. I remember what I looked and felt like. Granted, Prince is an athlete and a lot of muscle beneath that fat. Regardless, I put absolutely zero trust in a 275+ pound player staying successful as he ages. Sooner or later, Fatty's gonna slow down. Not to mention Prince is probably going to command more years than Albert - 6+, maybe even as many as 8, and despite his youth I can't help but think that the second half of the contract is going to be a - no pun intended - deadweight.
Assuming that the Cubs aren't going to pursue Prince or Albert - hmm, Prince Albert? Is it a can filled with Poo-holes? - and, presuming that neither Theo nor Jed are dumb enough to attempt to fill the position internally, the Cubs are still going to have to either swing a trade or sign a free agent. I have no idea on what kind of trade options might be available, but on the market the choices are rather limited. Brad Hawpe is 3 years removed from his last good season, and is coming off a year in which his OPS in San Diego was .645. Casey Kotchman (whose name, for whatever reason, always sounds mildly vulgar to me) is coming off of a career year in which he posted an OPS of .800, batted .306 and slugged 10 homeruns in 500 at bats for the Rays. Derrek Lee is even older than he was when he first left Chicago (although he did kill it in Pittsburgh.) Lyle Overbay puts the "meh" in mediocre.
If the Cubs don't grab a top free agent, then my money's on a sweet trade of some kind. Alternative to that, I'd hope they look closest at Kotchman, who is under 30, hits just well enough to avoid my scorn, and would be a cheap choice allowing the Cubs to either build their war chest for when it matters or to pursue other necessary interests, like ... well, pretty much everything else.