It's no picnic building a team to compete in the American League East, and within this year's GM for a Day series, I've been tasked with doing so for both the Blue Jays and the Red Sox. Both of those jobs required a fair bit of background research to familiarize myself with the contract situations and the minor-league systems in order to craft rosters for 2011. Today, however, I take the helm of a team whose organization is far more familiar given my geography and extracurricular activites: the New York Yankees. Roll over, Brian Cashman, and tell Bob Watson the news.

The Yankees won 95 games in 2010, but by the high standards they set for themselves, the season was something of a failure. One year after winning their 27th World Series, the Yankees finished second in the AL East and had to settle for the wild card. Then after sweeping the Twins in the first round, they lost to the upstart Rangers in a six-game American League Championship Series. The pressure is on to return to the winner's circle, but then it's always on when you're wearing the pinstripes and answering to a man named Steinbrenner.

The Yankees failed to reach the World Series in large part because of the collapse of their rotation. In the second half of the season, their starters put up a 5.24 ERA, worse than every AL team except the Royals; excluding CC Sabathia, it was 5.91. A.J. Burnett and Javier Vazquez became two of the league's most disaster-prone starters, Phil Hughes put up a 5.07 ERA after June 19, and Andy Pettitte missed most of the second half due to a groin injury. In the postseason, the rotation was rocked for a 5.23 ERA with just four quality starts out of nine. In the ALCS, those starters were blitzed for a 7.10 ERA.

The obvious solution is to throw money at Cliff Lee, the top free-agent starter on the market, but he's hardly the only free agent priority. Pettitte, Mariano Rivera and Derek Jeter—three-quarters of the homegrown "Core Four" which has anchored the seven pennants and five World Series the Yankees have won from 1996 onward—are free agents as well, and it's a delicate act to figure out how to keep them in pinstripes. I've also got a big hole to fill in the bullpen with the departure of Kerry Wood, who became the team's top set-up man after being acquired at the trade deadline. The bench needs work as well.

The outside supposition is that the Yankees have an unlimited amount of cash to play with, but there's plenty of evidence to suggest that even they have an upper limit, starting with Hal Steinbrenner's stated desire to keep payroll "at the same level" as in recent years. Loosely translated, that means an Opening Day payroll somewhere just north of $200 million. The Yankees have been above that mark four times in the past six years. They've been above $205 million in three of those years, including 2010 ($206.3 million), but they've never been above $210 million, topping out at $209.1 million in 2008. Similarly, while they've shown a willingness to add payroll in-season via trades, their year-end payrolls —which tally the incentive bonuses, buy-outs and other benefits they actually paid over the course of the season, as well as the base salaries—have never topped $225 million. While we don’t have those figures for 2010 yet (the commissioner’s office generally releases them right around Christmas time), they ranged from $218-$222 million between 2007 and 2009, again a very narrow band. Adding a further drag on payroll, every dollar above $178 million is subject to a 40 percent luxury tax in 2011.

Having gone through the nuts and bolts of the payroll situation just after the end of the season, my best estimate using the figures from Cot's Baseball Contracts is that I've got about $146 million committed to 14 players who will count towards the opening-day payroll. Alex Rodriguez ($32 million), Sabathia ($24.3 million), Mark Teixeira ($23.1 million), Burnett ($16.5 million), Jorge Posada ($13.1 million), Robinson Cano ($10 million), Nick Swisher ($9.1 million), and Curtis Granderson ($8.25 million) are all locked into multi-year deals (I'm excluding Damaso Marte, who will earn $4 million, but start the year on the 60-day DL). Brett Gardner, Alfredo Aceves and David Robertson are all in their pre-arbitration years and will have salaries of less than $500,000. Hughes, Joba Chamberlain and Boone Logan are arbitration eligible; I've figured $4.5 million, $2.5 million and $1 million for that trio, respectively. That leaves me with two holes in the rotation, plus one at closer, one at shortstop, one at DH, and the rest of my bullpen and bench. Given that Jeter, Pettitte and Rivera made a combined $49.35 million last year, I've got very little room to sign all three plus Lee without blowing past the $210 million mark.

How badly do I need Lee? That's the real question in a rotation where even Pettitte's return isn't a given because he's said to be mulling retirement; yes, he's done that before and he's always come back, but he certainly sounds serious this time around. The free-agent market for starting pitching behind Lee is particularly slim. Ted Lilly and Hiroki Kuroda, the best available pitchers besides Lee, both re-signed with the Dodgers, and Jake Westbrook returned to the Cardinals. So many of the other available options tend towards damaged goods (Erik Bedard, Kris Benson, Jeremy Bonderman, Doug Davis, Justin Duchscherer, Jeff Francis, Aaron Harang, Vicente Padilla, Brad Penny, Ben Sheets, Brandon Webb and Chris Young), or palookas (Dave Bush, Freddy Garcia, Kevin Millwood, Jeff Suppan). Of the small handful remaining, I'm not about to make the same mistake as predecessor Cashman did when it came to Carl Pavano, lest I be tarred, feathered, and chased into the Harlem River. If I choose to test the market beyond Lee, that leaves me with a small handful of choices: Bruce Chen, who looks to have had a career year in Kansas City; Jon Garland, who's coming off a very strong year in San Diego aided by ballpark and unremarkable competition; and Jorge de la Rosa, who has upside and health going for him—but then so did Vazquez.

Leaving aside Lee for the moment, I'm going to assume Pettitte won't return. That leaves a sizable void to fill, but I'm not going to overreact. One major reason Larry Rothschild was hired as the pitching coach last week had to do with an extensive interview process which included in-depth use of video when it came to Burnett, Hughes and Sabathia, so I'm going to assume his answers gave both Cashman and manager Joe Girardi enough reason to believe he could shore up Burnett's woes, which resulted in a 5.26 ERA, 1.2 homers per nine and just 7.0 strikeouts per nine. Even with that line, his SIERA was still just 4.42, so it would appear some regression is in order and that he can be at least league-average. Likewise, Hughes will be coming back from his first full season in the rotation and won't have to worry about an innings cap; with Rothschild's input, I see no special reason to fret about him.

What I'm going to do to cover for the loss of Pettitte is to do something Cashman resisted: restore Chamberlain to the rotation. The Yankees took a pitcher who once ranked among the game's top 10 prospects, a pitcher with three above-average pitches—certainly enough to succeed in a rotation—and jerked him around between starting and relief roles in the name of protecting his arm. They received diminishing returns for their self-imposed troubles, and clearly did no favors for his head, even if Joba wasn't the brightest guy in the world when it came to understanding the reasons behind the shuffling. Chamberlain has a career 4.18 ERA and 8.4 K/9 as a starter, and I have to believe Rothschild can help straighten out his mechanics while assisting with the mental side as well.

I do have other things I could try to do with Chamberlain: trade him as part of a package for Justin Upton. Figure him and one of the "three B's" (Dellin Betances, Andrew Brackman, Manny Banuelos) from a system which is brimming with pitching talent and unlikely to find room for all three in the coming years (consider how hard it's been just to get Hughes and Chamberlain into the same rotation); their stock might never be higher than it is right now.

It'll take more than that to get a deal done, of course. I'm unwilling to part with Jesus Montero (more on his spot momentarily) but could bear trading the more defensively sound Austin Romine, or even 17-year-old catcher Gary Sanchez, who tore up the Gulf Coast League this year; I call him Gary the Unicorn because he's so wonderfully magical that I don't actually believe he exists, nor that I'll ever set eyes upon him. I could add another lower-ranked prospect for ballast, but I'm not willing to go much further than that to land the 23-year-old Upton, about whom there are reasons to be wary, starting with his shoulder. Then again, the same can be said for Chamberlain; neither is coming off the best year of their young careers. If the deal doesn't get done, it doesn't get done, and I'm happy with the bang for my buck provided by my outfield of Gardner, Granderson and Swisher. If it does get done, I can shop one of those for a starter to replace Chamberlain and shed a bit of salary, or hope that Pettitte reconsiders.

The Jeter situation is one about which all too much ink has been spilled. He's a 36-year-old icon to whom the entire organization owes a debt of gratitude, and one who is in line to collect his 3,000th hit next summer, but he's coming off the worst season of his career with the bat (.270/.340/.370) and his defense is far below average as well. Luckily for the Captain, the free-agent market for shortstops is rather grim, full of the similarly aged Orlando Cabrera, Edgar Renteria and Miguel Tejada, none coming off strong years or with anywhere near the value to the Yankee brand as Jeter. Negotiating this deal is a no-win situation, except for the fact that I'm about 110 percent sure that at the end of the day, the Yankees will have the highest bid out there. I'll play good cop by improving upon the Cashman regime's coolly received opening gambit of three years and $45 million, but not by much. I'll add a vesting option for a fourth year and go up to $17 million a year. I'll even offer to talk to the Steinbrenners about a stake in YES, but I'm not going four, five, or six years guaranteed. When Casey Close, Jeter's agent, again tells the press how baffled he is over these negotiations, I'll invite him to solicit bids from the other 29 teams and get back to me. It's a game of chicken I'm certain to win—and a winner's curse I'll be forced to bear.

Rivera, who's coming off a three-year deal worth $15 million a year, should be easier. I'll offer the same amount for one year, with an option for a second; if he wants two years guaranteed, I'm going to discount it because of his age (41 in a week), and shoot for $26 million, a per-year figure which still keeps him ahead of Brad Lidge and Francisco Rodriguez. Sure, he wants more than that, but again, I'm playing hardball and banking he won't go anywhere else.

As for the fourth member of the core, I'm onboard with the idea of Posada spending most of his 2011 as the primary designated hitter with occasional forays behind the plate so long as Montero, whose offensive upside has drawn comparisons to Miguel Cabrera and Frank Thomas, proves some level of adequacy while wearing the tools of ignorance. I'll still need some insurance if Montero's not ready, and I'm unwilling to put up with Francisco Cervelli for one more moment given his defensive lapses (14 percent caught stealing, 13 errors, tied with Jason Kendall for the league lead); I'm going to put Cervelli in a large wooden crate with sufficient airholes and see where it winds up when I stamp it for Anywhere Else, USA; I'm guessing it lands on Gordie Howe's front porch. Keeping in mind that Posada is a free agent after 2011, I'd like to try landing Miguel Olivo or Yorvit Torrealba for two years and $6 million, more money than either made last year; both are defensively sound if somewhat flawed at the plate, but I'm afraid that John Buck's three-year, $18 million deal with the Marlins has blown that market wide open. Until Romine is ready, a defensively capable member of the International Brotherhood of Backup Catchers will suffice. Chad Moeller knows the Yankees staff and the drill; I can see what shakes free come non-tender time, or look for a further upgrade in spring training.

Without Lee and Pettite, I'm at about $177 million now, and the hole in my bullpen is a bit bigger for having moved Chamberlain forward. Assuming that I'll have to top Sabathia's $23 million average annual value, I'll go $24 million per year for Lee—not an off-the-charts amount—but "only" for a maximum of five years because he's older than Sabathia was when he signed. Assuming I can land him, I'm going to backload the deal to leave a bit more breathing room for 2011; considering that Lee made $9 million last year, doubling his salary to $18 million in year one of the deal and climbing from there shouldn't be too tough a pill to swallow. If Texas hangs around the bidding too long, I'll consider a vesting option for a sixth year, though these long-term pitcher contracts give me the hives.

That leaves about $15 million to salt around the bullpen and bench without going over the $210 million mark. For the bullpen, I'll offer Wood two years and $10 million to return as my set-up man—I quite liked his work—and if that doesn't work, which I don't think it will, I'll shoot for Jesse Crain or Jon Rauch, both Type B free agents who made less than $2 million last year, and who should be available for about $5-$6 million over two years. One of those three will join Robertson and Logan as my top set-up men, with Aceves and Ivan Nova in middle relief roles. I'd like to add another situational lefty for cheap; Will Ohman or Randy Flores could do, and if I miss out on Wood I could even pair Pedro Feliciano, who'd probably cost something like $3 million a year, with my righty free agent. Either way, figure I'm spending about $6 million on those two spots.

For the bench, I have my eye on Bill Hall, who'd allow me to stick Ramiro Peña in the Cervelli crate (I'll throw in a bit more shredded lettuce; they'll have fun) and who can legitimately back up at second, short, third and all three outfield positions, just the kind of utilityman you need if you're going to carry three catchers, and the kind worth paying for even given his flaws. That would leave me with Eduardo Nuñez in Peña's role for the other infield bench spot and pinch-running purposes. I've got space for another backup outfielder; Laynce Nix has some pop and the ability to cover center, Jeremy Hermida might be worth another look, Melky Cabrera is homeless and shivering, and who knows what else might shake loose come non-tender time. Is Fred Lewis out of favor in Toronto now that Rajai Davis has arrived? It's worth a phone call. Figure one of those guys at a max of $2 million if I can't get Hall (who might cost more like $4 million); if I can get the latter, I'll settle for an outfielder from the Yankees' system—Greg Golson, Kevin Russo, Colin Curtis, the converted infielder Brandon Laird—making the minimum until the trade deadline hits.

I've built a lot of contingencies into this plan, so it may be hard to follow the accounting, but the non-Pettitte, non-Upton, non-Wood, non-name brand catcher payroll comes in at around $206 million for 25 players not including Marte, and $210 million with him. If Pettitte returns (for something around $10-12 million), I could work towards the aforementioned Chamberlain/Upton deal and if successful, move one of my two semi-expensive outfielders, perhaps filling in gaps along the bullpen/bench axis in order to cut down the number of other free agents I'm chasing. (See this Google spreadsheet for two payroll scenarios.)

So that's my plan. I've kept myself in the ballpark budget-wise while addressing the Yankees' biggest need (starting pitching), tried to play some hardball with the big names while still granting them top dollar salaries, put some faith in the personnel on hand who could reasonably be expected to improve on their 2010 showings, injected some youth into the lineup (Montero) and the rotation (Chamberlain) and worked to utilize what flexibility the roster affords given so many other long-term deals while assuming I won't get everything I want. It's an easier job than turning around the Pirates, the Royals or even the Blue Jays, but it's no picnic. Though in the worst case, I'm pretty sure I'll have a shot or two at rebuilding some other team somewhere come next winter.