Roster Doctor helps an expansion team

Hey Doc,
(the league is a 12 team, 6×6 mixed roto league (standard 5×5 + .OBP, and QS) where teams can keep up to 10 guys)

I need some serious help! I joined an established keeper league this year as one of two expansion teams. Somewhat regrettably, this year started off with a questionable move in early March; trading Adrian Gonzalez, Justin Verlander, and Justin Upton (3 ‘expansion draft’ players) for Jason Heyward, Brian Matusz, Drew Stubbs, Alex Rios and a 1st round pick (Shaun Marcum was drafted with that pick) … Can you say backfire? How busty are Alex Rios and Brian Matusz? Ouch, it would have been better off if no one was in those slots. Oh well.

Here is the current roster after some FA moves and trades:

C- Brian McCann
1B- Freddie Freeman
2B- Michael Cuddyer
3B- Chase Headley (waiting on Lawrie)
SS- Yunel Escobar
IF- Eric Hosmer
OF- Jason Heyward
OF- Brennan Boesch
OF- Eric Thames
OF- Cameron Maybin
Util- Jemile Weeks
B- Bobby Abreu
B- Bryce Harper (First spot given up for a high quality idle keeper)
B- Brett Lawrie (Hand injury killed 3rd base, was planning on replacing Chipper with this guy)
B- Desmond Jennings (Rays not calling him up is hurting)
DL- Chipper Jones

SP- Mat Latos
SP- Madison Bumgarner
SP- Anibal Sanchez
RP- Kevin Gregg
RP- Tyler Clippard
P- Ian Kennedy
P- Homer Bailey
B- Andrew Miller
B- Scott Baker
DL- Stephen Strasburg (Second spot on the roster given up for an idle keeper)

I was also “lucky” enough to have drafted Ryan Dempster, Travis Wood, Chone Figgins, Manny Ramirez, Maglio Ordonez, Derek Jeter, Brandon Lyon, and David Aardsma (to go with Brian Matusz, and Alex Rios)… Needless to say by the middle of May I was selling off pieces for prospects and draft picks. It went ok, as I flipped a lot of Free Agents and weak performers into a prospect hot-list and, collected six first round picks (that’s right six out of 12) for next years draft. (The #1 waiver priority also locks up Goldschmidt, or the-next-big-prospect when they break into the FA market).

I’ve been willing to give up winning this year to set up a dynasty, and I’ve been attempting to stack up young talent since May, but who else should I be targeting? More importantly, what do I have that has trade value for contenders? I’ve almost lost touch with this concept this season (example: Hosmer has more value to me than a Konerko, and I would even have a hard time selling him for Teixiera cause of the youth and upside). Most offers other managers send seem borderline disrespectful. For instance, I personally love this pitching staff. They’re all in their primes and doing very well this year, but they don’t seem to be bring back much of a return in trade talks. What’s going on?

Please Doc, help me out.

Robert –

Being an expansion team is always tough. If the older teams in your league get to protect their best players (and then keep them for as long as they wish), then it can take a while to build a competitive team. In your league’s case though, it looks like you were able to get your hands on some top tier talent in the expansion draft. Unfortunately, your March trade eviscerated your squad.

Let’s let bygones be bygones and work with what you’ve got now. Now you must be in rebuilding mode. Rebuilding is an art. The key is synchronizing your players. A rebuilding team looks to the future, obviously. But how far into the future should it look?

In part the answer depends on you, the owner: how many seasons of non-competition are you willing to endure (and pay for)? What is your tolerance for risk? Part of the answer depends on the league. In your league’s case, with some but not many keepers, there should be some good talent still available on draft day. But the top tiers will obviously be gone.

As it stands now, you’re not likely to have enough top talent to compete next season. McCann is probably your best keeper. Guys like Heyward, Hosmer, Freeman and Bumgarner might go in the fringe of the top 10 rounds in a redraft league and if they are ever top tier talent it probably won’t be next year.

So I would shoot for the following year. Keep Harper if you like, but I would generally try and focus on slightly more mature hitters like Heyward, Hosmer and Freeman. They are more likely near their primes by then.

Players like Matt Wieters, Cameron Maybin even Adam Jones aren’t likely to be kept and are all worth taking a risk on next year to see if they truly blossom into the top tier.

Teams probably keep three to four pitchers out of their 10 keepers. A player like Gio Gonzalez isn’t likely to be kept but may be keeper worthy the following year. As may be Jonathan Sanchez. It is ok to go a bit younger and rawer with pitchers too, so maybe you want to target a Matt Moore too.

So I’d use your keeper spots to target some of the more unproven guys with raw talent. Since these players aren’t likely to contribute much this season, you should have an easier time prying them away from your opponents.

I’d use your many draft spots to go for the fringe players that owners aren’t going to keep, like Wieters. And then I’d hope for some serious breakouts.