I think the players you draft, sign, and trade for ought to match your philosophy of team payroll. Here is my Top 10 List for engineering a winning ballclub (sorry it's long): (1) Since the Cubs are a large market team with a large payroll, we can afford to sign other team's free agents to somewhat large contracts. We can also make trades for players in their arbitration years whose teams' can't afford them. (2) The Cubs brass need to take personal feelings out of contract negotiations and try their best to sign players who are in the primes of their careers or younger. We "reward" too many fan favorites with bad contracts past their prime years. (3) Contracts need to be slotted better. For example, It's OK for your cleanup hitter to make $10 million per year, but your long reliever can't be much over minimum. Making poor choices in free agency leads to salary slots not matching up, which leads to under-qualified players in important positions. (4) I believe that three starting pitchers should be "near-ace" quality, and the other two should be pre-arbitration pitchers with the possibility of becoming an ace. Those that don't meet expectations by their second arbitration year should be traded away to someone who sees their importance as a cheapish innings-eater. (5) I believe that the bullpen needs an ace closer (I know a lot of people disagree), as well as three reliable veterans (one of which can be the closer if needed) and 1-2 reliable youngsters. The closer's salary should not exceed the top five closer salaries in baseball. The veterans should not get longer than two-year contracts. (6) I believe that six hitters in the regular lineup should be paid well, but that every other position player needs to be traded away before their second arbitration year, or accept lower than market salary (like Koyie Hill). (7) Every position player should have a competent backup on the bench or at Iowa in case of injury. (8) Practice the "Rule of Two." A GM needs to pay a free agent based on their last TWO years of service, not just their most recent season. If a player has had one good year in the past two, their price should be cheaper than someone who has had two solid seasons in a row. (9) High-priced contracts need to end in a staggered way. Every year, a big contract or two should come off the books, allowing the team to invest in different areas of need. The Cubs have gone several years without many significant contracts coming off the books and that has handcuffed the team. (10) When trying to sign free agents, negotiate with several at once early in free agency. Let it be known publicly that you are negotiating with each free agent. Be completely willing to sign the first one who accepts your contract parameters. - Even with all that being said, plan for 10-20% "waste salary." This can include bad contracts, replacement players for long-term injured players, and players signed slightly over planned slotting. - To answer the question of this thread: (1) Draft and sign the best players available with an emphasis on pitching and power potential. (2) Trade minor leaguers away when their value is highest (Chris Archer, Robinson Chirinos, Brandon Guyer) and don't look back. Some will come back to bite you, but if the players you got back in return have value, then you've done a good job. Don't trade the players you believe in most, but have legitimate reasons for believing in them! (3) The AAA club should be filled with potential backups for the major league club. If the players you've developed are ready to perform, then they should play in Iowa, but if they still need more time, a former major leaguer should take their roster spot at Iowa and be ready in case of injury. (4) Collect major league-ready pitchers who can be shuttled between Iowa and Chicago and can be used in trades. When they are over-performing in AAA, trade them while they're hot, assuming that one pitcher is as good as another. The Cubs have been good at this in recent years!