It is probable that the Red Sox will not play meaningful October baseball. They still have a puncher’s chance but it is unlikely.
We will have a much better notion if the Olde Towne Team can make a push for the postseason after the series with the Rays on August 29. It should give the front office just enough time to place the free agents to be on waivers, so they could be moved before September 1.
Free agent draft pick compensation is a valuable asset, but attaining prospects of the same talent level (i.e. a top fifty pick) is a better alternative for the following five reasons:
1) The team does not have to risk that the free agent will accept arbitration and potentially overpaying for the player the following year.
2) The acquiring team, in most cases, does not have to pay the prospect’s signing bonus.
3) The team does not have the risk of the draftee not signing and delaying compensation for another year.
4) The team has more and better information on prospects than draftees. In most cases, prospects have played more with wooden bats and against better competition. Hence, prospects are less risky assets.
5) The team does not have the risk of attaining a compensation pick outside of the first or second round. For example, Adrian Beltre signs with Baltimore this winter as does Derek Jeter. In this scenario, the Yankees would receive the O’s second-round pick and the Red Sox would get their third-rounder. Baltimore’s first-round pick would be protected as it will likely be a top fifth teen selection. Since Jeter is rated higher than Beltre, the Yankees get the O’s second-round pick and not the Sox.
If all reasonable hope is lost, then the Red Sox should place Victor Martinez, Beltre, etc. on waivers and try to move them. Prospects are better compensation than draft picks.