In the United States, Major League Baseball's trading deadline passed today with some noteworthy moves by teams other than my Boston Red Sox.  Aside from my disappointment that the Red Sox failed to make an impact trade to help the team, I recognized something else...

First-year General Manager Ben Cherington has made some interesting trades this year, most where he seemed to give up more than he received in return.  (See Appendix A below for examples.)

In contrast (bad, free-agent signings aside), most of the trades orchestrated by former GM Theo Epstein seemed to yield more in return than whom he gave up.  (See Appendix B below for examples.)

Assuming that I'm right, what are the reasons for the differences?  

• Was Theo dealing from a position of strength while Ben dealt from a position of weakness?  
• Was Theo a better negotiator?  
• Was Ben more desperate?  
• Did Theo hold out for a better deal?  
• Did Ben concede too quickly?  
• Was Theo more willing to walk away?  
• Was Ben afraid of leaving the table with nothing to show for it?

Very often, the final stages of many sales cycles, especially those to large companies with procurement people, are negotiations.  Assuming that your salespeople have developed some compelling reasons to buy, and buy from you, then YOU have leverage.  They want what you have.  However, when your salespeople fail to uncover the compelling reasons to buy from you, then YOUR PROSPECTS have leverage.  You want their business.

Your outcome from a negotiation or competitive sales situation is in direct disproportion to how badly you want the business.

Appendix A - Examples of Cherington Trades

He gave up top Sox prospect, Josh Reddick, and in return received Andrew Bailey, who has been on the Disabled List (DL) all year, and Ryan Sweeney, who has been on the disabled list three times already this year.

He gave up 3-time All-Star Kevin Youkilis for a minor league pitcher and a utility player whom they have already traded away.

He gave up a good hitter, Jed Lowrie, for Mark Melancon, a relief pitcher who has just plain sucked for the Red Sox this year.

As compensation for letting Theo Epstein move to the Cubs, he received an injured minor league pitcher, Chris Carpenter, in return.

Appendix B - Examples of Epstein Trades

He gave up 3 talented minor leaguers and got All-Star first baseman Adrian Gonzales in return.

He gave up a talented minor leaguer and got All-Stars Josh Beckett and Mike Lowell in return.  Beckett and Lowell, along with Curt Schilling below, helped them win the 2007 World Series.

He gave up 4 young pitchers, none of whom panned out, for Curt Schilling.  Schilling helped them win the 2004 World Series.

He traded disgruntled All-Star Nomar Garciaparra for Orlando Cabrera and Doug Mientkiewicz, both who helped them win the 2004 World Series.

He traded clubhouse cancer and multiple performance-enhancing drug offender Manny Ramirez in a three team deal for Jason Bay.