1. Hire people who can evaluate players independently.
2. Hire people with the backbone to stand up for those opinions.
In many of the rumored iterations of the Johan Santana deal, Jon Lester was included. At this point in his career Lester was more promise than pitcher. Despite an 11-2 record over two seasons, Lester had a 4.68 ERA and was only striking out a few more batters than he walked. Despite the unimpressive numbers, Lester did have flashes of brilliance, including his start to finish a sweep of the World Series, less than a year after returning from non-Hodgkin Lymphoma.
From Buster Olney's Blog:
"In the midst of Boston's trade discussions about Santana, Red Sox pitching coach John Farrell all but threw his body in front of young left-hander Jon Lester, who had pitched a total of 144.1 innings in the big leagues at that point. Farrell argued that the Red Sox should keep Lester and not trade him for Santana, stating that the lefty could wind up winning more games than Santana over the course of Santana's contract. And Farrell has looked pretty smart so far: Lester has won 31 games over the past two seasons, Santana 29."
Without his time in the Cleveland Indians front office as the director of player development, Farrell might not have had the experience to identify the talent or the guts to strongly voice his opinion. Since not being included in the deal Lester has excelled, throwing 413.2 innings of 3.31 ERA baseball in the brutal AL East, including a spectacular year in 2009 where he struck out the second most batters per nine innings in the AL, only behind Justin Verlander. Lester also cost $38.5 million less than Santana. Also, it gives Sox fans one more reason to be happy that Farrell stayed with the Sox, instead of opting for the Cleveland manager's job in October.