@Region Philbis,
He was a multiple recipient of Roberto Clemente award. That award is granted to special type of ball player. It's dedicated to rewarding a player for contributions on and OFF the field. Bottom line is that he's a real mensche. To say the least, he has never caused a problem within any organization to which he's been associated.
I wonder if, once he hangs up his cleats, making him the pitching coach is enough. I'd love to see the organization within the minor leagues benefit from his talents, should he be willing to go that way.
From Wiki:
"Wakefield is well known throughout Major League Baseball as one of its most charitable players. He has been nominated eight times by the Red Sox for the Roberto Clemente Award, presented to the player who best reflects the spirit of giving back to the community, winning the award in 2010.
Since 1998, Wakefield has partnered with the Franciscan Hospital for Children in Boston to bring patients to Fenway Park to share time with him on and off the field. He has also hosted an annual celebrity golf tournament for 18 years. Wakefield has also been active with New England's Pitching in for Kids organization (a program dedicated to improving the lives of children across the New England region), the Space Coast Early Intervention Center in Melbourne, Florida, and the Touch 'Em All Foundation founded by Garth Brooks.
In 2007, Wakefield released a charity wine called CaberKnuckle in association with Longball Vineyards with 100% of the proceeds supporting Pitching In For Kids and raised more than $100,000."