Transactions 2009 Through Monday, June 15th
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Trades: Winged Buffalo traded Manny Ramirez to I Like Big Bunts for Javier Vazquez and Bobby Jenks.
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| Team Name | Replaced | Picked Up |
| Priory of Yawkey Way | Released - J.A. Happ | Ryan Madson |
| Winged Buffalo | DL - Coco Crisp | David Ortiz |
| BALCO Bombers | DL - Jake Peavy | C.J.Wilson |
| Reversal of Fortune | Released - Carl Pavano | J.P. Howell |
| WWEDD? | Released - David DeJesus | Gabe Gross |
| Priory of Yawkey Way | Released - Rich Hill | Activated - Dave Bush |
| BALCO Bombers | Released - Brandon Morrow | Activated - Tim Wakefield |
| BALCO Bombers | Released - Jerry Hairston Jr. | Activated - Jason Bartlett |
| A.C.L. | Released - Antonio Bastardo | Activated - Jonathan Sanchez |
| I Like Big Bunts | Released - Daniel Murphy | No Open Spot |
| I Like Big Bunts | Open Spot | Activated - Rich Harden |
| I Like Big Bunts | Open Spot | Brian Tallet |
| I Like Big Bunts | DL - Frank Francisco | Kiko Calero |
| The Bigg Doggs | Released - Mike Jacobs | Kevin Kouzmanoff |
| Reversal of Fortune | Released - Aaron Rowand | Activated - Jeremy Hermida |
| Reversal of Fortune | Released - Melky Cabrera | No Open Spot |
| Iron Men | Released - Hiroki Kuroda | No Open Spot |
| Iron Men | Released - Juan Rivera | Activated - Torii Hunter |
| Winged Buffalo | Released - Jarrod Washburn | No Open Spot |
| Winged Buffalo | Released - Carlos Marmol | No Open Spot |
| Non - Smokers | DL - Brad Lidge | Jason Marquis |
| Non - Smokers | DL - Jeremy Bonderman | Brian Bannister |
| Non - Smokers | DL - John Maine | Andrew Miller |
| Non - Smokers | Released - Fred Lewis | Marlon Byrd |
| Camel Jockeys | Released - Chien-Ming Wang | Ricky Romero |
| Camel Jockeys | Minors - Howie Kendrick | Emilio Bonifacio |
| Camel Jockeys | Released - Travis Hafner | No Open Spot |
| Reserve Moves | ||
| Priory of Yawkey Way | Reserved - Michael Cuddyer | Gary Sheffield |
| Reversal of Fortune | Reserved - Yadier Molina | Miguel Olivo |
| A.C.L. | Reserved - Chris Young (SD) | Jorge De La Rosa |
| A.C.L. | Reserved - Rafael Soriano | Jose Conteras |
| BALCO Bombers | Reserved - Denard Span | Carlos Gomez |
| Iron Men | Reserved - Jermaine Dye | Dexter Fowler |
| Sultans of Swat | Reserved - Roy Halladay | Activated - Jose Valverde |