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| CK 14 Draft Pick Trades - Aug. 13 | (newest trades on the bottom) |
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| Date | Players/Draft Picks | From | To |
| May 6, 10:08 p.m. | Jimmy Rollins (PHI - SS) | Michael Swithers | G.C. Rice |
| | Chris Davis (TEX - 1B, 3B) | | |
A | Plus Swids' 6th Round pick in 2010 | | |
| | Kevin Youkilis (BOS - 1B, 3B) | G.C. Rice | Michael Swithers |
| | Plus Sly's 9th Round pick in 2010 | | |
| May 14, 7:42 p.m. | Mark Buehrle (CWS - P) | Jess Kryscio | Brad Miller |
B | Plus Jess' 11th Round pick in 2010 | | |
| | Brad Lidge (PHI - P) | Brad Miller | Jess Kryscio |
| | Plus Brad's 13th Round pick in 2010 | | |
| May 21, 6:10 p.m. | Ryan Dempster (CHC - P) | Mike Fagan | Brad Miller |
C | Plus Fagan's 13th Round pick in 2010 | | |
| | Kerry Wood (CLE - P) | Brad Miller | Mike Fagan |
| | Plus Brad's 16th Round pick in 2010 | | |
| June 13, 10:42 p.m. | Jason Varitek (BOS - C) | Michael Bier | Jess Kryscio |
| | Mark DeRosa (CLE - 2B, 3B, OF) | | |
| | Adam Dunn (WAS - 1B, OF) | | |
D | Plus Bier's 5th, 9th & 13th Round picks in 2010 | | |
| | Vic Martinez (CLE - C, 1B) | Jess Kryscio | Michael Bier |
| | Chone Figgins (LAA - 2B, 3B) | | |
| | David Aardsma (SEA - P) | | |
| | Plus Jess' 10th, 14th & 17th Round picks in 2010 | | |
| June 15, 5:59 a.m. | Felipe Lopez (ARZ - 2B, 3B, SS, OF) | Brad Miller | Jess Kryscio |
| | Jason Kubel (MIN - OF) | | |
| | Mike Cameron (MIL - OF) | | |
E | Plus Brad's 4th & 7th Round picks in 2010 | | |
| | Michael Young (TEX - 3B, SS) | Jess Kryscio | Brad Miller |
| | Curtis Granderson (DET - OF) | | |
| | Plus Jess' 6th & 9th (from Bier 6/13) Round picks in 2010 | |
| June 16, 8:37 p.m. | Adam Dunn (WAS - 1B, OF) | Jess Kryscio | Michael Swithers |
| | Torii Hunter (LAA - OF) | | |
| | Mariano Rivera (NYY - P) | | |
F | Plus Jess' 4th, 8th & 13th Round picks in 2010 | | |
| | Brad Hawpe (COL - OF) | Michael Swithers | Jess Kryscio |
| | Aaron Rowand (SF - OF) | | |
| | Derek Lowe (ATL - P) | | |
| | Plus Swids' 2nd, 5th & 11th Round picks in 2010 | | |
| June 18, 6:10 a.m. | Mark DeRosa (CLE - 2B, 3B, OF) | Jess Kryscio | Brad Miller |
| | Casey Blake (LAD - 1B, 3B) | | |
G | Plus Jess' 11th Round pick (from Swids 6/16) | | |
| | Adrian Beltre (SEA - 3B) | Brad Miller | Jess Kryscio |
| | Nyjer Morgan (PIT - OF) | | |
| | Plus Brad's 6th Round pick in 2010 | | |
| June 20, 8:05 a.m. | Alexei Ramirez (CWS - 2B, SS, OF) | Jess Kryscio | Mike Trainor |
H | Plus Jess' 13th Round pick (from Brad 5/14) | | |
| | Yunel Escobar (ATL - SS) | Mike Trainor | Jess Kryscio |
| | Plus Trainor's 10th Round pick in 2010 | | |
| June 21, 12:38 a.m. | Brad Hawpe (COL - OF) | Jess Kryscio | G.C. Rice |
| | John Lackey (LAA - P) | | |
I | Plus Jess' 7th Round pick (from Brad 6/15) & 15th Round pick in 2010 | |
| | Hank Blalock (TEX - 1B, 3B) | G.C. Rice | Jess Kryscio |
| | Ryan Madsen (PHI - P) | | |
| | Plus Sly's 4th and 11th Round picks in 2010 | | |
| June 24, 6:29 p.m. | Adam Lind (TOR - OF) | Michael Bier | Matt Langan |
J | Plus Bier's 4th Round pick in 2010 | | |
| | Francisco Rodriguez (NYM - P) | Matt Langan | Michael Bier |
| | Plus Matt's 7th Round pick in 2010 | | |
| June 24, 6:29 p.m. | Paul Konerko (CWS - 1B) | Michael Swithers | Matt Langan |
K | Plus Swids' 7th Round pick in 2010 | | |
| | Huston Street (COL - P) | Matt Langan | Michael Swithers |
| | Plus Matt's 9th Round pick in 2010 | | |
| July 3, 11:17 p.m. | Stephen Drew (ARZ - SS) | Michael Bier | Mike Trainor |
| | Aaron Harang (CIN - P) | | |
L | Plus Bier's 6th & 10th Round picks in 2010 | | |
| | Jon Lester (BOS - P) | Mike Trainor | Michael Bier |
| | Rich Harden (CHC - P) | | |
| | Plus Trainor's 11th & 14th Round picks in 2010 | | |
| July 6, 7:10 p.m. | Adrian Gonzalez (SD - 1B) | Michael Swithers | Brad Miller |
| | Ricky Romero (TOR - P) | | |
M | Plus Swids' 4th Round pick in 2010 | | |
| | Todd Helton (COL - 1B) | Brad Miller | Michael Swithers |
| | Felix Hernandez (SEA - P) | | |
| | Plus Brad's 6th Round pick (from Jess 6/15) | | |
| July 19, 1:42 a.m. | Nyjer Morgan (PIT - OF) | Jess Kryscio | Michael Swithers |
| | Jose Valverde (HOU - P) | | |
N | Plus Jess' 11th Round pick (from Sly 6/21) | | |
| | Franklin Gutierrez (SEA - OF) | Michael Swithers | Jess Kryscio |
| | Andrew Bailey (OAK - P) | | |
| | Plus Swids' 8th Round pick (from Jess on 6/16) | | |
| July 27, 9:48 p.m. | Scott Podsednik (CWS - OF) | Jess Kryscio | Michael Bier |
O | Plus Bier's 8th Round pick in 2010 | | |
| | Yunel Escobar (ATL - SS) | Michael Bier | Jess Kryscio |
| | Plus Jess' 13th Round pick (Bier's original 6/13) | | |
| July 30, 9:28 p.m. | Clint Barmes (COL - 2B, 3B, SS) | Michael Swithers | Mike Trainor |
P | Plus Swids' 13th Round pick in 2010 | | |
| | Rafeal Furcal (LAD - SS) | Mike Trainor | Michael Swithers |
| | Plus Trainor's 15th Round pick in 2010 | | |
| Aug. 4, 6:20 p.m. | Todd Helton (COL - 1B) | Michael Swithers | Matt Langan |
| | Randy Wolf (LAD - P) | | |
Q | Plus Swids' 9th Round pick (Matt's original 6/24) | | |
| | Paul Konerko (CWS - 1B) | Matt Langan | Michael Swithers |
| | Ricky Nolasco (FLA - P) | | |
| | Plus Matt's 11th Round pick in 2010 | | |
| Aug. 8, 5:22 p.m. | Maicer Izturis (LAA - 2B, 3B, SS) | Michael Swithers | Brad Miller |
R | Plus Swids' 11th Round pick (from Jess, Sly's original (6/21, 7/19) | |
| | Asdrubal Cabrera (CLE - 2B, SS) | Brad Miller | Michael Swithers |
| | Plus Brad's 13th Round pick in 2010 | | |
Aug. 13, 8:44 p.m.
| Ryan Ludwick (STL - OF) | Michael Bier | Jess Kryscio |
| | Jose Reyes (NYM - SS) | | |
S | Plus Bier's 19th Round pick in 2010 | | |
| | Jason Kubel (MIN - OF) | Jess Kryscio | Michael Bier |
| | Plus Jess' 10th Round pick (from Trainor on 6/20) | | |
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