Shipman was selected in the Triple-A phase of the draft after being left off the Cubs' 40-man roster and Triple-A reserve list. He spent most of 2006 at Triple-A Iowa, where he appeared in 46 games and was 2-3 with a 3.81 ERA in the Pacific Coast League, striking out 43 and walking 27.
Shipman now joins his third organization after spending the past four years with the Cubs and Sox farm systems combined. He was traded to the Cubs in July, 2004, for veteran left-hander Jimmy Anderson.
"Shock," Shipman said Thursday when describing his initial thoughts of changing clubs for the second time in his career. "Shock was the first thing, then excitement. It's a chance with an organization that seems to like me and wants to give me a shot at pitching in the major leagues."
The A's paid $12,000 to acquire Shipman, who was previously classified to the Cubs' Double-A roster.
While he was disappointed not to make the team's Triple-A reserve list, Shipman refuses to cast any negative light on his former team and credits the Cubs for helping him mature as a pitcher the past three years.
"I thought I had a pretty decent year for my first year [at Triple-A]," Shipman said. "I can only credit the Cubs and their coaching staff for that and for helping me mature. I'm not going to lie. I was a little surprised that it happened the way it did. Obviously, that kind of hurts a little, but I'm just going to play baseball and not worry about the business side of it."
Shipman was signed by Boston as a non-drafted free agent in 2003. The University of Missouri alum had expected to be drafted after having spoken with several scouts from different organizations, but was mysteriously excluded from the draft due to concerns over his health.
When he was 18 months old, Shipman was toppled by a fish tank at his family's home and would lose all sight in his left eye. Since then, he's pitched with a glass eye that is practically unnoticeable to the casual observer.
As someone who pitches with sight in only one eye, Shipman is considered one of the more unique pitchers in baseball. Now he'll have a chance to pitch for a team that he considers one of the more unique franchises in the sport.
"I've heard a lot about their pitching philosophies," Shipman said when asked what he knew of the A's. "Throw a lot of strikes, get ahead of guys. Try to get through an inning as quickly as possible. That's the kind of guy I am, so hopefully it will be a good fit."
Of course, that was also the same philosophy held by Alan Dunn, Shipman's pitching coach and mentor the past two seasons. Dunn was recently named the Cubs' new Minor League Pitching Coordinator.
Shipman frequently credited Dunn as a key factor in his success the past two seasons, which culminated with an all-star appearance at Double-A in 2005.
When Shipman was sent back to Double-A for a brief 11-game stint following an inconsistent stretch with Iowa this past season, Dunn knew the instigating factor behind the demotion was simple: walks.
"I wasn't too concerned about his hits allowed," Dunn said at the time. "Obviously, you want to stay away from them, but I was more concerned with whether he was giving up a walk, and then giving up a hit. If you give up a hit but stay away from a walk, you still need to give up three more hits to score a run. But if you give up that hit, and then a walk, you're in trouble."
Before the demotion, Shipman had issued 19 walks and 45 hits in 37-plus innings. He closed with 56 strikeouts and 29 walks in 72 innings combined this season. Opponents batted .304 against him at Iowa.
"He showed himself to be pretty durable," Cubs Scouting Director Tim Wilken said of Shipman, who remained injury free in his tenure with the club. "I'm sure [the A's] acquired him to get some more depth in their system. By hook or crook, hopefully he'll find a way to get to the big leagues."
The first step toward achieving that goal will likely be another season at Triple-A and the Pacific Coast League. For Shipman, it's business as usual.
"I'm going to go to Spring Training with the A's, where I know a few guys that I played with in high school and college like Haas Pratt. I'm looking forward to it," Shipman said.
Shipman features a four- and two-seam fastball in his repertoire, which registers between 88-92 mph on most occasions. He also features a circle change, a slider and a curveball.
"I'm an aggressive guy," Shipman said when describing himself as a pitcher. "I want to get the job done as quickly and as painlessly as possible. I'm going to go out every day and give the same effort no matter if I'm pitching in a game where we're up two runs or 18 runs, or are down 18 runs.
"On and off the field, I'm the same guy. I don't go and do anything off the field that I wouldn't do on the field," he added.