Ryan Dempster, Theo Epstein Discuss Trades

June 5, 2012; Milwaukee, WI, USA; Chicago Cubs pitcher Ryan Dempster (46) during the game against the Milwaukee Brewers at Miller Park. Mandatory Credit: Benny Sieu-US PRESSWIRE

Chicago Cubs starting pitcher Ryan Dempster has been the subject of much trade speculation since the beginning of the season. The rumors were fueled to an even larger extent when Dempster told reporters that he would waive his no trade rights if it was in the best interest of the organization. Though, Dempster did say that he was hoping to get the chance to speak with Cubs’ president Theo Epstein.

Dempster had that opportunity on Wednesday of this week.

In a discussion that was seen around the world, Dempster and Epstein were observed in their discussion along the third base side of Wrigley Field. According to Bruce Levine of ESPN Chicago, Dempster and Epstein were discussing potential trades.

The only change to come from that discussion is Dempster’s pitching schedule. Rather than pitching on Saturday, Dempster will get the start on Friday and Jeff Samardzija will get the start for the Cubs on Saturday. The change does not appear to be an attempt to get Dempster one last start at Wrigley Field. Considering that the Cubs hosting the Boston Red Sox at Wrigley Field this weekend meaning the Dempster was in line to get at least one more start at Wrigley Field regardless of the case.

Friday, however, could be Dempster’s last start at Wrigley Field. As after Sunday’s game against the Red Sox, the Cubs will begin a six game road stand that sees the team travel to the South Side of Chicago to face the Chicago White Sox, and then to Arizona to play the Diamondbacks.

The common suggestion around the baseball industry is that Dempster will be the first significant player to be traded this season prior to the July 31 trade deadline. Reports have suggested that the Cubs could trade Dempster before the All-Star Break. There is logic to that suggestion. Both Epstein and Hoyer have admitted that the team is sellers heading into the trading month that are June and July. Other then the Cubs, Padres and Astros, there are no clear cut sellers. The Cubs have been the first team to announce to the public that they are ready start making trades. Dempster is expected to be the best starting pitcher on the trade market this season. A team interested in Dempster may prefer to acquire Dempster now, as that would give the veteran starting pitcher at least three additional starts with his new as opposed to having Dempster as a two-month rental if he is traded near July 31.

The White Sox are believed to have an interest in Dempster, but the Cubs and White Sox do not appear to make good trading partners. A majority of the White Sox prospects would not entice Epstein and general manager Jed Hoyer to trade Dempster to the White Sox. And, the White Sox do not appear to be willing to move the prospects that it would cost in order to acquire Dempster from the Chicago Cubs.

The New York Yankees and Los Angeles Dodgers are believed to be the two most aggressive teams in their pursuit of Dempster. Both the Yankees and Dodgers have the pitching prospects that would entice Epstein and Hoyer to make a trade involving Dempster. In the Dodgers case, the team attempted to trade for Dempster during the 2010 season, however, Dempster rejected the idea. With new owners in place and first place in the National League West division, Dempster may be ready to transform his Harry Caray impression into a Vin Scully impression.

One team that I have heard that has legitimate interest in Dempster is the Baltimore Orioles. The Orioles and Cubs have already had discussions about a potential Dempster, but as of yet, the discussions have not reached a point where the Cubs front office has asked Dempster if he would be willing to go to Baltimore. The Orioles also have an interest in Alfonso Soriano as Levine writes that the Orioles had one of their top talent evaluators watching Soriano this past week. It is possible that the Cubs and Orioles are discussing a package trade that would include Soriano and Dempster. Such a trade would be beneficial to the Cubs. For one they would get quality pitching prospects for Dempster, and they would have finally been able to rid themselves of the veteran slugger.

Dempster takes the mound for the Cubs today in what could be his last start at Wrigley Field.