Next few weeks the biggest of Pirates GM Huntington’s career

Acquiring Ryan Dempster could fortify Pittsburgh's starting rotation.

When Neal Huntington arrived in Pittsburgh in 2007, he had the assignment of rebuilding the Pirates to be a contender on a consistent basis. Huntington traded many popular players, such as Jason Bay, Jack Wilson, Xavier Nady and Nyyer Morgan. He brought back some good players in those deals, with the likes of Jeff Karstens and Joel Hanrahan. He even essentially stole James McDonald from the Dodgers in an exchange for Octavio Dotel.

The Pirates sit at 49-39 in leading the wild card race and trail Cincinnati in the NL Central by just one game. Huntington will ultimately be judged by what he does or does not do at the July 31 deadline.

The Pirates have some glaring needs as the deadline approaches. The first need could be a starting pitcher. Erik Bedard struggled in the first half of the season going 4-10 with a 4.80 ERA. Bedard has not been efficient in recent games, being only good for four or five innings. Kevin Correia did pick up his sixth win of the season in Milwaukee, but Correia will be a risk factor heading down the stretch.

So who should be on the Pirates radar to upgrade the starting rotation? First, let’s look at the best-case scenario. The two main targets (if available) at the deadline will be Cole Hamels and Zack Greinke. The Phillies have already gone on record saying they are going to offer an extension to Hamels in the immediate future. If Hamels declines the offer from the Phillies, then look for them to try to move him. The Phillies would most likely ask for a king’s ransom for Hamels. A king’s ransom could include some of the Pirates’ top pitching prospects Jameson Taillon and Gerrit Cole. According to sources from around the league, the Pirates do not want to part ways with these two.

The more affordable options could be a pitcher like Ryan Dempster. Dempster has been excellent this season for the Chicago Cubs and currently leads the major leagues with a 1.86 ERA. He also has a 33-inning scoreless streak going for him. The Cubs have made it obvious they would like to move Dempster soon so they can clear the way to move Matt Garza as well. Dempster would be a great fit in Pittsburgh already being familiar with the NL Central, and pitching in PNC Park never hurt anyone.

Other sources have the Pirates linked as a possible trade target for Boston Red Sox pitcher Jon Lester. However, once again the Red Sox would want a lot in return .

The realistic option for Huntington and the Pirates is to acquire a pitcher such as Dempster, Garza or Jason Vargas.

The Pirates are also aggressively searching for a outfield bat to help protect Andrew McCutchen in the middle of the order. The Pirates recently have been linked to a possible trade with the Arizona Diamondbacks for right-fielder Justin Upton. Upton makes perfect sense for the Pirates because they would control him for two years after this season. Upton is only 24 years old and would be a part of the future as well as the present in Pittsburgh. Arizona would be looking to acquire major league ready talent in a deal for Upton. The Pirates could part ways with top outfield prospect Starling Marte in order to make this deal happen. Arizona would likely ask for more than just Marte, so pitchers such as Brad Lincoln, Rudy Owens or Justin Wilson could be included in the deal. If the Pirates could land Upton without giving up Cole (yes, even dealing Taillon), it would be a very good move for this organization’s present and future.

The Pirates need to upgrade the corner outfield positions. Drew Sutton has had a nice season since joining the Pirates, but he has proved to be a liability in the outfield defensively. Perhaps, the Pirates simply call up Marte and upgrade the outfield in that way.

Regardless, these next two weeks will be a defining moment in Huntington’s career. The Pirates have made themselves into a contender, and Huntington needs to make the right moves to improve the Pirates roster. Huntington should have an all-in approach because this team and city are starving for October baseball.

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