This is GM Neal Huntington’s 10th trade deadline with the Pittsburgh Pirates. From the good, the bad and the ugly, we recap the previous nine as this year’s deadline looms closer.

Today, we’ll take a look at the deals made by Pittsburgh Pirates GM Neal Huntington in 2008. Having been hired late in the 2007 season, this year marked Huntington’s first deadline with the Pittsburgh Pirates.

Deadline Approach

The Pittsburgh Pirates were 50-58 at the deadline, so they were clearly sellers.

The farm system had a few promising players in the system, with Andrew McCutchen, Neil Walker and Steve Pearce cracking the Baseball America Top 100, but it was top heavy with no depth. Picking up a couple future pieces was the logical move.

July 26: Traded RP Damaso Marte and OF Xavier Nady to the New York Yankees; received RHP Jeff Karstens, RHP Daniel McCutchen, RHP Ross Ohlendorf and OF Jose Tabata.

Nady was in the middle of a career year, hitting .330 with 13 home runs at the time. Marte was averaging a strikeout per inning with an ERA in the mid-threes. Both had one more year of team control remaining, but the Pirates still got a good haul.

Tabata was viewed as the Yankees’ right fielder of the future, ranked as the 37th best prospect by Baseball America. He had his moments as a Pirate, but was eventually passed over for Starling Marte and Gregory Polanco. Speaking of having his moments, Karstens came four outs away from a perfect game in his second game. When healthy, he was a good backend starter. He was just rarely healthy. Ohlendorf was the Yankees’ ninth best prospect (according to BA) and had a solid 2009. He quickly teetered out, as did (Daniel) McCutchen.

The Yankees gave up a good chunk of their farm system to address two needs. The Pittsburgh Pirates seemed to be at the right place at the right time.

July 31: Traded OF Jason Bay to the Boston Red Sox; received 3B Andy LaRoche and RHP Bryan Morris from the Los Angeles Dodgers and OF Brandon Moss and RHP Craig Hansen from the Red Sox.

The build up for this trade is great. Manny Ramirez had completely worn out his welcome in Boston and needed to go. Los Angeles was desperate for offense, so they were a logical landing spot. The only problem is the Red Sox were still in the hunt and needed a quality left fielder. The Pirates provided the extra outfielder and grabbed some top prospects from both clubs.

LaRoche was ranked as the 31st best prospect by Baseball America, but like his brother Adam, he never panned out as a Pirate. Brandon Moss ended up living up to his “future slugger” billing, but not with the Bucs. Bryan Morris was a reliable part of the original Shark Tank and was flipped for a draft pick before he went haywire. Hansen was basically a throw in and fizzled out with the Pirates.

Bay fit in well with the Red Sox and the Dodgers won the division because of Manny-wood. The Pirates got the short end of the stick.

August 21: Traded 3B Jose Bautista to the Toronto Blue Jays; received C Robinson Diaz.

The Pittsburgh Pirates were convinced LaRoche was the third baseman of the future and gave him the job as soon as he joined the club. That meant the incumbent was free to a good home. Whoops.

Bautista went from a fringe-player to an All-Star and one of the best sluggers in the American League. Diaz got a cup of coffee with the Pirates in 2008 and part of a season as a backup the following year.

Hindsight

The Bautista trade may be one of the worst of Huntington’s career, but he only succeeded in Toronto by completely retooling his swing. He didn’t have a chance in Pittsburgh.

While none of the nine players acquired became main fixtures in the Pirates’ future, it’s easy to see why they made these moves. Picking up two top 40 prospects and a handful of highly rated pitchers is a good haul.

These deals were a lot more exciting at the time than they are looking back on them now. Sometimes prospects just don’t work out. If anything, seeing players like Moss and Bautista succeed elsewhere indicates they had a lot more trouble developing young hitters at this time.

There at least was a clear plan in place: trade their best major leaguers for other team’s best minor leaguers. That won’t always be the case the next two years.

Alex Stumpf

Alex is a credentialed Pirates beat reporter with The Pittsburgh Sports Report. If you want to keep up to date on the team or have a story idea, you can follow or reach him @AlexJStumpf.