Top 5 Best Trades in Pittsburgh Pirates History

Mar 5, 2015; Bradenton, FL, USA; A general view of the Pittsburgh Pirates during batting practice before the game against the New York Yankees at a spring training baseball game at McKechnie Field. Mandatory Credit: Kim Klement-USA TODAY Sports

From 1993 through 2012, the Pittsburgh Pirates were always sellers at the trade deadline. For the better part of 20 years, the trade deadline was simply a time when Pirates fans said goodbye to their good players and wished them well with their new teams. The Pirates have an extremely mixed history with trades. They’ve made some inexcusably horrible trades through out their history, but like baseball itself, trades are a game of ebbs and flows. For every bad Pirates trade there is a good one. Today I am going to discuss the all time top 5 best Pirates trades of all time. I gage a good trade by how it impacted the Pirates at the time of the trade and how it impacted the Pirates in the future. I also measure what the Pirates got compared to what they gave up.

So, without further ado…

Next: Number 5

Mar 13, 2015; Bradenton, FL, USA; A general view of McKechnie Field during the fourth inning of the game between the Minnesota Twins and Pittsburgh Pirates . Mandatory Credit: Tommy Gilligan-USA TODAY Sports

1. Aug. 26, 2003 — Pirates receive Jason Bay, Oliver Perez and Corey Stewart from the Padres for Brian Giles.

Brian Giles was an immensely popular player in his time in Pittsburgh and I am sure many fans were angry when he was traded to the Padres mid 2003, especially for a couple of relative unknowns. Corey Stewart never appeared in a game with the Pirates during his two seasons with the organization, but Jason Bay and Oliver Perez were huge pieces for the Pirates during their tenures.

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Jason Bay in particular was the Pirates franchise player during his time with the organization. In his six seasons with the Pirates from 2003 until 2008, Bay slashed .281/.375/.515/.890/131OPS+ and accumulated 15.0WAR.

Oliver Perez was the other main piece in this trade and while he was wildly inconsistent, you cannot deny that for a couple seasons he was one of the most electric pitchers in all of baseball when he was on. His 2004 season alone was worth the price of admission. He went 12-10 with a 2.98ERA. In addition to his stellar ERA, he lead the league in strikeouts per inning with 11, struck out 239 batters and had an ERA+ of 143.

Brian Giles was an absolute machine with the Pirates from 1999-2003. In his time with the Pirates he hit 165 home runs and slashed .308/.426/.591/1.018/158OPS+ He also accumulated 26.0WAR as a member of the Pirates. After the trade, Giles continued to be a solid player with the Padres, but was not nearly as dynamic as he was with the Pirates. In his career with San Diego he hit 83 home runs and slashed .279/.380/.435/.815OPS/122OPS+ and was worth 17.3WAR.

Jason Bay alone was worth more with the Pirates than Brian Giles with the Padres, but couple his WAR with Oliver Perez’s 4.2WAR and it isn’t even close, this is a very clear victory for the Pirates.

We now go to number four on the all time great Pirates trades…

Next: Number 4

Oct 7, 2013; Pittsburgh, PA, USA; Pittsburgh Pirates right fielder Marlon Byrrrd (2) reacts after being called out on strikes against the St. Louis Cardinals during the second inning in game four of the National League divisional series at PNC Park. The St. Louis Cardinals won 2-1. Mandatory Credit: Charles LeClaire-USA TODAY Sports

1. August 27, 2013: Pirates receive Marlon Byrd and John Buck from the Mets for Dilson Herrera and Vic Black.

2013 was a magical season for the Pirates. Coming off back to back collapses, many were weary of the contending Pirates, but they silenced a lot of doubters by winning 94 games and an incredible NL Wildcard game. The Pirates right field production for most of 2013 left a lot to be desired, which is why the addition of Byrd was so pivotal for the team. While his tenure with the Pirates was short, he was a huge contributor to the first Pirates playoff team since 1992. John Buck was mostly a throw in for the Pirates, but honestly Byrd alone makes this trade a win for the Pirates.

Marlon Byrd only played 30 regular season games for the Pirates, but from game one, it was clear he was going to help carry the Pirates into the post season. He homered in his first game with the Pirates and kept hitting from there. In his short time with the Pirates he hit three home runs and slashed .318/.357/.486/.843/137OPS+. He also kick started the 2013 NL Wildcard game by homering in the second inning, igniting the crowd and setting up the now famous “Cueto Cueto Cueto.”

John Buck was a back up catcher and really didn’t play much for the Pirates. He played in nine games with the team, so really his contributions don’t factor in much in this trade, but he was involved and did a solid job, albeit a very brief job.

The Pirates gave up two very solid prospects to land Byrd and Buck. Dilson Herrera is likely the Mets starting second baseman of the future and Vic Black has a big arm and has been solid in his brief time with the Mets. The jury is still out on this trade from the Mets perspective, but for the Pirates, they got the right fielder they needed for a playoff run and that is about as good as it gets from a rental player.

2013 was the first playoff run for the Pirates since 1992 when the Pirates won their third straight NL East title, while this man wasn’t there in 1992, he was a huge piece of the 1990 and 1991 teams. Number two on our list is…

Next: Number 2

Mar 21, 2014; Tampa, FL, USA; Pittsburgh Pirates helmets and bats lay in the dugout prior to the game against the New York Yankees at George M. Steinbrenner Field. Mandatory Credit: Kim Klement-USA TODAY Sports

1. July 23, 1986 — Pirates receive Bobby Bonilla from the White Sox for Jose DeLeon.

Before signing the world’s greatest contract with the New York Mets, Bobby Bonilla was part of the original outfield of dreams with the Pirates. Along with Barry Bonds and Andy Van Slyke, Bonilla was part of maybe the greatest outfield in Pirates history and a huge piece of the Pirates return to glory in the early 90s. In his six seasons with the Pirates, Bonilla mashed 114 home runs and slashed .284/.357/.481/.838/134OPS+ and he was worth 20.3WAR.

Jose DeLeon was a fairly solid pitcher with the Pirates. From 1983 until 1986 he went 17-38 with a 4.02ERA and a 3.39FIP. He was basically a slightly below league average pitcher while in Pittsburgh. He actually saw a slight increase in his numbers while with the White Sox. His first season with the White Sox was very solid. He went 4-5 with a 2.96ERA and a 3.95FIP and in his second season, he regressed to his FIP. Going 11-12 with a 4.02ERA and a 4.46FIP. He was traded away from the White Sox after the 1987 season, while Bonilla mature into one of the game’s best hitters. This trade is a clear and huge win the Pirates.

Bobby Bonilla wasn’t the only contributor of the early 90s Pirates teams acquired via trade. Another huge piece was traded for only one season later. Which brings us to our number one trade in Pirates history…

Next: Number 1

Jun 8, 2014; Pittsburgh, PA, USA; The Milwaukee Brewers bats rest in the rack prior to the game against the Pittsburgh Pirates at PNC Park. Mandatory Credit: Charles LeClaire-USA TODAY Sports

1. April 1, 1987 — Pirates receive Andy Van Slyke, Mike LaValliere and Mike Dunne from the Cardinals for Tony Pena.

To most early 90s Pirates fans, Barry Bonds was clearly the best player on the team, but Andy Van Slyke was easily the most popular. He was a young, good looking Center Fielder and he represented the Pirates saying goodbye to the mid to late 80s, where the team was awful and hello to one of the greatest runs in franchise history. Van Slyke wasn’t just ceremonial, he was also wickedly talented. In his eight years in Pittsburgh, he hit 114 home runs and put together a line of .283/.353/.458/.811/.124OPS+ and was worth 30.9WAR.

Andy Van Slyke wasn’t the only player acquired in this trade as Mike LaValliere was also a big piece to the Pirates division titles of 1990, 1991 and 1992. He wasn’t an offensive juggernaut by any means, but his numbers from the catcher position were more than respectable. In his seven years with the Pirates, Spanky hit .278/.363/.351/.714/102OPS+ and also won a Gold Glove in 1987 when he threw out 45 percent of would be base stealers. In his time with the Pirates, he was above league average in caught stealing in four of his seven seasons.

Mike Dunne didn’t contribute to the NL East division winners of the 1990s, but he was a solid pitcher in his three seasons with the Pirates. Going 21-18 with a 3.65ERA and a 4.43FIP. He also finished second in Rookie of the Year voting in 1987.

Tony Pena was a very good catcher in his seven seasons in Pittsburgh before the trade. He hit .286/.327/.411/.738/104OPS+. He was also a six time All Star and a four time Gold Glove winner with the Pirates. He was still a fairly solid player with the Cardinals, helping them reach the World Series in 1987. His numbers however were down while in St. Louis, he hit .248/.303/.342/.645/79OPS+. There’s also no comparing his value to LaValliere’s and Van Slykes. Pena was worth 2.2WAR with the Cardinals, while in the same time, Van Slyke alone was worth 15.3WAR. Pena did rebound and put up some solid seasons in Boston, but Van Slyke by himself makes this trade a win for the Pirates. Throw in Mike LaValliere and it’s pretty obvious that the Pirates hosed the Cardinals in this deal.

Next: Final Thoughts

Sep 18, 2014; Pittsburgh, PA, USA; Pittsburgh Pirates general manager Neal Huntington (left) talks with Boston Red Sox general manager Ben Cherington (right) on the field before the Pirates host the Red Sox at PNC Park. Mandatory Credit: Charles LeClaire-USA TODAY Sports

The Pirates have been around since 1887 and in that time they’ve made some bad trades and of course some good ones. This list makes up five of the best in my opinion, not the only great trades in franchise history and I am sure it will cause some debate. I am sure I’ve forgotten some other vital trades, but to me these five deals are pivotal because they were all franchise altering or caused a hugely memorable moment as a result of the deal.

Trades are always so thrilling because they represent change and change can be either exciting or scary depending on where your team is in the standings. I do know one thing for sure, being buyers is way more thrilling than being sellers. However, you cannot ignore some of the important trades the Pirates made while being sellers. The saving grace of being sellers is that you never know which trade ends up helping turn your team go from losers to winners. You may trade a hugely popular player that lands you some major pieces to division winning teams or a rental that helps your team return to glory from the abyss of a 20 year losing streak.

Next: The 12 Days of Trademas - Day 5 - Mitch Moreland