Top Five worst trades in Pittsburgh Pirates history

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

Baseball is a game of ebbs and flows. You see this over the course of 162 games. You win games you should lose and you lose games you should win. The Trade Deadline is a microcosm of the game itself. You see teams make good trades and bad trades. Heck sometimes you see the dreaded salary dumps. The Pittsburgh Pirates are like every other team in sports. Throughout their history they have made many franchise altering trades and in that same time they’ve made trades I am sure they regret. Today I am going to list the top 5 worst trades in Pittsburgh Pirates history. What makes a trade bad? A variety of factors go into bad trades, but to me a bad trade is one where the player or players you traded were way more successful than the players you got back in return. So, without further ado, I present you to you, the top 5 worst trades in Pittsburgh Pirates history…

Next: Number 5

Jul 11, 2015; Kansas City, MO, USA; Kansas City Royals pitcher Chris Young (32) delivers a pitch against the Toronto Blue Jays during the first inning at Kauffman Stadium. Mandatory Credit: Peter G. Aiken-USA TODAY Sports

1. December 20, 2002: Chris Young and Jon Searles traded to the Montreal Expos for Matt Herges.

Chris Young never appeared in a game with the Pittsburgh Pirates, but his trade still makes no sense. He was a young prospect with a fantastic arm and appeared to have ridiculously high potential, but out of no where in December of 2002, he was traded for Matt Herges of the Montral Expos. Herges, like Young also never appeared in a game with the Pittsburgh Pirates as three months after the trade, he was given his outright release by the organization.

Chris Young would go on to become a very productive big league pitcher. To date he’s pitched 11 big league seasons and compiled a 73-58 record with a 3.73ERA, a 4.40FIP, an ERA+ of 108 and accumulated 17.3 WAR.

This is one of the most annoying moves of the Littlefield Era. He traded a young, cost controlled starting pitcher for a guy that ended up released three months after the deal. The salt in the wound of this trade is that in 2003 Herges would sign with the San Diego Padres, appear in 40 games with an ERA of 2.86, a FIP of 3.30 an ERA+ of 139. He would then be traded to the Giants and continue his stellar season. Pitching a 2.31ERA, a FIP of 2.66 and an ERA+ of 186 with San Francisco.

Dave Littlefield wasn’t alone in making some bizarre and bad trades, heck even World Series winning management teams can make some boneheaded deals. Which brings us to number three on our list…

Next: Number 3

Jul 25, 2015; Cooperstown, NY, USA; Hall of Famer Bert Blyleven waves as he and wife arrive at National Baseball Hall of Fame. Mandatory Credit: Gregory J. Fisher-USA TODAY Sports

1. December 9, 1980: Bert Blyeven and Manny Sanguillen traded to the Cleveland Indians for Gary Alexander, Victor Cruz, Bob Owchinko and Rafael Vasquez.

The Pirates were only one season removed from the “We Are Family” World Series winning team, but you could see it was about to be a down swing for the team as they they sent away World Series heros, Bert Blyleven and Manny Sanguillen to the Cleveland Indians for a very minimal return.

Bert Blyleven only spent three seasons with the Pirates, but in that time he was a front line, albeit inconsistent starting pitcher. He went 34-28 with a 3.47ERA, a 3.26FIP, an ERA+ of 109 and was worth 9.9WAR. After being traded from the Pirates, Blyleven continued his winning ways and eventually became an Hall of Fame pitcher with a record of 287-250 an ERA of 3.31, a FIP of 3.19, an ERA+ of 118 and was worth 96.5WAR.

Manny Sanguillen despite being involved in this trade, never appeared in a game for the Cleveland Indians, so he really doesn’t factor much in this being one of the worst trades in Pirates history.

The return for this trade was very mediocre as none of the players really turned into anything special for the Pirates.

Gary Alexander spent one very mediocre season with the Pirates where he hit .213/.255/.404/.659/82OPS+.

Victor Cruz had a successful but very brief season with the Pirates before being traded to the Texas Rangers in 1982. In his one Pirates season he appeared in only 22 games, but pitched to a 2.65ERA, 4.66FIP, an ERA+ of 139 and was worth 1.4WAR.

Bob Owchinko did not appear in a game with the Pirates as a part of this trade as he was traded to the Oakland Athletics for Ernie Camacho and cash. He did however, rejoin the team in the 1983 season, appeared in one game and pitched to an infinity ERA.

Rafael Vásquez never appeared in a game with the Pirates. He spent the 1981in Double-A and pitched to a 4-8 record with a 3.98ERA and a WHIP of 1.408 before retiring following the season.

When you trade a player that eventually becomes a Hall of Famer and the return is as paltry as this one it automatically becomes a huge loss for the Pirates. Only Victor Cruz made any impact with the Pirates and he only pitched one season with the team. With returns like this, it’s no wonder the Pirates went from World Series Champions in 1979 to one of the worst teams in the league by the mid 1980s.

As bad as the 1980s Pirates were, they do not compare to the Pirates of the 1940s and 50s, who’s only draw was a home run hitting outfielder until they sent their only draw packing. Which brings us to number two on the worst trades list…

Next: Number 3

Jun 29, 2014; Pittsburgh, PA, USA; Detail view of a commemorative patch worn on the New York Mets uniforms to honor Mets former broadcaster Ralph Kiner during the game against the Pittsburgh Pirates in the eighth inning at PNC Park. The Pirates won 5-2. Mandatory Credit: Charles LeClaire-USA TODAY Sports

1. June 4, 1953: Ralph Kiner, Joe Garagiola, George Metkovich and Howie Pollet traded to the Chicago Cubs for Bob Addis, Toby Atwell, George Freese, Gene Hermanski, Bob Schultz, Preston Ward and $150,000.

The Pirates of the 1940s and early 1950s were absolutely terrible. They had one draw and that draw was Ralph Kiner. He was a monster in his eight seasons with the Pirates, hitting 301 home runs and slashing .280/.405/.567/.971/OPS+149 and was worth 44.5WAR. Despite all of Kiner’s home runs, the team continued to be terrible and 41 games into the 1952 season, Kiner along with Joe Garagiola, George Metkovich and Howie Pollet were traded to the Chicago Cubs. Kiner actually never really saw success after the trade, playing only two more seasons, but his trade is included because of what it represented to the franchise at the time. Kiner was THE super star on the Pirates and to see him sent away mostly because of money issues really sent a bad message to the fan base. Kiner along with the other players traded really told their fans that the Pirates weren’t going to be winning any time soon. Joe Garagiola, George Metkovich and Howie Pollet were not super stars by any means, but they were all steady and consistent players with the Bucs.

Joe Garagiola spent parts of three seasons with the Pirates and in that time he was a very steady producer. Slashing .262/.362/.417/.778/110OPS+ and was worth 4.5WAR. After the trade he never really approached those numbers

George Metkovich also spent three seasons with the Pirates and in that time was an almost league average offensive player. In his time with the Pirates he hit .276/.333/.379/.711/92OPS+ and accumulated 2.0WAR. After being traded he only played two more Major League seasons and was mostly unimpressive.

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Howie Pollet was probably the easiest player to trade as his Pirates career was very underwhelming. In his four seasons with the Pirates he pitched to a 14-31 record with a 4.59ERA, a 4.47FIP and an ERA+ of 88. He was actually much better after the trade, pitching to a 4.19ERA, 3.76FIP and an ERA+ of 102 in three seasons with the Chicago Cubs.

The theme in all disappointing trades is the return is almost always terrible and the Kiner trade is no different. Bob Addis, Toby Atwell, George Freese, Gene Hermanski, Bob Schultz, Preston Ward were all very poor players for the Pirates and because they were traded for the Pirates franchise player, it’s especially bad. They never had a chance to live up to the legacy that was Ralph Kiner.

Bob Addis only appeared in three games for the Pirates in 1953 and never recorded hit in his three at-bats.

Toby Atwell spent four very mediocre seasons with the Pirates and his numbers were not pretty even by catchers’ standards. In his four seasons he put up a .250/.356/.315/.671/80OPS+.

George Freese spent one season with the Pirates and it was not a very strong one. He managed to hit a very pedestrian .257/.327/.374/701/88OPS+ and hit only three home runs and drove in 22.

Gene Hermanski played in only 41 games with the Pirates and in those 41 games he did nothing to impress the team or its angry fan base. Hitting a horrible .177/.282/.226/.507/35OPS+. He was released after the season and promptly retired.

Bob Schultz only appeared in 11 games for the Pirates and posted an 8.20ERA, a 6.08FIP and an ERA+ of 25. He then missed the entire 1954 season with an injury before being traded to the Detroit Tigers .

Preston Ward was probably the most successful piece in the Kiner trade, which is a testament to just how bad the trade was. In his four seasons with the Pirates, Ward hit .240/.326/.368/.694/83OPS+. He also hit 21 home runs as a member of the Pirates.

While Ralph Kiner never really found success after being traded from Pittsburgh, the laughably bad return still makes this one of the worst trades in Pirates history. The team traded a home run hitting superstar and only managed to get back mediocre players at best and dreaful players at worst, but I’ll bet that $150,000 felt really good to a team struggling to draw a crowd after the trading of Kiner.

The Kiner trade was a salary dump, pure and simple and those kind of trades usually end in disaster. Which brings us to the number one worst trade in Pirates history…

Next: Number 1 worst trade in Pirates history is...

Jun 28, 2015; Milwaukee, WI, USA; Milwaukee Brewers third baseman Aramis Ramirez (16) hits a double in the seventh inning during the game against the Minnesota Twins at Miller Park. Mandatory Credit: Benny Sieu-USA TODAY Sports

1. July 23, 2003: Aramis Ramirez and Kenny Lofton and cash to the Chicago Cubs for Matt Bruback, Jose Hernandez and Bobby Hill.

We’ve kind of come full circle on this trade with the recent acquisition of Aramis Ramirez, but that doesn’t undo just how absolutely dreadful this trade was. Ramirez was the top prospect of the Pittsburgh Pirates when he was called up in 1998 and from then until the trade he was a very steady player for the Buccos. In that time he hit 76 home runs and slashed .262/.311/.434/.746/90OPS+ and was worth 1.1WAR after the trade to Chicago, Ramirez blew up and became one of the league’s best players. From 2003 until 2011 he slugged 239 home runs and hit .294/.356/.531/.887/126OPS+ and was worth 23.8WAR.

Kenny Lofton was an already well established player by the time he got to the Pirates. Him being traded wasn’t a huge surprise, but being included in this trade seemed completely out of no where. He wasn’t anything overly special with the Pirates in his half season with the team, but he was productive. He slashed .277/.333/.437/.770/98OPS+ and accumulated 1.6WAR. After being traded to Chicago his numbers all increased and he helped the Cubs win the NL Central and come within a Bartman’s hand of the World Series. He hit .327/.381/.471/120OPS+ and was worth 1.8WAR.

Like all truly bad trades, the return on this one is hilariously pathetic. None of the players involved were with the organization by the end of the 2005 season. So this trade was a failure within two seasons and that isn’t easy to pull off. The center piece of the trade was Bobby Hill, which is basically the punchline of a horrible joke. In parts of three seasons with the Pirates, the man Dave Littlefield said “change fans opinion of the trade” hit .267/.352/.337/.689/83OPS+ and ended up worth 0.2WAR. He only played in 185 games with the Pirates and was DFA’d in the middle of the 2005 season. He never again appeared in the Major Leagues.

Jose Hernandez was already a veteran of 13 Big League seasons by the time he got to the Pirates in this trade and it still makes no sense why Dave Littlefield would send a young in prime third baseman to a division rival for a 33-year-old infielder. Heck his career wasn’t exactly impressive before he got to the Pirates. He was a below average player when he was in his prime. In his 125 games with the Pirates, he hit five home runs and slashed .240/.299/.335/.635/64OPS+ and was worth -0.1WAR.

Matt Bruback never appeared in a game for the Pirates and was out of the system by the end of the 2003 season. In his one Triple-A season in the organization he went 2-2 with a 4.91ERA and a WHIP of 1.364. He never made Major Leagues and eventually retired after the 2006 season with the Baltimore Orioles organization.

This trade still leaves a bitter taste in a lot of people’s mouths for a variety of reasons. It was another bad move by maybe the worst GM in Pittsburgh sports history and because he sent Ramirez away to a division rival, Pittsburgh fans had to watch as he developed into one of the league’s most feared sluggers and seemingly tormented the Pirates every single time he played against the team.

Next: Final Thoughts

Aug 12, 2014; Pittsburgh, PA, USA; Fans begin to arrive as rain falls before the Pittsburgh Pirates host the Detroit Tigers in an interleague game at PNC Park. Mandatory Credit: Charles LeClaire-USA TODAY Sports

The Pirates have a rich and storied history that many teams would kill for, but in that time they’ve also made plenty of terrible trades. These five are ones that stick out to me because they all represent very low points in franchise history. 2001 Pirates were a mess of a baseball team and exceptionally difficult to watch. 2002-2003 were the lowest of the low during the 20-year losing streak because the team was awful without a plan. The 1950s Pirates were just the worst time in the history of the organization. The 1980s were a down swing coming off one of the most successful decades in franchise history.

There were other factors that contributed to these bad periods of baseball, these deals to me show how bad trades can set a franchise back for a long, long time. Especially when the players involved not only don’t pan out, but are also monumental busts for your team. It’s one thing to trade for one bad player, but to trade for a series of awful players is really damaging. It’s the kind of thing that kills fan interest and gets general managers fired. I am sure there are other trades that I forgot to mention, but these are my top (or bottom) five worst trades in Pirates history.

Next: Pittsburgh Pirates may have a bullpen answer in John Holdzkom