Pittsburgh Pirates Trade History: The Boston Red Sox Edition

It’s time for part #14 in our Pittsburgh Pirates Trade History series, looking at all of the qualified trades between the Pirates and all of the other big league franchises. Today’s article looks at the Boston Red Sox, a team that went a long time before they made a qualified trade with the Pirates.

You might be new to this series and wonder what a “qualified trade” means exactly. If I looked at every transaction between two teams, I’d be here forever. What I deal with here are the trades that involved players from both sides and at least one of those players had to play in the majors, either before and/or after the trade. That means no waiver claims, player purchases, Rule 5 picks or trades that involved only players who were in the minors for their entire careers.

Despite being Major League teams together for 120 seasons now, the Pirates and Red Sox have only made ten trades. It’s really 12 trades total, but two of them have a part A and B, so we will make them into ten below. We start with the oldest one first.

From 1901 until November 19, 1962, the Pirates and Red Sox only had player purchase transactions between them (six total) and none of them were that significant. That streak was snapped on November 20, 1962 when the Pirates sent first baseman Dick Stuart and pitcher Jack Lamabe to Boston for catcher Jim Pagliaroni and pitcher Don Schwall. Stuart was the big name here and he put up some big power numbers in Boston, but the Pirates made out in the end. Lamabe was a rookie pitcher for the 1962 Pirates, who did well in the relief role. He had a decent first season in Boston, but they tried him as a starter in 1964 and things did not go well. He ended up with a 4.88 ERA in 354 innings in Boston over three seasons. He had 2.7 WAR total in his first two seasons, then compiled -2.2 WAR over the rest of his seven-year career. Schwall had a great rookie season in 1961, then struggled the next year. The Pirates got four seasons out of him, with a 3.24 ERA in 336 innings, before he was dealt even up for veteran pitcher Billy O’Dell. The Pirates took a small victory in the pitching part of this trade, but the batters were the significant part.

Stuart hit .273 with 117 homers in five seasons with the Pirates. He had a huge season in 1961, then dropped off in 1962, so the Pirates were selling low on him. He hit 42 homers and drove in 118 runs (led the AL) during his first season in Boston, then hit 33 homers and picked up 114 RBIs in his second season.  He was traded for a decent starting pitcher named Dennis Bennett after the 1964 season. Obviously Fenway Park was a much better park for offense than the spacious Forbes Field, so that accounts for some of the numbers. Despite doing well, Stuart was still painful to watch on defense and it really affected his overall value. He put up just 2.3 WAR with Boston and -0.1 WAR in the four years that followed. The Pirates had Pagliaroni for five years. He spent two years in a platoon role, two as the starter, and one as a backup. He hit .254 with 49 homers and 185 RBIs and played above average defense. Pagliaroni was worth 9.6 WAR for the Pirates before they sold him to the Oakland A’s. The Pirates took the easy win here with the better position player and better pitcher.

The 1962 trade didn’t kick-start anything between these two clubs. They went another 16 1/2 years before the second trade and it too was an important one. The Pirates sent two minor league lifers in George Hill and Martin Rivas, plus cash, to the Red Sox for Mike Easler. Looks like a clear win here, but I can’t forget the reason that they traded for Easler. Five months before this trade, the Pirates sold Easler to Boston. Basically, this trade was two minor league players sent to Boston for nothing, but if you forget the first part, then the Pirates made out great here. They got 7.6 WAR from Easler for five seasons before trading him for a strong starting pitcher….

In December of 1983, the Pirates sent Easler back to Boston for pitcher John Tudor. It was a bit of an odd deal for the Pirates at the time because they seemed deeper in the pitching ranks and already had some holes to fill on offense. Easler had a strong first season in Boston, then saw a drop in production in 1985, which led to a trade to the New York Yankees for Don Baylor. The Pirates got some nice pitching out of Tudor, who went 12-11, 3.27 in 32 starts and 212 innings. However, they counteracted that good by trading Tudor for outfielder George Hendrick. They were smart enough to see that getting Hendrick was a mistake and got rid of him in early August of his first season with the team, so they didn’t take the full brunt of that bad trade. The California Angels were saddled with four years of a bad contract that amounted to -0.5 WAR for them. However, Tudor put up some big seasons with the St Louis Cardinals so the Pirates could have finished with a big win here if they held on to him. You have to give a slight edge to the Red Sox in the Tudor/Easler deal, but not enough to call it a loss for the Pirates.

The next trade was the first of two trades that had two parts, and this one was much more significant than the other one. On July 22, 2003, the Pirates sent relievers Mike Gonzalez and Scott Sauerbeck to Boston for pitchers Brandon Lyon and Anastacio Martinez. Lyon had an injury, so he was sent back to Boston on July 31st, along with Martinez, while the Pirates got Gonzalez back. Also included in part two were Jeff Suppan going to Boston and Freddy Sanchez and cash going to Pittsburgh. So the two deals made nine days apart amounted to Sauerbeck and Suppan for Sanchez and cash, and we can ignore everything else. Clearly the Pirates took the win here. Sanchez became an All-Star, while the Red Sox paid decent money to a pair of two-month rentals, who both got roughed up. They combined for 0.0 WAR, while Sanchez put up 13.2 WAR in his five full seasons in Pittsburgh. The cash part did better in the deal than Suppan and Sauebeck.

The next deal was a three-part deal made in July of 2008, so it’s a bit tougher to judge a winner between just two clubs when a third club was involved with both teams. The Pirates sent Jason Bay to Boston and Boston sent Manny Ramirez to the Los Angeles Dodgers. The Pirates received pitcher Craig Hansen and outfielder Brandon Moss from the Red Sox, and Bryan Morris and Andy LaRoche from the Dodgers. You could say that the Pirates did a 4-for-1 deal here, but it didn’t all come from the Red Sox. Bay put up 7.2 WAR for the Red Sox in one full season and two months, then lost him via free agency, so that’s basically what the Pirates lost here, other than almost $10M remaining in salary. The reason you can’t give Boston a win is because Ramirez did even better than Bay in 2008, then had a decent (low for him) year in 2009, so they didn’t really get much better. They also gave up two prospects who had some value at the time, though we all know that didn’t work out for the Pirates.

The Pirates really only saw Morris do well after the deal and everyone else disappointed, though Hansen was injury related and not performance, because he was basically injured the whole time. Even Morris only saw a small bit of success with the Pirates before they traded him away, then he did better after the trade. LaRoche and Moss both had potential to help the offense, and Moss did perform well later in his career, but it took him time to get on track. LaRoche never got on track. The real winner in this deal was the Dodgers, who got Ramirez for two prospects, but the Red Sox obviously did better than the Pirates too, so for grading sake, we will give them the win here. Pirates got 0.3 WAR each from both LaRoche and Morris, while Moss and Hansen both put up negative numbers.

A year after that three-team trade, the Pirates sent first baseman Adam LaRoche to the Red Sox for minor league shortstop Argenis Diaz and minor league pitcher Hunter Strickland. Nine days later, LaRoche was traded to the Atlanta Braves for Casey Kotchman, who then got traded in the off-season for veteran Bill Hall. The Pirates were giving up two months of LaRoche for two prospects, and he wasn’t going to do anything in those two months to help the 2009 Pirates. The Pirates got 22 big league games out of Diaz in 2010. He has contributed more to them in the last few years as a minor league infield instructor, but we can’t count that as part of the trade. Strickland was lost on waivers in 2013, after being sidetracked by injuries. He eventually made the majors in and had some good seasons in middle relief from 2015 to 2018. His playoff record has been awful (nine homers in 13 innings!) but he helped get his teams there in the first place. None of that helps the Pirates though, so it was basically two months of LaRoche for 22 games of Diaz and a small amount of cash (waiver claims cost money). Can’t really give Boston a win here, LaRoche played six games and then Kotchman played poorly, but the Pirates didn’t get much here for their big trade piece.

The second trade with two parts was a very minor one both times. The Pirates sent minor league outfielder Jonathan Van Every to Boston for a player to be named later, only to get Van Every back five weeks later for a low-level minor league catcher named Josue Peley. Van Every was released by Boston in 2009 and signed with the Pirates, so in a matter of ten months total, he went from Boston to Pittsburgh to Boston to Pittsburgh. He played 22 games for the Red Sox after the trade and hit .211, mostly as a bench player. The Pirates had him in Triple-A all year and they never actually received a player to be named later, so it was either a cash deal or the second deal nullified that part. He had 0.0 WAR in Boston and Peley was never considered to be a prospect, so this paragraph is a lot of words to say these two trades amounted to nothing.

On November 28, 2012, the Pirates acquired pitcher Zach Stewart for a player to be named later, which turned out to be minor league pitcher Kyle Kaminska. Stewart was lost of waivers two months later, Kaminska never pitched in the majors, so nobody won here.

Finally, we get to a big deal made just a month after the previous trade. The Pirates sent Joel Hanrahan to Boston for Mark Melancon, Stolmy Pimentel, Jerry Sands and Ivan DeJesus. The Pirates got great production out of Melancon here and Hanrahan did very little for Boston, but this wasn’t a one-sided deal. The three prospects the Pirates received all had some potential that never amounted to anything of note. Pimentel pitched 25 games in relief for the 2013-14 Pirates before being lost on waivers to the Texas Rangers. DeJesus reached minor league free agency after the 2013 season and never played for the Pirates. Jerry Sands was lost on waivers after the 2013 season and never played for the Pirates. Hanrahan did poorly in nine games for the Red Sox and then was injured the rest of the season. Those four players basically washed each other out, though the Red Sox paid $7M to get their -0.5 WAR.

Melancon was a three-time All-Star in his four years with the Pirates before being dealt to the Washington Nationals. He was their closer during the three-year playoff run. That was great production, but Holt, who seemed like the throw-in, became a valuable utility player for the Red Sox. He had 8.5 WAR in seven seasons with Boston, compared to 8.0 WAR for Melancon during his time in Pittsburgh. This is still a win for the Pirates, but it’s not as one-sided as some people think.

So we have some decent results here for the Pirates, with the best trades turning out to be the first one and the Sanchez deal. They won the Melancon trade, and if you want to give them the first Easler trade too, then feel free. In my opinion, that was just them correcting a mistake made months earlier, so I don’t like giving a win there. The loss would be the Bay deal. The Tudor deal turned out bad, but that was because of the subsequent trade only. The Red Sox portion was fine, and could have been a big win if they held on to Tudor longer.