I was originally going to title this the St Louis Browns/Baltimore Orioles trade edition. For those who don’t know, the Baltimore Orioles franchise was in St Louis and known as the Browns until the 1954 season. To be more complete with their history, they were the Milwaukee Brewers in 1901, then moved to St Louis in 1902. I didn’t think that the Pirates and Brewers made any deals during that 1901 season, but they had 52 years to make a trade with the Browns, so it seemed like they should have got in at least one or two during that time.
As I mentioned with the Detroit Tigers and Cleveland Indians editions of this series, American League and National League teams didn’t make many trades in the early years (1901-50), so that’s why I had low expectations for the amount of trades with the Browns. For this article, we only cover transactions that involved at least one player going each way and at least one of those players had to have Major League experience, either before or after the trade. The Pirates and Browns made six transactions in 52 seasons (53 if you count the Milwaukee year) and all of them were player purchases. So our St Louis Browns/Baltimore Orioles trade edition became just the Orioles and our first deal happened in 1954.
On May 25, 1954, the Pirates sent veteran outfielder Cal Abrams to the Orioles for pitcher Dick Littlefield. Abrams was struggling with the Pirates, but he turned things around in Baltimore and put up a 3.9 WAR over the rest of the season. He followed that up with a solid 1955, then the Orioles dealt him away at the perfect time. He played just four more big league games after the trade. Littlefield lasted with the Pirates until 1956. He went 15-23, 4.29 in 297.2 innings, making 40 starts and 24 relief appearances. His true value to the Pirates was in a different trade, as he helped them acquire Bill Virdon in a one-sided deal.
The next trade didn’t happen for 9 1/2 years, when the Pirates sent Harvey Haddix to Baltimore for minor league shortstop Richard Yencha and cash. Yencha did well in 1963 at 21 years old in A-ball, but he never made the majors. Haddix was a solid reliever in two seasons with the Orioles, posting a 2.63 ERA in 123.1 innings, before being released over the 1965-66 winter, which ended his big league career.
Five years later, the two teams hooked up on a four-player deal that went nowhere. The Pirates got minor league catcher Del Bates and minor league infielder Ed Pacheco in exchange for minor league infielders Jack Damaska and David Heintz. Bates was the only one who played in the majors after the deal, seeing brief time with the Philadelphia Phillies in 1970. Damaska was the only one with prior big league time, briefly playing for the 1963 St Louis Cardinals. Bates was traded by the Pirates to the Phillies for two players who never played in the majors after the deal.
The two clubs went another 19 years before making the fourth trade. They picked up the pace a bit since this deal, but they had just three trades in the first 86 years of the Brewers/Browns/Orioles existence.
In November of 1987, the Pirates sent outfielder Joe Orsulak to the Orioles for minor league infielders Terry Crowley and Rico Rossy. The Pirates went for upside and missed. Crowley was drafted out of high school a year before this deal. He never made the majors. Rossy made the majors, but not before the Pirates traded him away for minor leaguer Greg Tubbs, who never played in Pittsburgh. The Orioles won this deal fairly easy, with Orsulak being a solid contributor for five seasons, compiling an 8.0 WAR during that time.
The two teams didn’t wait long for the next deal and it was another one-sided loss for the Pirates. On November 9, 1988, the Pirates gave up first baseman Randy Milligan for minor league pitcher Pete Blohm. Milligan put up 11.1 WAR over the next four seasons in Baltimore and Blohm never made the majors. While the Pirates still made the playoffs three straight years, it would have been nice to get something of value back for two players who were solid contributors in Baltimore at that same time.
In the middle of the 1989 season, the Pirates traded minor league infielder Tony Chance for pitcher Mike Smith, who had four cups of coffee in the majors, but could never stick. He put together a decent 24 innings for the 1989 Pirates, but that’s all they got from him. He was released after the season. Chance never made the majors, so it’s a very minor victory for the Pirates after two trades that worked out poorly.
While making a playoff run in September of 1990, the Pirates acquired pitcher Jay Tibbs for pitcher Dorn Taylor. Tibbs made five appearances, allowing two runs in seven innings. He became a free agent after the season, but served his purpose. Taylor had minimal big league time already and after the deal he made four relief appearances for the 1990 Orioles. So the Pirates didn’t give up much for their rental player.
In March of 1991, the Pirates could claim victory in a deal that saw them get a minor league player who never appeared in the majors. They gave up minor league infielder Tommy Shields for minor league infielder Tony Beasley, Shields hit .176 in 22 big league games, two coming with the Orioles. Beasley became a coach for the Pirates after spending seven years in their system. He managed Pirates affiliates to five straight playoff appearances (2001-05) and won two league titles.
In September of 1993, the Pirates sent outfielder Lonnie Smith to the Orioles for minor leaguers Stan Cameron and Terry Farrar. Neither of those players made the majors, but the Pirates were giving up Smith for the final three weeks of a season that was already lost to them. Smith played just nine games in 1993, though he re-signed with Baltimore as a free agent in 1994.
After a flurry of deals, the two clubs went 19 years before the Derrek Lee for Aaron Baker deal. Lee crushed the ball with the Pirates for 28 games before getting injured, in what ended up being his last big league season. The Pirates tried to sign him for 2012, but he retired instead. Baker never made the majors.
A year later, the Pirates got infielder Yamaico Navarro for minor league pitcher Jhondaniel Medina. Navarro struggled in 29 games with the Pirates, hitting .160, before ending up back with the Orioles for his final eight big league games. Medina never made the majors.
In an asterisk deal here, the Pirates got outfielder Russ Canzler for minor league pitcher Tim Alderson. Neither player saw Major League time after the deal, and only Canzler had big league time prior. I mentioned it here more for the fact that Alderson was the one-time high upside prospect in the Freddy Sanchez deal, who lost velocity early in his pro career and never regained it.
Prior to the 2015 season, the Pirates traded outfielder Travis Snider for minor league pitchers Stephen Tarpley and Steven Brault. Tarpley was the higher upside pitcher, but he got sidetracked by injuries, while everyone here knows about Brault. Tarpley’s value to the Pirates was a trade piece for Ivan Nova. Snider played poorly in Baltimore and was released, then signed with the Pirates to finish out the 2015 season, so this deal worked out well.
In late August of 2016, the Pirates acquired pitcher Zach Phillips for pitcher Kyle Lobstein. Phillips pitched well over eight appearances, in what ended up being his final big league time (though he was active in pro ball still in 2019). Lobstein had some brief big league time before the deal, but he has been in the minors since.
The most recent deal between the two clubs was last year when the Pirates acquired pitcher Yefry Ramirez for minor league infielder Patrick Dorrian. We will have to wait to see about this deal. Dorrian could give the Orioles and edge or just make it a wash, as Ramirez is no longer around and he pitched poorly in his 14 innings with the Pirates.
Here are the previous Trade History articles:
New York Mets
John started working at Pirates Prospects in 2009, but his connection to the Pittsburgh Pirates started exactly 100 years earlier when Dots Miller debuted for the 1909 World Series champions. John was born in Kearny, NJ, two blocks from the house where Dots Miller grew up. From that hometown hero connection came a love of Pirates history, as well as the sport of baseball.
When he didn't make it as a lefty pitcher with an 80+ MPH fastball and a slider that needed work, John turned to covering the game, eventually focusing in on the prospects side, where his interest was pushed by the big league team being below .500 for so long. John has covered the minors in some form since the 2002 season, and leads the draft and international coverage on Pirates Prospects. He writes daily on Pittsburgh Baseball History, when he's not covering the entire system daily throughout the entire year on Pirates Prospects.