Pirates' Top 5 Winter Meetings moves

December 7th, 2020

PITTSBURGH -- The Pirates aren’t typically a team that will “win the offseason.” Even during their successful run of postseason appearances from 2013-15, Pittsburgh built a roster around young players, shrewd signings and opportunistic acquisitions.

So the Pirates are rarely, if ever, the stars of the annual Winter Meetings, the big event of the offseason where major signings and blockbuster trades often go down. But that hasn’t always been true. On more than a handful of occasions, whether people realized it at the time or not, the Bucs were involved in significant transactions.

From a franchise-changing Rule 5 Draft pick to the largest free-agent deal in franchise history, here are the biggest moves the Pirates have made at the Winter Meetings.

1. Selecting in the Rule 5 Draft
Date: Nov. 22, 1954

One caveat: This monumental move didn’t technically take place at the Winter Meetings. According to a United Press story that ran in The Pittsburgh Press on Nov. 22, 1954, the Rule 5 Draft was “generally held in conjunction with the annual Minor League meetings but … being staged separately this year.”

Still, the Rule 5 Draft and the Winter Meetings are always associated together, so we’re including this transaction here. The Pirates sent Branch Rickey Jr. to those separate “Major League draft meetings” on Nov. 22, weeks before the real deal, and paid only $4,000 to select the 20-year-old Clemente from the Dodgers’ Montreal roster.

The story is well known at this point: The Brooklyn Dodgers did what they could to hide Clemente and keep him from being drafted, but the young right fielder from Puerto Rico was simply too talented for scouts to not see his talent. He hit just .257 for Triple-A Montreal in 1954, his first year of professional baseball in the United States, but he was available in that year’s Rule 5 Draft because he had signed with the Dodgers for $10,000.

The first sentence of the next day’s Associated Press story read, “Baseball men were still talking today over the way Branch Rickey ‘pulled one over’ on his former partner Walter O’Malley by grabbing off one of Brooklyn’s prize farmhands for the paltry sum of $4,000 at the annual Major League draft meetings.”

Even then, Clemente was defined in reports as a “great prospect” and “sure-fire star.” Described as “jubilant” after making the pick, Rickey Jr. said this of Clemente to the AP: “He can run and throw. I think he will hit too.” A few weeks later, at the outset of the Winter Meetings, Pirates general manager Branch Rickey told The Pittsburgh Press: “We may have a sleeper in Roberto Clemente.”

Oh, did they ever. Clemente recorded 3,000 hits while winning two World Series during his Hall of Fame career with the Pirates, and he is remembered as the game’s greatest humanitarian -- an amazing player and an even more incredible man.

2. Acquiring in a four-team, 11-player trade
Date: Dec. 8, 1977

The highlight of the 1977 Winter Meetings was a massive swap involving the Pirates, Rangers, Mets and Braves. According to the AP report out of Honolulu, where the Meetings were held, the four-team, 11-player trade “shocked baseball’s Winter Meetings in a turbulent session of trading and executive decisions.”

In the end, the Pirates dealt away All-Star Al Oliver and Minor League infielder Nelson Norman. Oliver went on to make four more All-Star teams after leaving Pittsburgh, but in return, the Pirates received Blyleven and corner outfielder/first baseman John Milner, two key players on the Bucs’ 1979 World Series championship team.

Blyleven was already established as a front-line pitcher and enjoyed three solid years with Pittsburgh. The Pirates won all three of his excellent outings in the ’79 postseason, and he was the winning pitcher (as a reliever) in Game 5 of the World Series to keep the Bucs alive after they fell in a 3-1 hole. Milner went on to spend parts of five seasons with the Pirates, none better than the ’79 campaign in which he hit .276 with 16 homers in 128 games.

The full deal also involved Willie Montanez, Tom Grieve and a player to be named later (Ken Henderson) going to the Mets; Tommy Boggs, Adrian Devine and Eddie Miller to the Braves; and Jon Matlack joining Oliver and Norman as the Rangers’ return. According to the AP report that day, “It was believed to be the biggest Winter Meetings deal” since the Yankees and Orioles pulled off a 17-player trade in 1954.

3. Trading for Matty Alou
Date: Dec. 1, 1965

The Pirates believed that Alou was a better hitter than he’d shown while playing his home games at San Francisco’s Candlestick Park, and they were proven right after acquiring him at the 1965 Winter Meetings near Miami.

To get Alou, the Pirates sent lefty Joe Gibbon -- the 1960 World Series champion who’d wind up with the Bucs again only four years after this deal -- and catcher Ozzie Virgil. Alou won a batting title by hitting .342 during his first season with the Pirates, and he wound up with a .327/.360/.398 slash line, almost 20 stolen bases per season and two All-Star nods during his five years with Pittsburgh.

4. Landing former MVP
Date: Dec. 1, 1966

The 1966 Winter Meetings were held in Columbus, Ohio, only a few hours from Pittsburgh, and the Pirates brought home a star. The Pirates were happy to take him, sending third baseman Bob Bailey and infielder Gene “Stick” Michael to Los Angeles to get Wills.

Wills was a seven-time All-Star and the NL MVP in 1962, when he stole 104 bases while batting .299, but he had fallen out of favor with Dodgers management. He didn’t turn out to be a great player for the Pirates, hitting .290 with 81 steals over two seasons while mostly playing third base, but the move was still big news at the Winter Meetings given Wills’ fame.

5. Richie Zisk for
Date: Dec. 10, 1976

The Pirates traded Zisk, a slugger in his prime who’d just hit 21 homers with 89 RBIs in 1976, to the White Sox along with pitcher Silvio Martínez. In return, they received two relief pitchers who were about to become free agents: lefty Terry Forster and the right-handed Goose Gossage.

Forster went 6-4 with a 4.43 ERA in 87 1/3 innings over 33 games and went on to pitch for 16 years in the Majors. Meanwhile, Zisk made All-Star teams each of the next two years and might have peaked with a 30-homer, 101-RBI season for Chicago in ’77.

Gossage was in the early stages of his Hall of Fame career, and the 1977 season he put together in Pittsburgh was one of his best. Gossage went on to record a 1.62 ERA, a 0.96 WHIP, 11 wins and 26 saves in 133 innings over 72 appearances while making the All-Star team.

Honorable mentions

Dock for Doc
Date: Dec. 11, 1975

Not all “big” moves are good moves, as proven by this trade made at the 1975 Winter Meetings in Hollywood, Fla. The Pirates gave up starter , lefty Ken Brett and second baseman and received only right-hander Doc Medich in return from the Yankees.

At the time, Pirates general manager Joe Brown told the Pittsburgh Post-Gazette that he “never thought we’d be able to obtain a pitcher of Medich’s caliber. We consider him one of the finest young pitchers in baseball.” But the finest young player in the deal wound up going to New York.

Medich, a University of Pittsburgh medical school student at the time of the trade, went 8-11 with a 3.51 ERA in his only season with the Pirates. Ellis' best years were in Pittsburgh, but he was an effective starter for the Yankees in 1976. And Randolph, blocked at second base in Pittsburgh by Rennie Stennett, put together an excellent career as a six-time All-Star and member of the Yankees' back-to-back World Series championship teams in 1977-78.

The biggest free-agent deal in franchise history
Date: Dec. 9, 2014

The Pirates officially re-signed on Dec. 12, 2014, a few days after the Winter Meetings in San Diego, but news broke during the Meetings that Pittsburgh had agreed to bring back the lefty starter -- fresh off two career-reviving seasons in black and gold -- on a three-year, $39 million deal.

That may not seem like much, but Liriano’s second deal with the Bucs was -- and still is -- the largest free-agent contract in franchise history. Furthermore, the fact that Liriano returned to Pittsburgh was seemingly proof that the Pirates -- not far removed from a 20-year losing streak -- had established themselves as a legitimately competitive team.

Of course, Liriano delivered uneven results after signing that deal. He was exactly what the Pirates expected in 2015, starting on Opening Day for the second straight year and going on to post a 3.38 ERA in 186 2/3 innings over 31 starts for a 98-win team. But he struggled in 2016 after making his third straight Opening Day start, and he wound up being dealt to Toronto in a controversial trade in which the Bucs included two prospects to help move all of his remaining salary.