Revisiting O's top 5 Winter Meetings deals

December 7th, 2020

Every December, the baseball world convenes for a week of industry-wide newsmaking intrigue known as the Winter Meetings, a tradition that dates back to the late 1800s. While they will occur virtually this year for the first time due to the coronavirus pandemic, that shouldn’t stop teams from maneuvering toward 2021: Needs will be addressed and moves will be made, so buckle up.

The Orioles have made their share of splashes over the years, including one of the most memorable of all time. That famous deal tops our list of the top Winter Meetings transactions in O’s history:

1) Dec. 9, 1965: goes to Baltimore
BAL acquired: OF Robinson
CIN acquired: RHP Milt Pappas, RHP Jack Baldschun, OF Dick Simpson

Robinson’s arrival didn’t just alter the course of the Orioles franchise, it also shaped baseball history. And it was legendary executive Lee MacPhail’s parting gift to Baltimore: Before leaving the O's after the 1965 season, MacPhail used those Winter Meetings to negotiate the deal with the Reds that swapped Robinson for Baldschun, Pappas and Simpson.

MacPhail needed incoming general manager Harry Dalton’s approval for the deal, and once he signed off, what turned out to be a heist for the ages was complete. Motivated by Reds owner Bill DeWitt’s comment that Robinson was “an old 30” prior to the trade, Robinson responded with the best stretch of his Hall of Fame career: He won the 1966 Triple Crown and the American League Most Valuable Player Award, as well as two World Series rings across six years in Baltimore. He was eventually enshrined in Cooperstown as an Oriole.

2) Nov. 26, 1962: Bring on

Blair has the eighth-highest WAR (39.7), per Baseball Reference, of any Oriole. He’s one of the franchise’s top two center fielders, an elite defender who won eight Gold Glove Awards and four World Series rings (two with Baltimore). Not bad for a Rule 5 pick.

These days, the Orioles are associated with the Rule 5 Draft because they’ve made at least one selection every year since 2006. Their all-time best Rule 5 pick is inarguably Blair, whom the expansion Mets left unprotected as an 18-year-old after their inaugural season in 1962. Blair debuted in Baltimore in ’64, and he soon blossomed into a centerpiece of the O’s dynasty that won four AL pennants between '66-71.

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3) Dec. 4, 1968: Calling “Crazy Horse”
BAL acquired: LHP , SS Enzo Hernandez, INF Tom Johnson
HOU acquired: OF Curt Blefary, INF John Mason

The Orioles were buying low when they sent former AL Rookie of the Year Award winner Blefary to the Astros as part of a five-player deal for Cuellar one winter before embarking on the most successful stretch in club history. Cuellar was a big reason why, and acquiring “Crazy Horse” at the 1968 Winter Meetings is remembered as one of Dalton’s greatest moves.

A 1967 All-Star coming off a down year, Cuellar quickly regained his form. He went 23-11 with a 2.38 ERA in his first season as an Oriole, sharing AL Cy Young Award honors with Detroit's Denny McLain. Cuellar won at least 20 games in each of the next two seasons, going 143-88 with a 3.18 ERA across eight seasons in Baltimore as part of the famously dominant Oriole rotations of that era. Blefary played one year in Houston, then bounced around and was out of baseball soon afterward. Cuellar ranks fourth on the O’s all-time wins list (143) and second in complete games (133).

4) Dec. 18, 2003: Show Miggy the money

Everyone expected the Orioles to be active at the 2003 Winter Meetings after they made clear they planned to add about $40 million to their payroll with an eye toward competing in the AL East. They made a splash by reeling in , signing the '02 AL MVP to a six-year, $72 million deal. It was both the longest and largest free-agent contract in franchise history at the time.

What followed was a productive but tumultuous tenure in Baltimore. Tejada set a single-season franchise record with 150 RBIs in 2004, made three All-Star appearances and hit .311 with 102 homers and an .862 OPS from ’04-07 with the O’s. But he was also accused of using performance-enhancing drugs and demanded repeatedly to be traded -- which he ultimately was, to the Astros, at the ’07 Winter Meetings.

5) Dec. 4, 1974: comes to town
BAL acquired: OF Singleton, RHP Mike Torrez
MON acquired: LHP Dave McNally, RF Rich Coggins, RHP Bill Kirkpatrick

GM Frank Cashen needed to replace Boog Powell after the 1974 season, and he used the Winter Meetings that year to swing a five-player deal with the Expos that netted Singleton for rotation stalwart McNally and two others. McNally was in the twilight of his career at the time; Singleton was entering his prime and underrated, given how much of his value was wrapped up in plate discipline and on-base ability.

Those qualities became a fixture in the Orioles' lineup for a full decade, over which Singleton batted .284/.388/.445 with 182 home runs and produced 30 WAR, per Baseball Reference. He was a cog on postseason teams of the late 1970s and early ‘80s, making three All-Star appearances and finishing in the top 10 in AL MVP voting three times with the O's.

Honorable mention -- Dec. 9, 2010: Hey, J.J.
BAL acquired: SS , INF Brendan Harris
MIN acquired: RHP Jim Hoey, RHP Brett Jacobson

What registered as an under-the-radar deal at the time paid dividends in the decade to come. The O’s were still a few years away from contention when GM Andy MacPhail bought low on former All-Star shortstop Hardy, acquiring him and utility man Harris from the Twins for Minor Leaguers Hoey and Jacobson at the 2010 Winter Meetings.

Hardy hit a career-high 30 homers the following season, then won consecutive Gold Glove Awards from 2012-14 while the Orioles re-emerged as postseason contenders. Among shortstops in O’s history, Hardy ranks second all-time in homers (107) and third in RBIs (385) and games played (887).