On the anniversary of their worst trade, here are the O's five most notable deals - BaltimoreBaseball.com

Dan Connolly

On the anniversary of their worst trade, here are the O’s five most notable deals

In preparing for a speech Monday night about the Orioles and Major League Baseball, I decided to flip through the book I wrote in 2015.

I ended up on the chapter chronicling the Orioles’ most notable trades, and realized that today is an anniversary of one of them.

It has been 26 years since Jan. 10, 1991 – the date of the most infamous deal in club history. Team executive Roland Hemond knew he was giving up a lot when he shipped a trio of promising young players – pitchers Curt Schilling and Pete Harnisch and outfielder Steve Finley – to the Houston Astros. But Hemond believed first baseman Glenn Davis was the missing ingredient in the club’s pursuit of a pennant.

The Orioles lacked prodigious power and the right-handed-hitting Davis had bashed 166 homers in parts of seven seasons while playing half of his games in the spacious Astrodome. Well, we all know how that one turned out. Davis hit just 24 homers in parts of three, injury-riddled seasons for the Orioles. And that trio of young players made a combined nine All-Star teams.

When I ranked the Top 10 most notable trades in O’s history – not best, mind you — the Davis deal landed in second. Here is my Top Five – the ranking hasn’t changed since the book was published, though the Mark Trumbo deal last December might have gotten some attention if I had done a Top 20 list.

Here’s my Top 5:

5. February 8, 2008

The Orioles were in a rebuilding phase, so club president Andy MacPhail sent the club’s best starter, lefty Erik Bedard, to the Seattle Mariners for five players. MacPhail, being MacPhail, took his time and got exactly what he wanted: An impressive package of players that included cornerstone outfielder Adam Jones, top starter Chris Tillman, reliever George Sherrill, who became an All Star closer for the Orioles, and two others. Bedard was 15-14 in 46 starts with the Mariners from 2008-2011.

4. December 4, 1968

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Outfielder Curt Blefary was the 1965 AL Rookie of the Year, but by 1968 he had been passed on the Orioles’ depth chart by several players. Wanting another quality arm for the rotation, the Orioles sent Blefary and infielder Enzo Hernandez to Houston for a 31-year-old, left-handed journeyman named Mike Cuellar. That journeyman won a share of the 1969 AL Cy Young Award and posted six straight seasons with 18 wins or more and an ERA under 3.50.

3. June 15, 1976

The Orioles don’t make a whole lot of trades with the New York Yankees – the clubs did agree on a record, 17-player deal in 1954, which I ranked as the ninth most notable in club history – but this one set up the Orioles for their next playoff run. In a 10-player swap, the Orioles acquired catcher Rick Dempsey, starter Scott McGregor and reliever Tippy Martinez, as well as pitchers Dave Pagan and Rudy May for pitchers Doyle Alexander, Ken Holtzman, Grant Jackson and Jimmy Freeman and catcher Elrod Hendricks. Dempsey, Martinez and McGregor helped lead the club to two World Series, including the 1983 title. It could have been more lopsided, since lefty Ron Guidry was discussed, but ultimately wasn’t included in the deal.

2. January 10, 1991

The Davis’ trade is the only one in the Top Five that didn’t benefit the Orioles. Boy, did they lose this one. Schilling has a legitimate chance at the Hall of Fame while Finley won five Gold Gloves and made two All-Star games and Harnisch won 111 games in a 14-season career and was an All Star in 1991 for the Astros.

1. December 9, 1965

It is the most lopsided deal in club history. And maybe the most lopsided in baseball history – at least that was the inference when the deal was mentioned in the movie Bull Durham. The Orioles traded Milt Pappas, a quality right-hander at the time, and two others (Jack Baldschun and Dick Simpson) to the Cincinnati Reds for former NL MVP Frank Robinson. Reds club president Bill DeWitt later was quoted as saying Robinson was dealt because he was “not a young 30.” Robinson was, however, an absolute difference-maker. The impact of the trade was immediate. The Orioles won the 1966 World Series and Robinson won the 1966 AL MVP with a Triple Crown season (49 homers, 122 RBIs and .316 batting average), the finest of his Hall-of-Fame career. Pappas was 30-29 with a 4.04 ERA in his tenure with the Reds.

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