After a season in which the #wewontstop O’s came close to getting to the World Series only to get swept in the ALCS Baltimore fans are looking at the off season with a keen eye. Will owner Peter Angelos open his wallet to keep his players that are available for free agency in the nest? Can Dan Duquette come up with some more of his under the radar signings that have heavily contributed to the Orioles return as MLB contenders?

Time will tell & Baltimore fans are hoping for a sustained run of competitive teams in the AL east that can help erase the memories of the 14 years of futility that preceded it.

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With all eyes on the Orioles front office we look back at the Top 5 all time best off-season moves the team has ever made.


5. ROBERTO ALOMAR Signed 1995

(Vince Bucci/AFP/Getty Images)

(Vince Bucci/AFP/Getty Images)

Already a premiere second baseman with the HOF in his sights when the Orioles signed him as a marquee free agent in 1996. Roberto did not make Peter Angelos regret opening his wallet when the team signed him to a 3 year, $17 Million contract.

Alomar’s 1996 campaign was one of the best ever for a 2nd baseman as he hit .328, drove in 94 runs and hit 43 doubles & 22 home-runs on the way to winning the Gold Glove & Silver Slugger awards in addition to an All Star spot. He was an All Star all 3 of his seasons with the O’s & was the 1998 All Star MVP in addition to another Gold Glove in 1998.


 Credit: Doug Pensinger  /Allsport

Credit: Doug Pensinger /Allsport

The Orioles got Ken Singleton and Mike Torrez from the Expos in December of 1974 for Dave McNally and Rich Coggins. Singleton was a three-time All-Star for the Orioles and made the team’s HOF. Torrez won 20 games in 1975. McNally retired during the year and Coggins was out of baseball by the end of the ’70’s.

3. MIKE CUELLER Trade 1968

Credit: Getty Images

Credit: Getty Images

In December of 1968, the Orioles got Mike Cuellar from the Astros for Curt Blefary. Cuellar won 20 games or more for Baltimore four times and was co-Cy Young in 1969 & pitched the clinching game in the Orioles 1970 World Series Championship run. Blefary played one year for the Astros before bouncing around the league as mostly a part time player.


(Photo by Patrick Smith/Getty Images)

(Photo by Patrick Smith/Getty Images)

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When the Orioles traded their #1 starter to the Seattle Mariners in 2008 many Orioles fans were upset. After all, Bedard had 2 years left on his contract & had finally (it seemed) come into his own as an ACE with a 15 win season followed by a 13 win season on a team that wasn’t getting very many wins.

What did the Mariners get? A guy who couldn’t stay healthy & won 6 games in his best season for them before being given up on & bouncing around the league without ever being effective for any length of time again.

What did the Orioles get? 5 prospects including our current perennial All Star, Gold Glove winning Center Fielder Adam Jones. The Orioles also got Chris Tillman who has matured into a front of the line starter in the last 2 years with 16 & 13 wins.  The O’s also got George Sherrill who was a very effective closer for almost 3 years with the team before being traded to the LA Dodgers.

1. FRANK ROBINSON Trade 1965

(Photo by Mitchell Layton/Getty Images)

(Photo by Mitchell Layton/Getty Images)

The Orioles sent the Cincinnati Reds pitchers Milt Pappas, Jack Baldschun and outfielder Dick Simpson for former National League Rookie of the Year Frank Robinson in Dec. ’65. The Reds GM called Robinson “an old 30”.

Frank Robinson went on that year with the O’s to win the Triple crown & AL MVP hitting 49 Home Runs & leading the Orioles to their 1st AL pennant & a World Series sweep of the Dodgers. Robinson played 5 more years for the O’s as the Orioles enjoyed a run successful years & another World Series in 1970 (over the Reds) becoming a hall of famer & one of Baltimore’s most beloved Orioles.


Honorable Mentions:

Steve Stone: A journeyman pitcher the O’s signed in 1978 for 700 K, he turned in a 25 win season in 1980.

Nelson Cruz: Signed to a 1 year deal in 2014. Lead all of MLB with 40 Home-runs on the year & earned an All Star nod

Randy Meyers:  Signed to a 2 year deal in 1995. Had 45 saves in 1997 was All Star & came in 4th in both Cy Young & MVP voting .


Chris Spiridigliozzi
Web Administrator for CBS Radio Baltimore – Ravens, Orioles & snark enthusiast.

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