The Best And Worst Offseason Moves Of The Orioles’ History

By Paul Folkemer

As general manager Dan Duquette and the Orioles navigate the hot stove season, many fans are tracking their every move, awaiting the Birds’ next transaction, which could propel them forward — or cause them to take a step back. With that in mind, it could be useful to consider the Orioles’ offseason moves of years past. What were the best moves the Birds ever made during the winter months? What were the worst? Let’s take a look.


No. 4: Davey Johnson resigns as Orioles manager (Nov. 5, 1997)
In 1997, the Orioles were one of the best teams in baseball, enjoying 98 wins and a wire-to-wire, first-place finish in the American League East. Little did the Birds know that they were about to crash down to earth — and stay there for 14 miserable years. An event that marked the beginning of the end was Davey Johnson’s resignation after two seasons as O’s manager.

Johnson, who had guided the Birds to the postseason in ’96 and ’97, became embroiled in a personality conflict with owner Peter Angelos. The feud reached a boiling point when Angelos objected to a midseason incident in which Johnson had ordered second baseman Roberto Alomar to pay a fine to a charity that involved Johnson’s wife. The acrimony between the two became untenable, and Johnson submitted his resignation Nov. 5 — ironically, the same day he was named AL Manager of the Year. 

With Johnson gone, the Birds collapsed to a 79-83 record in 1998 with largely the same roster. There’s no guarantee the O’s would’ve remained a winning team with Johnson at the helm, but running off a successful manager after two years certainly didn’t do the Orioles any favors.

No. 3: Orioles hire Syd Thrift as general manager (Dec. 22, 1999)
In the midst of the Orioles’ 14-year losing spell, the Birds made the fateful decision to promote Syd Thrift, their farm director, into the general manager’s chair. Although Thrift was a longtime baseball man who had enjoyed previous success as an executive, his tenure in Baltimore was a disaster.

Thrift, who was 70 years old when he took the reins, seemed a step behind at every turn. Perhaps his most noticeable misfire occurred in 2000, when Thrift gutted the roster and traded away six of the team’s veterans in a fire sale. Thrift got fleeced in nearly every deal. 

Of the six young pitchers he acquired, four of them didn’t make it to the majors, one (Luis Rivera) was damaged goods who made one appearance for the Birds before injuries ended his career and the last (Leslie Brea) was actually five years older than he had said he was. One of the few positives from the haul was Melvin Mora, who was acquired for Mike Bordick and emerged as a useful player.

By the time Thrift left the Orioles in 2002, the team was five seasons into its losing streak with little talent at the major league level and a barren farm system, worse off than it had been when he took over.

No. 2: Mike Mussina leaves the Orioles for the Yankees (Nov. 30, 2000)
Are you noticing a theme with these regrettable offseason moves? Many of them occurred during the late ’90s and early 2000s, a dismal stretch during which seemingly everything the O’s touched turned to dust, (and I didn’t even include the Albert Belle signing in 1998, in which Angelos inked Belle without the knowledge of then-general manager Frank Wren). But amid the frequent changes in the front office and coaching staffs and shuffling of the roster, the most costly player departure may have been Mike Mussina’s.

Mussina was a true success story for the Orioles, a pitcher drafted and developed by the team who emerged into an elite, bona fide ace. Mussina won 147 games and posted a 3.53 ERA during 10 seasons for the Orioles, making his mark as one of the best starting pitchers in franchise history.

But Mussina — seemingly unhappy with the direction in which the Orioles were headed — bolted Baltimore during free agency to sign a six-year, $88.5 million deal with the divisional rival Yankees. To this day, many O’s fans haven’t forgiven Mussina for grabbing the money to sign with New York, while others blame Angelos and the Orioles for not making a bigger push to sign him. Whatever the case, Mussina’s departure struck another devastating blow for an O’s team that has struggled to find an ace throughout the 13 years since.

No. 1: Orioles trade for Glenn Davis (Jan. 10, 1991)
Nearly a decade before those other shenanigans, the Orioles were on the wrong end of one of the most lopsided trades in baseball history, acquiring slugging first baseman Glenn Davis from the Astros in exchange for three young players. The O’s thought Davis — who’d hit 20 or more homers for six years in a row — would provide an impact bat in the middle of their lineup and vault the team into contention.

Instead, Davis torpedoed his Orioles career with an almost laughably sad mixture of ineffectiveness, injury and bad luck. He broke his jaw in a bar fight. He got hit in the head by a foul ball while sitting in the dugout. He suffered a mysterious neck injury. And his three-year O’s career consisted of 24 total home runs before he was practically booed out of town.

And the three players the O’s gave up? One was Curt Schilling, who went on to win 216 major league games, play for six All-Star teams and make a strong case for Hall of Fame enshrinement. Another was outfielder Steve Finley, who hit 304 home runs during a 19-year career. The third, Pete Harnisch, spent 14 solid years in the bigs.

Considering how much the O’s gave up and how little they received, it’s hard to imagine how a trade could possibly turn out worse. It’s not surprising that many fans consider the Davis trade the biggest blunder in Orioles history.


No. 4: Orioles and Yankees make 17-player trade (Nov. 17, 1954)
After the Orioles completed their first season in Baltimore, they pulled off a gigantic mega-trade, giving up seven players and acquiring 10, which remains the biggest trade in MLB history in terms of the number of players involved.

The players acquired as part of the initial swap included Gus Triandos and Gene Woodling, both members of the  Orioles Hall of Fame, and the effects of the trade remained in the organization for more than 30 years. Willy Miranda, also acquired as part of the swap, was later dealt for Jim Gentile, another member of the Orioles Hall of Fame. 

There’s more. Gentile was re-traded for Norm Siebern, who was swapped for Dick Simpson, who was one of the three players sent to Cincinnati as part of the Frank Robinson deal (which we’ll be seeing later on this list). Then Robinson begat Doyle Alexander (among others), who became part of another huge trade with the Yankees, a 10-player swap in 1976, which brought in three more O’s Hall of Famers — Rick Dempsey, Tippy Martinez and Scott McGregor.

Long story short, players continued to be acquired and re-traded until the thread ran out in 1987. The Birds got some incredible mileage — and a laundry list of franchise stars — from that original mega-trade.

No. 3: The Orioles’ 1995 offseason smorgasbord
OK, I’m fudging the rules a bit on this one — I’m combining a full offseason’s worth of transactions into one entry on this list. The Birds made so many significant, franchise-changing moves within a two-month span in 1995 that it’s difficult to separate them.

The changes started at the top, when the Orioles brought in Johnson as their manager Oct. 30, then hired one of the game’s best general managers, Pat Gillick, Nov. 27. With those two experienced winners on board, top-flight players soon followed. The Birds signed closer Randy Myers Dec. 14, and he played a big role in the ’97 wire-to-wire team by going 45-for-46 in save opportunities. On Dec. 20, the O’s inked B.J. Surhoff, who provided great value for the team as a hitter and emotional leader for the next 4.5 seasons.

The day after the Surhoff signing, the O’s landed a free-agent prize by signing Alomar, a Hall of Fame second baseman, to a three-year deal. Alomar racked up three All-Star appearances and two Gold Gloves during his tenure with the Birds and was one of the finest all-around players in baseball.

The Orioles struck gold with nearly every acquisition they made that offseason, from players to coaches to front-office staff. And Angelos was willing to open the checkbook to pay for big-name free agents, something that has become a rarity for him during recent years.

No. 2: Orioles trade Erik Bedard for Adam Jones, Chris Tillman and more (Feb. 8, 2008)
Andy MacPhail’s tenure as general manager in Baltimore wasn’t exactly the stuff of legends — his teams finished in last place in the AL East during all four of his full seasons. But before he left, he laid the groundwork for the Orioles’ 2012 and 2013 success by acquiring key pieces of the team’s nucleus, notably with the successful Erik Bedard trade before the 2008 season.

Bedard, the Birds’ top starting pitcher, was coming off a great 2007 season, and was two years away from free agency. MacPhail snookered Bill Bavasi, who was then the Mariners’ general manager, into giving up five players for Bedard, including Seattle’s top young hitter, Adam Jones, and coveted pitching prospect Chris Tillman. Lefty George Sherrill also came over as part of the trade and enjoyed an All-Star 2008 season as the Orioles’ closer.

Six years later, the trade is still reaping dividends. Jones is now a middle-of-the-order slugger and team leader, while Tillman — after a few stumbles — has developed into one of the Birds’ best starting pitchers. As for Bedard, he has bounced among four teams since the trade without staying healthy and effective for a full season. It’s too early to call this the reverse Davis trade, but the deal looks like a stroke of genius.

No. 1: Orioles acquire Frank Robinson from the Reds (Dec. 9, 1965)
This was an easy pick for No. 1 on the list. It’s pretty safe to say that no single transaction has impacted the Orioles more dramatically than the Frank Robinson trade, a move that vaulted the O’s to their first World Series win and established them as one of the premier franchises in baseball.

The Orioles of the early 1960s were a team on the brink of contention — posting five winning seasons during the first six years of the decade — but were missing that one extra ingredient to push them over the hump. And that’s when Robinson arrived. Robinson was an instant game changer for the Orioles, winning the Triple Crown and AL MVP award during his debut year, when he had 49 home runs and a 1.047 OPS, helping lift the Birds to their first-ever AL pennant and a World Series sweep of the Dodgers.

Robinson’s Orioles playing career lasted six years, which was more than enough time for him to become a Baltimore sports legend. Robinson brought a winning attitude and an elite bat to the Orioles, establishing himself as a fiery leader both on and off the field as well as one of the most productive players in franchise history. That’s not bad for a player the Reds called an old 30. With Robinson at the forefront, the O’s took a stranglehold on the AL, winning 100 or more games three times and making four World Series appearances.


Will the present-day Orioles make a move that ends up on either of these lists? It seems unlikely, unless Duquette acquires a future Hall of Famer, gets swindled into a Davis-esque trade or somehow makes an 18-player swap. But stay tuned.

Issue 192: December 2013


For more from PressBox, read the latest news here.