A look at the Orioles’ most significant trades with each franchise, Part 2: American League

With the Orioles pulling off a flurry of deals before the July 31 non-waiver trade deadline, last week I started reviewing the club’s trade history with every team in the majors. Part 1 covered the National League.

Now, let’s shift to the American League. Which AL teams have the Orioles traded with most often, and what are their best (or worst) deals with each?

As a reminder, I’m only considering trades in which each team gives up at least one player, not deals for cash or international bonus slot money.

Boston Red Sox

Trades: 13

Most recent: June 3, 2015 (Alejandro De Aza for Joe Gunkel)

Notable trade(s): If the Orioles have qualms about trading with AL East rivals, they apparently don’t apply to the Red Sox. The Orioles and Sox have made six player-for-player trades within the last dozen years alone. Most notable was the 2014 deadline deal that brought elite reliever Andrew Miller to Baltimore for Eduardo Rodriguez. Miller was dominant as the Orioles advanced to the ALCS that year, while Rodriguez has been a regular starter for the Sox since 2015.

The Orioles’ best trade with Boston was another end-of-July deal, this one coming in 1988. The Orioles, whose 0-21 start had landed them far out of contention, traded longtime ace Mike Boddicker to Boston for two young players. The first, 21-year-old righty Curt Schilling, went on to have a Hall of Fame-caliber career (but not with the Orioles, who traded him away in a painful deal I’ll discuss later).

The other youngster in the package was a 24-year-old outfielder named Brady Anderson. Thirteen years and 1,759 games later, Anderson wrapped up his prolific Orioles’ career as the club’s all-time leader in stolen bases (307) and ranked top-five in hits (1,614), runs (1,044), doubles (329) and triples (64), posting a historic 50-homer season in 1996 for good measure.

Chicago White Sox

Trades: 19

Most recent: Aug. 30, 2014 (Mark Blackmar and Miguel Chalas for Alejandro De Aza)

Notable trade(s): The Orioles can thank the White Sox for what amounted to a five-year rental of Hall of Fame shortstop Luis Aparicio. Aparicio came up with Chicago and, by the time he was 28, had already racked up a Rookie of the Year award, five All-Star appearances and four Gold Gloves, along with the AL lead in stolen bases all seven years of his career. In 1963, the Orioles made one of their most high-profile trades in their club’s young history, landing Aparicio for four players, including a fellow future Hall of Famer — knuckleballer Hoyt Wilhelm — and another former Rookie of the Year, infielder Ron Hansen.

Aparicio delivered exactly what the Orioles had hoped. The speedster led the league in steals twice more, including a career-best 57 in 1964, and teamed with third baseman Brooks Robinson for a stupendous left side of the infield defensively. Aparicio helped lead the club to its first World Series title in 1966.

The Orioles traded Aparicio back to the White Sox after the 1967 season. That deal reaped dividends, too, as Baltimore acquired Orioles Hall of Famer Don Buford, a 1971 All-Star.

Cleveland Indians

Trades: 20

Most recent: April 7, 2014 (Torsten Boss for Preston Guilmet)

Notable trade(s): The Orioles have traded with the Indians more than with any other MLB club, making 20 player-for-player deals with Cleveland since 1954.

Surprised? I was. For all the trades between these two clubs, very few have stood out as franchise-altering deals. In the early seasons of the Orioles’ existence, they spent a lot of time just swapping players back and forth with Cleveland. Gene Woodling, Dick Williams, Dave Pope and Hoot Evers each were traded from the Orioles to the Indians and then back to the Orioles, or vice versa.

Perhaps the most significant deal between the two came in 1996. The Orioles, looking for a bat to fuel their wild card run, acquired one they knew extremely well: Orioles legend Eddie Murray. Eight years after Murray’s outstanding initial stint in Baltimore had ended on bad terms, the parties let bygones be bygones and reunited in a July 21 swap for lefty Kent Mercker.

The trade allowed the 40-year-old Murray — who was sitting on 491 career homers when the Orioles reacquired him — to hit his 500th homer in a Baltimore uniform. He accomplished the feat Sept. 6. His bat helped fuel the Orioles down the stretch, and he went 10-for-30 in the postseason. Murray’s successful final stint with the Orioles helped ease some of the sting of his ugly previous departure.

This was the second time these teams exchanged a star first baseman. In the other case, the slugger went the opposite way, with the Orioles trading Boog Powell to the Indians in 1975 for a middling return.

Detroit Tigers

Trades: 14

Most recent: March 24, 2014 (Alex Gonzalez for Steve Lombardozzi)

Notable trade(s): Whenever the Orioles make a notable deal with the Tigers, it always seems to involve a catcher. Such was the case with one of the best-hitting catchers in Baltimore history, Orioles Hall of Famer Gus Triandos, who was a three-time All-Star during his eight-year stint with the club from 1955-1962. The slugger was coming off an injury-plagued, unproductive 1962 season when the Orioles traded him to the Tigers for fellow catcher Dick Brown.

In 1988, the Orioles pulled off a great deal at the August 31 waiver-trade deadline, sending outfielder Fred Lynn to the Tigers for catching prospect Chris Hoiles. Hoiles spent the next decade in Baltimore, bashing 151 homers (142 as a catcher), the most in Orioles’ history for a backstop. He was inducted into the Orioles Hall of Fame in 2006.

With Hoiles’ emergence, the Orioles needed to find a new home for their previous catcher, 1989 All-Star Mickey Tettleton. In 1991, they traded Tettleton to — you guessed it — the Tigers. He went on to have four strong years in Detroit, while pitcher Jeff Robinson, whom the Orioles acquired for him, had one forgettable season in Baltimore.

Houston Astros (previously Houston Colt .45’s)

Trades: 10

Most recent: July 31, 2013 (Josh Hader and LJ Hoes for Bud Norris)

Notable trade(s): You probably know which trade I’m about to mention. I apologize in advance. If you can’t bear to relive the worst deal in Orioles’ history, feel free to skip to the next team.

If you’re still with me, I appreciate it. Let’s all try to get through this together. It was 1991 when Orioles’ general manager Roland Hemond decided the Orioles needed a powerful bat in the middle of the lineup. He found his target: Astros’ slugger Glenn Davis, who’d hit 20 or more homers in each of his six full seasons in the majors and was NL MVP runner-up in 1986. Hemond ponied up for Davis with three young players: outfielder Steve Finley and pitchers Pete Harnisch and Curt Schilling.

The trade was an unmitigated disaster, one that set the Orioles back for years. Davis fell apart as soon as he got to Baltimore, struggling through three injury-plagued, unproductive seasons and incurring the wrath of unimpressed Orioles’ fans. Davis was batting .177 when his career came to an end in 1993.

It’s bad enough that Davis was a bust. What sealed this swap as one of the worst in baseball history was that all three youngsters the Orioles surrendered went on to have excellent careers. Harnisch pitched for 11 more seasons, finishing his career with an 111-103 record and 3.89 ERA. Finley spent 19 years in the majors, cranking 304 homers and 1,167 RBIs and winning five Gold Gloves. And Schilling was the best of them all, enjoying a 20-year career in which he was a six-time All-Star, three-time 20-game winner, two-time strikeout leader and three-time World Series champion.

I’m going to go out on a limb and say this was a trade the Orioles would like to have back.

Kansas City Royals

Trades: 7

Most recent: Dec. 18, 2013 (Danny Valencia for David Lough)

Notable trade(s): The cupboard is pretty bare in terms of significant trades between the Orioles and Royals. Let’s go with the first trade between these two clubs, the June 1970 deal that brought righty reliever and popular clubhouse cutup Moe Drabowsky — a key part of the Orioles’ 1966 championship team — back to Baltimore after a two-year stint in Kansas City. Drabowsky wasn’t as effective in his second go-round with the Orioles, but managed to pick up his second World Series ring as the club won it all again in 1970.

Los Angeles Angels (prev. Anaheim Angels, California Angels)

Trades: 13

Most recent: May 6, 2017 (Damien Magnifico for Jordan Kipper)

Notable trade(s): In between the careers of Orioles legends Brooks Robinson and Cal Ripken, Doug DeCinces capably manned the hot corner for Baltimore. DeCinces was widely credited with creating “Orioles Magic” in 1979, when he smacked a dramatic, two-out, two-run homer in the bottom of the ninth June 22 to beat the Tigers. But the Orioles Hall of Famer was dealt to the Angels for outfielder “Disco” Dan Ford after the 1981 season. DeCinces went on to have a productive six years for the Angels, while the Orioles — after moving Ripken from third to shortstop early in his career — struggled to find an everyday third baseman during that span.

Minnesota Twins (prev. Washington Senators)

Trades: 11

Most recent: Dec. 9, 2010 (Jim Hoey and Brett Jacobson for J.J. Hardy and Brendan Harris)

Notable trade(s): It’s no wonder the Twins haven’t traded with the Orioles in eight years after getting swindled in the Hardy trade. In 2010, the shortstop had just finished a mediocre season in Minnesota, and the Twins were looking to move him to make room for Japanese free agent Tsuyoshi Nishioka. The Orioles took advantage, acquiring him for two young hurlers.

In Hardy, the Orioles acquired the anchor of their infield for the next seven years. He won three Gold Gloves for the Orioles and had great pop for a shortstop, at least for the first half of his Baltimore career. Meanwhile, the Twins gained nothing from the trade. Hoey made just 26 appearances for Minnesota and Jacobson never got to the majors, while Nishioka was a bust.

New York Yankees

Trades: 13

Most recent: July 24, 2018 (Zach Britton for Cody Carroll, Josh Rogers and Dillon Tate)

Notable trade(s): When the Orioles dealt Zach Britton to the Yankees last month, much was made about how the two teams have rarely traded in recent years; the Britton deal was just the second in the last 25 years. In the decades before that, though, the two teams collaborated on two of the biggest trades in Orioles’ history — one by size, and one by importance.

On Nov. 17, 1954, the Orioles and Yankees set a major league record that still stands today by pulling off an incredible 17-player deal. (I’d love to see a 17-player trade today, if for no other reason than to see Twitter literally explode.)

Ten players went to the Orioles and seven to the Yankees. Among the cavalcade of players joining Baltimore were Orioles Hall of Famers Gene Woodling (for the first of his two stints) and Gus Triandos. Going the other way were pitchers Don Larsen and Bob Turley, both of whom became quality starters for the Yankees, with Larsen pitching a perfect game in the 1956 World Series.

In 1976, the two teams connected on another enormous trade, a 10-player deal June 15 that sent five players each way. This one left quite an impact in Baltimore. Three of the five players the Orioles acquired have since been inducted into the club’s Hall of Fame. They included Scott McGregor, who spent his entire 13-year big league career in Baltimore, winning 138 games; lefty Tippy Martinez, a stellar reliever for 11 seasons who ranks fourth on the Orioles’ all-time saves list; and Rick Dempsey, the 1983 World Series MVP, who caught for a decade in Baltimore and is still a regular presence at Camden Yards.

The Yankees didn’t fare nearly as well in their side of the trade. None of the five players they acquired spent more than three seasons in pinstripes.

Oakland Athletics (prev. Kansas City Athletics, Philadelphia Athletics)

Trades: 19

Most recent: Nov. 22, 2017 (Jake Bray for Jaycob Brugman)

Notable trade(s): The Orioles’ very first trade partner after moving to Baltimore in 1954 was the then-Philadelphia Athletics. The Dec. 17, 1953 trade sent former St. Louis Browns’ lefty Bob Cain to the A’s for righty Joe Coleman, who led the inaugural ’54 Orioles with four shutouts. Over the years, several members of the Orioles’ Hall of Fame have changed hands between these two teams, including reliever Dick Hall (traded from the Athletics to the Orioles in 1961), first baseman Jim Gentile (sent the other way in 1963), and designated hitter Harold Baines (dealt from Oakland to Baltimore in 1993).

My personal favorite trade was Ross Wolf for Jake Fox in 2010, probably the only swap in baseball history involving two players whose names are mammals.

The most infamous trade, though, is the one that brought superstar outfielder Reggie Jackson to Baltimore in 1976. The Orioles thought they’d made a championship-caliber acquisition in snaring Jackson, a six-time All-Star and 1973 AL MVP, but the reality played out much differently.

Jackson, upset about the trade and his contract status, didn’t report to the Orioles until his salary dispute was resolved in mid-April, causing him to miss 16 games. His holdout alienated his teammates and Orioles’ fans, especially when he got off to a sluggish start at the plate. Jackson’s bat eventually got hot, but the damage had already been done as the Orioles missed the playoffs. Jackson left for the Yankees in free agency after his lone season in Baltimore.

Seattle Mariners

Trades: 11

Most recent: Jan. 6, 2017 (Yovani Gallardo for Seth Smith)

Notable trade(s): For the first 30 years of the Mariners’ existence, they made only four trades with the Orioles, and at one point went two decades without one. Since 2007, though, the two teams have matched up seven times, usually to the Orioles’ benefit.

Nothing can hold a candle to the Erik Bedard deal in Feb. 2008, one of the greatest trades in Orioles’ history. The lefty, who had two years remaining until free agency, was coming off an outstanding 2007 season (13-5, 3.16 ERA, MLB-best 10.9 strikeouts per nine), and Orioles’ executive vice president Andy MacPhail struck while the iron was hot. He milked five players out of Mariners’ GM Bill Bavasi, headlined by 22-year-old outfielder Adam Jones.

Jones alone made the trade an enormous win for the Orioles. The five-time All-Star, four-time Gold Glover and vocal clubhouse leader is now in his 11th year in the black and orange, where he’s emerged as the face of the franchise. He ranks in the Orioles’ all-time top five in hits, homers and RBIs.

But there’s more. The Orioles also received righty Chris Tillman, then in Single-A, who ultimately made his way up the minor league ladder and emerged as the club’s most reliable starter during their winning 2012-2016 stretch. Tillman’s 10-year run with the Orioles came to an end this season after 210 games pitched.

For good measure, the Bedard trade also yielded closer George Sherrill, who made the 2008 All-Star team. Meanwhile, the injury-plagued Bedard made just 30 starts in his first three seasons in Seattle. He produced a meager 4.1 WAR for the Mariners, while Jones, Tillman and Sherrill combined for 43.1 for Baltimore.

Tampa Bay Rays

Trades: 4

Most recent: July 31, 2017 (Tobias Myers for Tim Beckham)

Notable trade(s): The Orioles’ most recent trade with the Rays hasn’t panned out as well as initially thought. At last year’s trade deadline, the Orioles acquired Beckham, a former No. 1 overall draft pick, from the Rays. The move looked like a stroke of genius during Beckham’s red-hot August, when he batted .394 with a 1.062 OPS and 15 multi-hit games. But Beckham went ice cold in September — a .180 average and .603 OPS — and hasn’t fared much better so far in 2018, offensively or defensively.

Texas Rangers (prev. Washington Senators)

Trades: 17

Most recent: Dec. 1, 2011 (Randy Henry and Greg Miclat for Taylor Teagarden)

Notable trade(s): One of Andy MacPhail’s final trades during his Orioles’ tenure was also one of his biggest masterpieces. On July 30, 2011, he sent reliever Koji Uehara to Texas for two 25-year-olds who had fallen out of favor with the Rangers: Chris Davis and Tommy Hunter.

Though MacPhail didn’t stick around long enough to see it, Davis and Hunter emerged as two important cogs in the Orioles’ run of success that started in 2012. Davis tapped into his prodigious power with 238 homers (and counting) in an Orioles’ uniform, twice leading the majors in long balls, including a franchise-record 53 in 2013. Hunter converted to a relief role and found new life on his fastball, becoming a valuable setup man for the club’s excellent bullpen. Though Davis’ 2016 contract extension has become an albatross for the Orioles, that doesn’t make the initial trade any less superb.

Toronto Blue Jays

Trades: 5

Most recent: Dec. 11, 2000 (Jayson Werth for John Bale)

Notable trade(s): Although the Blue Jays have existed since 1977, they’ve made just five swaps with the Orioles, and none in almost 20 years. The last one involved the Orioles trading Werth, then a 21-year-old catching prospect, who ended up having a productive 15-year career as an outfielder before announcing his retirement this season.

The first trade between these two clubs, in Aug. 1987, was a sad one for Baltimore. The rebuilding Orioles dealt homegrown lefty Mike Flanagan, who’d been in the organization nearly 14 years and won the 1979 AL Cy Young award, to the contending Blue Jays. Flanagan approved the trade but insisted, “I’ll always be an Oriole.” Sure enough, he returned to Baltimore as a free agent in 1991 and spent his final two years with the Orioles, finishing his career ranked third in franchise history in appearances (450).