By Jim Henneman

In days gone by, baseball's original trading deadline was June 15. It has evolved since into a succession of so-called "deadlines," stretching all the way to Aug. 31, some for straight-up trades, others for the purposes of determining eligibility for postseason play, others pertaining to waivers, etc. In honor of all deadlines past and present, in no chronological order or rank of importance, here's a list of 15 "trading deadline" moves the Orioles have made through the years -- and one they might have liked to make:

1. Why not start with the first deadline-inducing trade in club history? On June 6, 1954, two weeks before the actual deadline, the O's dealt Vic Wertz, who was tired of his blasts dying on the warning track at Memorial Stadium, to the Cleveland Indians in exchange for right-handed pitcher Bob Chakales. Wertz hit only one homer here, but added 14 for the Indians and then hit the most famous drive of his career during the World Series, to the deepest part of the cavernous right-center field in the Polo Grounds -- before Willie Mays caught it, making the signature play of his Hall of Fame career.

2. This is probably one of the least remembered deals in club history, even though it came June 13, 1966, in the midst of the team's first World Series season. With Davey Johnson embedded at second base, the Orioles traded Jerry Adair to the White Sox for knuckle-baller Eddie Fisher. He then shared closing duties during the regular season and spectator status with Stu Miller during the World Series, when the O's used only four pitchers.

3. During the Paul Richards era of the mid-1950s and early '60s, a few favored players got caught going both ways in the revolving door. The first was Gene Woodling, part of the mammoth 18-player trade with the Yankees after the 1954 season. Woodling and Bobby Cox (who refused to report, retired and was replaced by $15,000) went to the Indians for Dave Pope and Wally Westlake June 15, 1955. Woodling came and went again before retiring and eventually becoming a coach under manager Hank Bauer.

4. Dick Williams was another that didn't know whether he was coming or going most of the time. Originally claimed off waivers from the Dodgers June 25, 1956, he was traded to Cleveland for Jim Busby June 13, 1957. Eventually, he was part of six transactions that involved the Orioles.

5. Then there was Dave Philley, who had been claimed on waivers from the Indians July 2, 1955. A switch-hitter, who once held the career record for pinch hits, he was traded along with pitcher Jim Wilson to the White Sox for pitchers Mike Fornieles and Connie Johnson; outfielder Bob Niemann; and George Kell, Brooks Robinson's first major league roommate and third base mentor. Philley eventually returned to the O's in a cash deal Sept. 1, 1960; was released Oct. 13, 1960; re-signed Jan. 31, 1961; and released again Oct. 9, 1961 -- before re-joining Richards with the Houston Colt .45s.

6. The granddaddy of all June trades for the Orioles took place June 15, 1976, when they sent Ken Holtzman (obtained with Reggie Jackson as part of the preseason deal that sent Don Baylor and Mike Torrez to Oakland), Doyle Alexander, Grant Jackson, Elrod Hendricks and minor leaguer Jimmy Freeman to the Yankees for Rick Dempsey; Tippy Martinez; Rudy May; Dave Pagan; and Scott McGregor, who was then still in the minor leagues. It was Hank Peters' second trade as general manager (following the preseason deal with the A's) and set up an offseason deal a year later, which brought Don Stanhouse, Gary Roenicke and Joe Kerrigan from Montreal in exchange for May, who went 29-21 here in a little more than 1.5 years.

7. This is a twofer -- Willie Tasby went to Boston for Gene Stephens in a straight-up swap of outfielders June 9, 1960. Less than a year later, Stephens went to Kansas City in exchange for Marv Throneberry, whose claim to fame was being an original Met and a punch line on Miller Lite commercials.

8. How could we leave out a deal that included both Woodling and Williams? That took place not at a deadline, but during spring training, just before Opening Day -- April 1, 1958. Woodling, Williams and left-handed pitcher Bud Daley went to the Indians for Larry Doby and Don Ferrarese, another left-handed pitcher.

9. The late '80s were a period of turmoil for the Orioles, so it's no surprise there were significant late-season trades, three of them involving four future members of the club's Hall Of Fame, two each coming and going. On Aug. 31, 1987, literally minutes before the deadline for postseason eligibility, Mike Flanagan went to Toronto in exchange for pitchers Oswaldo Perez and Jose Mesa.

10. A year later, July 29, 1988, it was Mike Boddicker going to the Red Sox for Brady Anderson and Curt Schilling, the first half of another twofer. A month later, the Orioles dealt Fred Lynn to the Tigers for three minor leaguers -- pitchers Cesar Mejia and Robinson Garces and catcher Chris Hoiles, who became a fixture behind the plate into the mid-1990s.

George Sherrill

11. George Sherrill, the forgotten player in the Erik Bedard trade that brought Adam Jones to Baltimore, became a closer for the Orioles out of necessity, but was traded to the Dodgers as a setup man July 30, 2009 for third baseman Josh Bell, since dealt to Arizona, and right-handed pitcher Steve Johnson, currently in the rotation at AAA Norfolk.

12. Andy MacPhail earned generally high marks for the trades he made during his four-year tenure with the Orioles, and his last two figure to be future factors for the club. On July 30, 2011, the Orioles traded Koji Uehara to Texas for first baseman Chris Davis and right-handed pitcher Tommy Hunter, both in their mid-20s and with some untapped potential, which could bode well for the future.

13. The Orioles' next deal might have been the steal of the year. Left-hander Michael Gonzalez, mostly ineffective throughout his more-than-1.5-year stay in Baltimore, was sent to the Rangers for a player to be named later, which doesn't generally translate to "a player to be effective later." But early results on this one are beyond positive, as right-handed reliever Pedro Strop has emerged as someone that could be a bullpen fixture for years to come.

14. OK, technically this wasn't a trade, but a deal's a deal, and it's our list, so we can do whatever we want, right? After watching Leo "No Problem" Hernandez fail to tame the hot corner, the Orioles purchased the contract of Todd Cruz from the Seattle Mariners June 30, 1983. After quickly dismissing any thoughts of keeping him at shortstop and moving Cal Ripken to third base, Cruz solidified the O's infield defense (he was involved in 19 double plays as opposed to five before he got here) and moved into the bottom third of the lineup, a charter member of the trio (along with Dempsey and Rich Dauer) Ken Singleton dubbed the "Three Stooges," who nevertheless played a prominent role in the Orioles' most recent World Series championship.

15. This is the trade that wasn't made, but the possibilities were so intriguing. After losing a tense, 2-1 game to open a three-game series at the end of the 1989 regular season, the O's needed to win the last two to force a one-game playoff (in Baltimore). General manager Roland Hemond worked to put a deal in place with Montreal for pending free agent Mark Langston, a dominant left-handed pitcher. His plan was to send Arthur Rhodes, then a promising prospect with a bad knee, to the Expos -- and announce the trade minutes before Game 162, a move that would have stunned the Blue Jays (and probably the O's as well) and left staff ace Bob Milacki available for a possible playoff game. Alas, sometimes the best (or most ingenious) trades are never made.

Issue 174: June 2012