Aug. 22, 2007 — Decides to remove interim tag from manager Dave Trembley, MacPhail's first noteworthy personnel move. After the news conference, the Orioles promptly lose the first game of a doubleheader, 30-3, to the Texas Rangers, the most lopsided defeat in club history.
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Feb. 8, 2008 — Probably MacPhail's high-water moment in Baltimore, the long-anticipated trade that sends left-hander Erik Bedard to the Seattle Mariners for five players. The Orioles receive center fielder Adam Jones, pitcher Chris Tillman, closer George Sherrill and two others in a move praised throughout baseball.
Jan. 13, 2009 — Orioles sign Japanese pitcher Koji Uehara to a two-year, $10 million deal, the club's first foray into the Asian market. When hired, MacPhail stressed the importance of making international headway, and oversaw a new academy in the Dominican Republic. But there has been little movement made and few resources dedicated to those markets since.
Jan. 21/Feb. 20, 2009 — In one month, MacPhail announces long-term extensions for two prominent Orioles: right fielder Nick Markakis (six years, $66 million) and second baseman Brian Roberts (four years, $40 million), the most expensive moves of the MacPhail era. The duo played well in 2009, but neither has duplicated that success since, with Roberts appearing in just 98 games the past two seasons because of injury.
July 30, 2009 — In a deadline deal, MacPhail sends Sherrill, an All-Star closer, to the Los Angeles Dodgers for third base prospect Josh Bell and pitcher Steve Johnson. Bell was fairly well-regarded but has not succeeded in the majors, one of several young players acquired by MacPhail who have not lived up to expectations.
Dec. 16, 2009 — While Orioles officials attend the club's annual Christmas party, The Baltimore Sun reports that MacPhail has agreed to terms with two free agents, reliever Michael Gonzalez (two years, $12 million) and infielder Garrett Atkins (one year, $4.5 million). Both players woefully underperformed — Atkins was released in 2010, Gonzalez traded in 2011 — and became the lasting image of MacPhail's tepid and primarily unsuccessful dalliance with free agency. The Gonzalez contract was the highest total value MacPhail doled out as an Orioles executive. He never agreed to a three-year deal, however, meaning he didn't handcuff the organization's future with lengthy free-agent contracts.
Feb. 2010 — The club moves into its new spring training digs in Sarasota, Fla., leaving behind a dilapidated complex in Fort Lauderdale. One of MacPhail's primary goals when he took over the job was to improve the spring training situation, and most specifically, to get the major league and minor league complexes in the same town instead of two-plus-hours apart.
June 4, 2010 — With the Orioles spiraling out of control in another lost season, MacPhail fires Trembley and replaces him, on an interim basis, with Juan Samuel. MacPhail states that Trembley was not to blame for the losing but said a change needed to be made.
July 29, 2010 — Hires Buck Showalter to be the club's 19th manager, a high-profile acquisition that contrasts with MacPhail's understated style, raising the question of how the two will co-exist. That is seemingly answered when the Orioles go 34-23 under Showalter and head into 2011 with increased expectations.
Offseason, 2010-2011 — Building off a rare, late-season high, the Orioles make a flurry of moves in an attempt to fill obvious holes. In separate deals, MacPhail trades four young relievers for infielders Mark Reynolds and J.J. Hardy. He also signs first baseman Derrek Lee, oft-injured starter Justin Duchscherer and nontendered reliever Jeremy Accardo to one-year deals and closer Kevin Gregg for two years. Typical of MacPhail's tenure, the trades were relatively successful and the signings missed the mark.
Feb. 16, 2011 — As spring training begins, the Orioles announce a one-year, $8 million signing of 36-year-old designated hitter Vladimir Guerrero, a likely Hall of Famer. It's the largest annual salary given to a free agent by MacPhail and is much higher than what was believed to be his comfort zone for Guerrero — an indication that owner Peter Angelos instructed MacPhail to make the move to keep the optimism flowing after such a bleak stretch.
March 1, 2011 — Making an appearance at newly renovated Ed Smith Stadium in Sarasota, Angelos tells The Sun that despite MacPhail's being in the final year of his contract, the top executive "isn't going anywhere." The endorsement emphasized the strong working relationship between Angelos and MacPhail, but even then, there was a question as to whether MacPhail would want to stay as president once his contract expired.
Oct. 8, 2011 — Ten days after the Orioles' 14th consecutive losing season ends and a day after a source tells The Sun that MacPhail is stepping down as the club's president of baseball operations, the Orioles confirm MacPhail's departure in a news release.