Top Five Baltimore Orioles Midseason Deals

Throughout their history, the Baltimore Orioles have traditionally never been a hugely active team at midseason.

If one looks at the record book, many of the franchise's most significant deals—Frank Robinson for Milt Pappas; Adam Jones, Chris Tillman and George Sherrill for Erik Bedard; and Steve Finley, Curt Schilling and Pete Harnisch for Glenn Davis—have generally come in the offseason.

However, the Orioles have made some midseason trades that have directly affected the team's fortunes for better or worse. Here now, is a look at my Top Five Orioles midseason deals.

No. 1 - Traded Doyle Alexander, Ken Holtzman, Elrod Hendricks, Jimmy Freeman and Grant Jackson to the New York Yankees for Tippy Martinez, Rick Dempsey, Scott McGregor, Rudy May and Dave Pagan

In one fell swoop, the Orioles laid the foundation for two more World Series appearances, including their last championship in 1983.

While May and Pagan were forgotten in the grand scheme of things, Martinez, McGregor and Dempsey would all be vital components as the Orioles transitioned from the Brooks Robinson Era to the Eddie Murray/Cal Ripken Era. All three were named to the 50 All-Time Favorite Orioles team by the fans.

McGregor won 20 games in 1980 and pitched a shutout in the decisive Game Five of the 1983 World Series against Philadelphia.

Dempsey was a classic "glue guy," who kept his teammates loose with his goofy antics, like turning rain delays into his own personal slip n' slide. But he also came up big when it mattered, hitting a home run and four doubles in the 1983 World Series, earning MVP honors.

Martinez was the Orioles bullpen ace during the 1979 and 1983 World Series runs, as a setup man in the former and as a closer during the latter. One of the franchise's most popular players, Tippy was also on the mound during one of the most famous Orioles games of all time, simply known as "The Tippy Game."

In the top of the 10th inning the Orioles were trailing the Toronto Blue Jays 4-3. Having trailed most of the game, the O's had used their entire bench and had utility infielder Lenn Sakata behind the plate. But Martinez, incredibly picked off three Blue Jays at first base—Barry Bonnell, Dave Collins and Willie Upshall—to retire the side. The Orioles then won the game 7-4 on a game-winning home run by Sakata.

No. 2 - Purchased Contract of Todd Cruz from Seattle Mariners

The late Todd Cruz, who died last September, did not put up gaudy offensive numbers in his stint with the Orioles. Barely hitting .200 for the season, Cruz ended up being a vital piece to the 1983 World Series champions by virtue of his defense.

A shortstop in Seattle, Cruz was moved to third base in Baltimore to replace the ineffective Leo Hernandez and soon solidified the left side of the infield.

As was customary in that season of "Oriole Magic," Cruz was one of the team's unlikely heroes, driving in six runs in his very first game.

Cruz was also known as a quirky character. He was nicknamed "The Watch Man" for the fact that when he showed up in Detroit for his first game with the Orioles, he was wearing three or four watches on his wrist. Cruz, along with Dempsey and Rich Dauer, also made up "The Three Stooges," a name coined by Dempsey for the O's light-hitting 7-8-9 hitters.

No. 3 - 2000 Fire Sale

Heading for a third straight fourth-place finish, then-GM Syd Thrift decided to implode an aging roster and try to rebuild with youth.

Gone were Will Clark, Charles Johnson, Harold Baines, Mike Bordick, and fan-favorite B.J. Surhoff, who was so upset about leaving Baltimore that he cried at his farewell press conference.

And who did the Orioles get in return for all these veterans? How about Hall-Of-Fame snubs like Brook Fordyce, Juan Figueroa, Jose Leon, Lesli Brea, Fernando Lunar and Trenidad Hubbard.

While the decision to break-up an aging, overpaid roster was a wise one, the fact that the Orioles only got one viable major leaguer—Melvin Mora—helped create the current 10-year rebuilding plan the O's are currently on.

No. 4 - Traded Alex Ochoa and Damon Buford to the New York Mets for Bobby Bonilla

He may have been a pain-in-the-neck in the clubhouse but Bobby Bo could swing the stick.

Bonilla was much heralded on his arrival to Baltimore and was a member of the 1996 "Bomb Squad" team that set a then-record for home runs hit by a team. Probably the best Orioles team since the 1983 championship squad, the 1996 Orioles were ousted in the ALCS by the Yankees, partly due to the infamous Jeffrey Maier home run in Game One.

Bonilla signed with Florida before the 1997 season and the Orioles missed his bat, losing to Cleveland in the ALCS while Bonilla won a World Series with the Marlins.

At the time of the trade, Ochoa was being hailed as the next great outfielder by the likes of Peter Gammons, but he ended up having a journeyman career, playing for six teams in nine seasons.

No. 5 - Traded Denny Bautista to Kansas City Royals for Jason Grimsley

The poster child for the Orioles own Steroid Era, Grimsley was a disaster even before he named former teammates when he was busted for using PED's in 2006.

Once Grimsley was busted, other Orioles linked to PEDs in the mid-2000s came fast and furious: David Segui, Brian Roberts, Jay Gibbons, Miguel Tejada, Rafael Palmerio, Sammy Sosa and Larry Bigbie.

Grimsley was not only bad on the mound, he was a kind of symbol for Oriole ineptitude this past decade. A team so bad it couldn't even use steroids right.