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Esteban Loaiza failed to help the Blue Jays into the 2000 playoffs, posting a 5-7 record and 3.62 earned-run average after a trade from Texas. Shortstop Michael Young, the man Toronto traded, still plays for the Rangers and won a batting title in 2005. ((Aaron Harris/Canadian Press))

For all his failed acquisitions — Luke Prokopec, Jason Arnold, Frank Thomas, Victor Zambrano and Toma Ohka, to name a few — J.P. Ricciardi can't lay claim to what many believe is the worst trade deadline move by a Toronto Blue Jays general manager.

That dubious distinction goes to Gord Ash, who began his tenure with the team in the ticket department in 1978 before advancing to the grounds crew and later the front office, where he served as GM from 1995 to 2001.

Ash, believing his team had a strong chance to end a six-year playoff drought on the heels of back-to-back World Series titles, sent minor league shortstop Michael Young to the Texas Rangers for pitchers Esteban Loaiza and Darwin Cubillan on July 19, 2000.

"How can we consider trading for a guy who will make 12 starts for a guy who will play 12 years," a Blue Jays scout said.

Loaiza ended up making 14 starts down the stretch, posting a 5-7 record and 3.62 earned-run average for a Toronto outfit that finished third in the American League East with a 83-79 record. He was re-signed for two years in which he sported ERAs of 5.02 and 5.71.

Ten years later, Young remains in Texas, in his second season as the Rangers' third baseman. A six-time all-star, Young won the AL batting title in 2005 with a .331 average.

With that, here's a list of 10 notable transactions from years past ahead of Saturday's 4 p.m. ET non-waiver trade deadline:

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Former Cardinals slugger Mark McGwire shattered Roger Maris's record of 61 home runs with 70 in 1998. ((Tom Gannam/Associated Press))

1. Oakland sends Mark McGwire to St. Louis for T.J. Mathews, Eric Ludwick and Blake Stein (July 31, 1997)

McGwire, with his contract set to expire, was sent packing and quickly fell in love with St. Louis. The slugging first baseman homered 24 times in the last two months of 1997 and hit 196 more over the next four seasons, including an epic race in 1998 with Sammy Sosa when he clubbed 70 dingers to Sosa's 66, each eclipsing Roger Maris's long-standing record of 61.

A steroid admission earlier this year would taint McGwire's legacy. Ludwick, Stein and Mathews never made a big impact with the A's.

2. Cleveland deals Cliff Lee and Ben Francisco to Philadelphia for Carlos Carrasco, Jason Donald, Lou Marson and Jason Knapp (July 29, 2009)

Rebuffed in his attempt to acquire then-Blue Jays ace Roy Halladay, Phillies GM Ruben Amaro Jr. settled for Lee, who was 7-9 with a 3.14 ERA in 22 starts for Cleveland on the heels of a 22-win season in 2008 that helped him win the Cy Young Award as the American League's top pitcher.

He pitched a complete game in his Phillies' debut and went 5-0 with a 0.68 ERA in his first five starts. Lee led the Phillies to a 93-69 mark in the regular season on the way to their third straight NL East division title.

In the playoffs, he went 4-0 with a 1.56 ERA in five starts and became the first pitcher since 1903 to pitch a complete game in the World Series, while recording 10 or more strikeouts and not walking a batter.

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Bartolo Colon posted a 3.31 ERA in 117 innings for the Expos in 2002 after being dealt from Cleveland for all-stars Cliff Lee, Brandon Phillips and Grady Sizemore. ((Paul Chiasson/Canadian Press))

3. Montreal trades Cliff Lee, Grady Sizemore, Brandon Phillips and Lee Stevens to Cleveland for Bartolo Colon and Tim Drew (June 28, 2002)

With his team five games behind Arizona for the NL wild-card lead, Expos GM Omar Minaya surprised many with this deal. Colon had success with Montreal, fashioning a 3.31 ERA in 117 innings in that 2002 season, but the Expos missed the playoffs.

He was dealt to the Chicago White Sox in a three-team deal with the New York Yankees before the 2003 campaign, while the Expos moved to Washington following the 2004 campaign.

The Indians received three perennial all-stars, with Sizemore still on board. Phillips is now with the Cincinnati Reds.

4. Chicago Cubs peddle Lou Brock to St. Louis for Ernie Broglio (June 15, 1964)

Brock, who struck out plenty as a Cub, hit .348 with 33 stolen bases the rest of the 1964 season and led the Cardinals to a World Series championship against the New York Yankees.

The NL's best base stealer eight times, Brock also hit over .300 for eight seasons and was inducted into the Hall of Fame in 1985.

Broglio battled a sore arm with Chicago and mustered only seven wins against 19 losses in two-plus seasons.

5. San Diego ships Fred McGriff to Atlanta for Melvin Nieves, Donnie Elliott and Vince Moore (July 18, 1993)

Braves GM John Schulieroz pulled off this shrewd deal, taking advantage of a Padres fire sale and picking up a three-time all-star for three minor leaguers.

McGriff took to his new surroundings, belting 19 home runs in 68 games while driving home 55 runs to help Atlanta edge San Francisco for the NL West title by one game.

The Braves bowed to Philadelphia in the NL Championship Series, but McGriff went on to play in three of the next four all-star games and collect 111 homers and 391 RBIs.

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One-time Braves starter and relief pitcher John Smoltz won 213 games and saved another 154 in 21 big-league seasons. ((Gregory Smith/Associated Press))

6. Detroit deals John Smoltz to Atlanta for Doyle Alexander (Aug. 12, 1987)

The Tigers, seeking a starter in their bid to hold off the Toronto Blue Jays, landed Alexander, a crafty veteran who delivered 9-0 record and 1.53 ERA in 11 starts to propel Detroit to the AL East crown on the final day of the season.

However, Alexander, also known as Dour Doyle, failed to register a win in a five-game loss to Minnesota in the AL Championship Series and sported an ugly 10.00 ERA.

Smoltz, on the other hand, flourished in Atlanta and became one of the best pitchers of his generation, winning 213 games in 21 big-league seasons and saving another 154.

7. Toronto trades David Cone to the New York Yankees for Marty Janzen, Jason Jarvis and Mike Gordon (July 28, 1995)

Like the Loaiza deal, Ash didn't get close to full value for Cone, who ignited the Yankees' playoff push in '95 by amassing a 9-2 record.

Over the next five seasons, the aging right-hander won four World Series rings, was a two-time all-star, led the American League in wins with 20 in 1998, pitched a perfect game and compiled a 55-38 record.

Only Janzen appeared in a game for the Blue Jays.

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Outfielder Manny Ramirez hit .396 with 17 home runs and 53 RBIs for the Dodgers in the 2008 regular season following a midseason trade from Boston. ((Danny Moloshok/Associated Press))

8. Boston Red Sox trade Manny Ramirez to the Los Angeles Dodgers in a three-team deal with Pittsburgh. The Red Sox acquire Jason Bay and Josh Wilson from the Pirates (July 31, 2008)

Ramirez became an instant hit with the Dodgers, averaging .396 with 17 home runs and 53 RBIs, to lead them to a first-round playoff win over the Chicago Cubs before falling to Philadelphia, the eventual World Series champions.

Bay batted .267 with 36 home runs and 119 RBIs for the Red Sox in 2009 before joining the New York Mets as a free agent last December.

9. Seattle sends Derek Lowe and Jason Varitek to Boston for Heathcliff Slocumb (July 31, 1997)

This is one trade the Mariners would love to have back. Slocumb, who was an all-star with Philadelphia in 1995, tossed only 95 innings with Seattle in '97 and '98, going 2-9 with 13 saves and an ERA around 5.00.

Lowe and Varitek were key contributors as Boston ended its World Series drought in 2004. Lowe, who now pitches for Atlanta, has become one of the game's more consistent starters, while Varitek has reached the post-season seven times and won two championships.

10. Cleveland trades Rick Sutcliffe to the Chicago Cubs, along with Ron Hassey and George Frazier, for Mel Hall and Joe Carter (June 13, 1984)

It's considered one of the greatest trade deadline deals in history. After recording a 5.15 ERA in 15 starts with the Indians in '84, Sutcliffe feasted on National League hitters.

In 20 second-half starts, he reeled off 16 victories against one loss with a 2.69 ERA en route to winning the 1984 NL Cy Young Award.

The Cubs followed suit, winning 62 of their final 100 games to secure the first NL East crown in franchise history.

Carter had a career .259 average in 16 seasons, hitting 151 homers and 530 RBIs in five-plus years in Cleveland, but is best known for his Game 6 homer in the bottom of the ninth inning to help Toronto win the 1993 World Series.