Fourteen moves that define Brian Cashman's career

The New York Yankees signed long-term general manager Brian Cashman to a three-year extension on Friday, continuing the tenure he started in 1998. In 17 seasons, Cashman's clubs have won four World Series titles, and made the playoffs 14 times. Cashman has also personally authorized the signing of something like $40 billion worth of contracts, so, free agents in your mid- to late- thirties, stand and cheer, "Three more years! Three more years! Three more years!"

In honor of New York's fourteen playoff teams under Cashman, here are fourteen of his best and worst moves.

The good

Trading Ricky Ledee for David Justice. The 34 year-old Justice came over from the Indians, hit 20 home runs in 78 games (for a career-high 41 on the year), won the ALCS MVP, and helped the Yanks win the 2000 World Series. All this for Ricky Ledee.

Signing Mike Mussina. Cashman signed Mussina away from the AL East rival Orioles in the 2000 offseason, and pitched for the Yankees (without significant injury!) for eight seasons, accruing a 3.50 FIP during that time.

Trading Alfonso Soriano for Alex Rodriguez. Alex Rodriguez has done a lot of things in his somehow-still-accruing-millions career. Among them: slap at Bronson Arroyo's glove that one time; date Madonna; hit 309 home runs as a Yankee; hit six home runs and drive in 18 in 15 games on the way to New York's 2009 title; have a painting of himself as a centaur commissioned; suspended for steroids. I guess it was worth every penny.

Trading Eduardo Sierra and Ramon Rodriguez for Shawn Chacon. Chacon was great for the Yankees, going 7-3 with a 2.85 ERA down the stretch, and helping New York make the 2005 playoffs.

Trading former first round pick CJ Henry and prospects for Cory Lidle and Bobby Abreu. Abreu hit .330 with seven home runs down the stretch to lead the Yankees to the 2006 playoffs. Abreu then drove in over 100 and stole 20 bags each of the next two years.

Trading Wilson Betemit, Jhonny Nunez and Jeff Marquez for Nick Swisher. This was Cashman's best deal. Swisher hit 105 Yankee bombs in four years, made the 2010 All-Star team, and won a World Series in '09.

Trading Austin Jackson, Ian Kennedy and Phil Coke for Curtis Granderson. Jackson and Kennedy have gone on to become solid players, but Granderson was a stud in the Big Apple. He hit 41 and 43 homers in 2011 and 2012, taking advantage of the absurd right field porch.

Trading two prospects for Kerry Wood. Wood didn't strike out 20 in one game for the Pinstripes. But he did hold down a 0.69 ERA in 26 innings as Mariano Rivera's setup man, as the Yankees marched to the 2010 ALCS.

The bad

Javier Vazquez. Everyone, hug a Yankees fan! (Cashman acquired him not once, but twice!)

Trading Mike Lowell to Florida for Ed Yarnall, Todd Noel, and Mark Johnson. Lowell made the All-Star team four times and won two World Series rings -- once against the Yankees just four years after New York traded him, and once for the hated Red Sox, when Lowell was the World Series MVP.

Signing Carl Pavano. Pavano made 26 starts for the Yankees and had an ERA square at 5.00. For his generous run-gifting, Cashman paid him $38 million.

Trading for Jeff Weaver. Weaver came to Yankee Stadium in the middle of the 2002 season, finishing the season with a respectable 3.52 ERA. But Weaver got shelled in the playoffs, and posted a big, fat 5.99 ERA in 2003. He never pitched for the Yankees again.

Signing Kei Igawa. Ummm. Cashman signed Igawa to a five-year, $20 million deal in 2006. Just, just go look at his Baseball Reference page. I can't type it.

Signing AJ Burnett. AJ signed on to be a Yankee for five years, $82.5 million, which is a lot. AJ only pitched for the Yankees for three of those five years, as Cashman would trade him to the Pirates and continue paying him anyway. Burnett's ERA was over five in his final two Yankee years, and in his three-year run, he lead the league in wild pitches (twice), walks, and hit batsmen. Yay!