Ricky Ledee to Aaron Judge Trade Tree

 

Don't call it a comeback.... but we're back for the first time in what feels like forever with possibly a new set of content for all the Yankees fans reading today. How in the world did Ricky Ledee, I'll give you all a minute to Google the former Yankees left fielder in the dynasty years, lead the Yankees to their captain, Aaron Judge? That's what we are here to discuss with you all today.

The New York Yankees selected outfielder Ricky Ledee in the 16th round of the 1990 MLB Draft. While with the Yankees, Ledee spent parts of the 19998  - 2000 seasons in the Bronx winning two World Series rings with the club. After 62 games with the club in 2000, the Yankees needed an outfield upgrade for the postseason, which led New York to trade Ledee to the Cleveland Indians (Guardians) along with Jake Westbrook and Zach Day for popular star David Justice. 

Justice would stay with the Yankees for the 2000 season, winning a World Series against the New York Mets, as well as the 2001 season, seeing the team fall to the Arizona Diamondbacks in seven games, before being traded to the New York Mets prior to the 2002 season. Justice was traded in a rare cross-town trade with the Mets for third baseman Robin Ventura. 

Ventura was an All Star with the Yankees in 2002, falling short of the ultimate crown of World Series champions, before being flipped to the Los Angeles Dodgers halfway through the 2003 season. On July 31, 2003 the Yankees shipped Ventura off to the Dodgers for RHP Scott Proctor and outfield prospect Bubba Crosby. 

Proctor quickly became one of Joe Torre's favorite and most relied upon reliever during his stint with the Yankees, pitching in a league high 83 games in 2006. Proctor would throw in an identical 83 games during the 2007 season, but only 52 of those innings came with the Yankees, interrupted by another midseason trade back to the Los Angeles Dodgers. For what it's worth, New York didn't do much with Bubba Crosby after the trade aside from using him as our "starting center fielder" in the negotiations with then-Boston Red Sox free agent center fielder Johnny Damon. 

Another July 31 trade for New York saw the addition of infielder Wilson Betemit to bolster their bench, while the Dodgers added back Proctor to strengthen their bullpen. Betemit would spend two seasons in the Bronx, including the final year of the old Yankee Stadium in 2008, before the Yankees, who missed the playoffs for the first time since the 1994 strike-shortened season, went out and aggressively began adding to the team. Betemit was traded to the Chicago White Sox before the 2009 season, along with Jeff Marquez (draftyed and developed by the Yankees) and Jhonny Nunez (who was acquired in a separate trade involving Alberto Gonzalez from the Yankees side) for outfielder Nick Swisher and reliever Kanekoa Texeira. 

The Yankees would go on to win the World Series in 2009, behind Swisher and their flury of new additions, and were back on top of the baseball world. The team could not repeat their successes in 2010, nor in 2011 or 2012 before Swisher left the Yankees via free agency. Swisher would sign with the Cleveland Indians (Guardians) prior to the 2013 season, thus giving New York a compensation pick between the first and second rounds of the 2013 MLB First year Player's Draft. 

With the 32nd pick overall, the New York Yankees selected Aaron James Judge and the rest, as they say, is history. Judge has had a 62 home run season, breaking the American League single-season home run record, along with a 58 home run season in 2024, but the World Series trophy has eluded Judge since breaking through with the team in 2016. 

Imagine a world where the New York Yankees didn't have Aaron Judge playing in their outfield in the Bronx, kind of hard to picture right? Well that would have certainly been a reality had the Yankees not drafted Ledee way back in 1990. A lot of chips had to fall a certain way to lead the team to where they are today and I, for one, am happy with the progression. Judge will presumably spend his entire year with the Yankees as their captain of the squad and we all, as fans, have the likes of Ledee, Ventura, Proctor, Betemit and Swisher, to name a few, to thank for it.

This Day in New York Yankees History 6/29: David Justice the Yankee

On this day in 2000 the New York Yankees tried multiple times to bolster their offense in trades and failed to get Juan Gonzalez and Sammy Sosa before settling for David Justice from the Cleveland Indians for Ricky Ledee and two players to be named later. That trade kind of worked, no?


Also on this day in 1941 Joe DiMaggio and the Yankees played in a double header with the Washington Senators. The wins and losses didn't matter as much as the fact that DiMaggio tied and then broke the American League record for consecutive games with a hit, previously held by George Sisler with 41 straight games with a hit. DiMaggio had a seventh inning single off Walt Masteron to break the tie with Sisler.

This Day in New York Yankees History 6/29: David Justice the Yankee

On this day in 2000 the New York Yankees tried multiple times to bolster their offense in trades and failed to get Juan Gonzalez and Sammy Sosa before settling for David Justice from the Cleveland Indians for Ricky Ledee and two players to be named later. That trade kind of worked, no?


Also on this day in 1941 Joe DiMaggio and the Yankees played in a double header with the Washington Senators. The wins and losses didn't matter as much as the fact that DiMaggio tied and then broke the American League record for consecutive games with a hit, previously held by George Sisler with 41 straight games with a hit. DiMaggio had a seventh inning single off Walt Masteron to break the tie with Sisler.

This Day in New York Yankees History 6/29: David Justice the Yankee

On this day in 2000 the New York Yankees tried multiple times to bolster their offense in trades and failed to get Juan Gonzalez and Sammy Sosa before settling for David Justice from the Cleveland Indians for Ricky Ledee and two players to be named later. That trade kind of worked, no?


Also on this day in 1941 Joe DiMaggio and the Yankees played in a double header with the Washington Senators. The wins and losses didn't matter as much as the fact that DiMaggio tied and then broke the American League record for consecutive games with a hit, previously held by George Sisler with 41 straight games with a hit. DiMaggio had a seventh inning single off Walt Masteron to break the tie with Sisler.

This Day in New York Yankees History 6/29: David Justice a Yankee

On this day in 2000 the New York Yankees tried multiple times to bolster their offense in trades and failed to get Juan Gonzalez and Sammy Sosa before settling for David Justice from the Cleveland Indians for Ricky Ledee and two players to be named later. That trade kind of worked, no?


Also on this day in 1941 Joe DiMaggio and the Yankees played in a double header with the Washington Senators. The wins and losses didn't matter as much as the fact that DiMaggio tied and then broke the American League record for consecutive games with a hit, previously held by George Sisler with 41 straight games with a hit. DiMaggio had a seventh inning single off Walt Masteron to break the tie with Sisler.

The 1990 Draft May Have Been Best Ever For New York

With the 2015 version of the Major League Baseball First Year Players Draft officially in the books prospect humpers (trademark pending) around the country are scrambling for as much information about the newest members of the Yankees family as they can. Hopes are never higher than they are the day after the draft because many fans are left to wonder if so-and-so is the next Derek Jeter or if this guy will be the next Bernie Williams or if the early comparisons to Dellin Betances are warranted or not. While the grade for the Yankees 2015, and probably their 2014 and 2013 drafts as well, draft is “I” for incomplete at this point one thing for certain is the 1990 Draft and International signing period may have been the best ever for the New York Yankees.

To start off that 1990 draft the Yankees drafted a lanky left hander named Andy Pettitte, a second basemen Jorge Posada that the team later moved to catcher after concerns with his defense and a pair of outfielders in Ricky Ledee and Shane Spencer. With those four players alone you have to tip your cap to the scouting directors and the team’s personnel but when you also learn that 1990 was the year the team signed a starting pitcher out of Panama named Mariano Rivera you really have to simply bow down and consider yourself not worthy.

Between these five men you have a total of 19 World Series rings, keep in mind that Posada did not get one in 1996, and 14 of the 19 rings alone are between three of the four members of the Core Four. Posada was a five time All Star and five time Silver Slugger Award winner at the catcher position while Pettitte is the Yankees all-time leader in strikeouts with 2,020 with the 1999 ALCS MVP Award hanging up in his shelf at home. Rivera was a 13 time All Star, all-time leader in saves in Major League history and a five Rolaids Relief Awards winner, now named the Mariano Rivera Award, in his illustrious career.

I guess you could say the Yankees did good for themselves in 1990 with the icing on the cake coming in 1992 when the team added that Jeter kid we alluded to earlier in the post. The rest, as they say Yankees family, is history.

Quick Hit: 1990 Draft Signing Period Was The Best

The players that the New York Yankees added in the 1990 MLB First Year Players Draft and International signing period probably made that year the best of all time in the Yankees organization. The Yankees drafted a lanky left hander in Andy Pettitte, a second basemen turned catcher in Jorge Posada, a pair of outfielders in Ricky Ledee and Shane Spencer, and signed a starting pitcher out of Panama named Mariano Rivera.

Between these five men you have a total of 19 World Series rings, Posada did not get one in 1996, and 14 alone are between three of the four members of the Core Four. Posada was a five time All Star and five time Silver Slugger Award winner for catcher. Pettitte is the Yankees all time leader in strikeouts with 2,020 and has the 1999 ALCS MVP Award hanging up in his shelf at home. Rivera was a 13 time All Star, All Time leader in saves in Major League history, and five Rolaids Relief Awards hanging in his house.