Best Trades the Yankees Never Made

Here is a look at some of the best trades the Yankees never made.  This was done off the top of my head so if I am missing something please feel free to chime in with a comment.  Here we go, in no particular order:

Joe DiMaggio for Ted Williams – This was pretty close to happening.  In fact, there was a verbal agreement between Yankees GM Larry MacPhail and Red Sox owner Tom Yawkey in 1947.  Both men were drinking and bouncing ideas off of each other.  MacPhail saw Williams and his left handed bat using the short right field post at Yankee Stadium to demolish opposing pitching.  Yawkey saw DiMaggio and his right-handed bat abusing the Green Monster in left field.  When the two men sobered up the next day, Yawkey came to MacPhail and said he just couldn’t trade Williams.  He was worried about the backlash from the Boston fanbase for trading another superstar to the Yankees, even if he was receiving Joe DiMaggio in return.  In hindsight, it is hard to imagine the Yankees without DiMaggio or the Red Sox without Williams.  I think both would have put up better numbers than they did but they were both legends in their cities and this was a deal better off not done.

Frank Thomas for Mariano Rivera and others – Once upon a time Mariano Rivera was a fringe starting pitcher.  That was in 1995, when Rivera filled in as a starter for a bit.  The Yankees coveted Thomas and his awesome bat but were unwilling to deal Rivera.  It turns out the Yankees were right not to do so.  Can you imagine how different the 1990’s would have been had Rivera not been a part?  Can you imagine what Frank Thomas could have done as a Yankee?  Well, we got to see Thomas in a Yankee uniform to whet that appetite in one of the opening scenes in the Tom Selleck movie Mr. Baseball where Thomas is the young rookie that supplants an aging Selleck who reminds me a little of Don Mattingly.  The Yankees ended up trading Russ Davis and Sterling Hitchcock to the Mariners for Tino Martinez, Jim Mecir, and Jeff Nelson.  That trade worked out for the Yankees big-time.

Andy Pettitte for Reggie Taylor, Adam Eaton, and Anthony Schumaker – This was pretty close to happening in 1999.  George Steinbrenner was getting fed up with Pettitte’s slow start and wanted Pettitte traded to send a message to the team.  GM Brian Cashman resisted the urge to deal one of the greatest lefties the Yankees have ever had.  Believe it or not, Reggie Taylor was once a pretty highly regarded prospect but he never got beyond that.  Adam Eaton was another pretty decent prospect but again, he never got beyond that.  Schumaker only made 8 big league appearances.  Phew.  Can you imagine if the Yankees made this deal?  Wow.  The Yankees supposedly would have flipped two of those guys to the Devil Rays (as they were then called) for reliever Roberto Hernandez.  Dodged a huge bullet on this one.

Phil Hughes, Ian Kennedy, and others for Johan Santana – The Twins were dangling their lefty ace.  The Yankees needed pitching.  Talks went back and forth and the Twins asked for Phil Hughes and Ian Kennedy among others.  The Yankees said no.  That was five years ago.  Santana was traded to the Mets for Phil Humber, Carlos Gomez, and Kevin Mulvey.  Humber is now with the White Sox.  Gomez is with the Brewers.  Mulvey is still toiling away in the minors…I think.  The Yankees told the Twins they could have either Hughes or Kennedy.  The Twins wanted both and ended up getting nothing in return for their ace.  The Mets invested big dollars in Santana and got a little return for their money as Santana was an ace before hurting his shoulder.  Now, he is kind of like Carl Pavano for the Mets but if and when he does come back at least he will be better than Pavano.  Ian Kennedy was traded for Curtis Granderson so that worked out, even if Kennedy did win 20 games this past season.

Robinson Cano for anyone – There was a time when Robinson Cano seemed to be mentioned an awful lot in trade rumors.  Here are some of the guys he was in trade talks for:  Freddy Garcia, Jamie Moyer, Alex Rodriguez (Texas chose Joaquin Arias instead of Cano in the Soriano for A-Rod trade), Troy Glaus, Russ Ortiz, and Randy Johnson among others.  The Yankees eventually landed Garcia to a deal last year.  They managed to get A-Rod because Texas chose the younger Arias.  Russ Ortiz was signed as a minor league free agent a couple of years ago but was terrible.  Randy Johnson became a Yankee but Arizona didn’t want Cano.  It would be hard to imagine what the Yankees would be like right now if Cano had been traded away. 

Every winter and every year n June and July we hear different rumors swirl around the Yankees.  It is hard to tell which trades were close to happening and which were just rumors.  We know about the DiMaggio-Williams swap and that the Yankees came close to trading Cano and Mo and Pettitte.  We also know they were close to letting Bernie Williams walk as a free agent and would have instead signed Albert Belle in 1998.  Belle was an offensive force.  However, he happened to have a degenerative hip problem that cost him his career while Bernie is only an All-Time Yankee great.  We all also know how close the Yankees came to signing Greg Maddux, Barry Bonds, Bobby Bonilla, and Vladimir Guerrero in recent years.  Maddux chose Atlanta in 1993 and the Yankees beat him in two World Series in 1996 and 1999.  Bonds went on to the Giants and setting records as well as getting involved in steroids.  Bonilla was good for the Mets for a couple of years but didn’t live up to the contract he signed.  Vlad’s back scared Yankee brass away.  He went on to be a dynamic player and is still playing, albeit at a much lesser level.  Instead of Vlad the Yankees signed Gary Sheffield.  Yankee fans can’t be too upset given what Sheff did as a Yank. 

I just wanted to visit the things that almost altered Yankee history, and ultimately baseball history.  There is no telling what would have happened had any of these moves taken place.  Would a World Series even have been a possibility without Mo?  Would the Yankees have become the most dominant team in sports if they had signed Maddux, Bonds, and Bonilla instead of Danny Tartabull, Jimmy Key, and Wade Boggs?  There is no way to know but it sure is fun to remember.  Sometimes, keeping the prospect is better than trading him.  We might soon be able to add the Jesus Montero for Cliff Lee trade to this list in a couple of years.  Who knows?