The Captain's Blog

(In addition to appearing at The Captain’s Blog, this post is also being syndicated atTheYankeeAnalysts.)

Some of Brian Cashman's best decisions have involved trades he didn't make.

The trade deadline has resulted in some of the most lopsided deals in history, but that doesn’t mean evey swap made under the gun has to have a winner and loser.  Each year, there are just as many deadline deals that are prudent as ones that are impetuous, but what about the trades that don’t get made? Sometimes, by not pulling an itchy trigger, a general manager can make his team a deadline winner even without making a single transaction.

During his Yankee tenure, Brian Cashman has not been very active during the trade deadline. In fact, when he has made a major in-season deal, it has often come earlier in the year when the pressure of the deadline was off in the distance. What Cashman has been very good at, however, is avoiding impetuous deals that would have a negative impact on the future more than help in the present.

In his first year as GM, Cashman inherited a strong team and built it into a powerhouse with additions like Chuck Knoblauch and Orlando Hernandez. However, despite compiling a record setting winning percentage over the first four months, the Yankees were still front and center amid several rumors at the deadline. In particular, it was reported that the team was close to securing Randy Johnson for a package including Hideki Irabu and a combination of prospects like Ramiro Mendoza, Mike Lowell, Ricky Ledee and Homer Bush.

Although it’s hard to imagine that Johnson would have had a negative impact on the Yankees, an improvement would have been impossible.  Granted, if the deal had been made, the Yankees may not have had to face Johnson in the 2001 World Series, but it’s also possible they wouldn’t have gotten there without the likes of Roger Clemens and David Justice, two players later acquired using players rumored to be in the mix for Johnson.

In 1999, the Yankees reportedly considered trading Andy Pettitte for Roberto Hernandez.

In 1999, Andy Pettitte was having one of his most difficult seasons in the big leagues. During the first half, the normally reliable lefty compiled a 5-7 record with a 5.59 ERA, leading to speculation that the Yankees might trade him before the deadline. One of the more prominent reports involved the Yankees trading Pettitte to the Phillies for two prospects who would then be flipped to Tampa for Roberto Hernandez. Had that trade been made, there not only wouldn’t have been a core four, but it’s also possible the Yankees wouldn’t have had four championships to celebrate. Because of Cashman’s ability to resist the pressure from above to trade Pettitte, the Yankees were able to enjoy 85 more wins, including nine in the post season, from the homegrown left hander.

The next season, the most often discussed Yankees’ target was Sammy Sosa. According to the Daily News, Alfonso Soriano, one of the team’s top prospects at the time, was believed to be the centerpiece of a potential deal that also included names like Ted Lilly, Jake Westbrook and Drew Henson. Had that trade been consummated, the Yankees might have benefited from Sosa’s prolific power, but may have also run the risk of changing the dynamic of the team. The Yankees would have also missed out on Soriano’s fantastic 2002 and 2003 seasons, and been denied the subsequent players acquired in future trades involving those rumored to be in the Sosa deal. Finally, the Yankees would have also been further saddled with Sosa’s steroid baggage, which combined with revelations about Jason Giambi (assuming the Sosa acquisition wouldn’t have precluded the Giambi signing), could have become an even bigger distraction.

In 2005, the Yankees were searching for a center fielder to take over from the struggling Bernie Williams. Their prime target was believed to be Mark Kotsay, but Billy Beane reportedly demanded a package of Robinson Cano and Phil Hughes. Luckily, Cashman resisted the need, opting instead to go with fill-ins like Bubba Crosby. Although that decision would come back to haunt the Yankees in the 2005 ALDS, when a misplay by Crosby contributed to a loss, the Bronx Bombers are currently enjoying the fruits of the players they didn’t trade.

Even before 2005, Cano had been an often rumored component in several earlier deadline deals, but thanks to both prudence, and luck, the Yankees wound up retaining the future All Star. Had he been dealt, the extent to which the Yankees would have suffered is hard to calculate, but needless to say, the organization is more than happy to not find out.

The jury is still out on whether Cashman's decision to pass on Cliff Lee was a good one.

The most recent deadline trade that will be judged on the basis of not going through was last July’s reported acquisition of Cliff Lee for a package including Jesus Montero and either Ivan Nova or Eduardo Nunez.  At various points over the past year, assessment of Cashman’s decision to back away from the trade has run the gamut from a colossal mistake to fortunate reprieve, but only the future performance of the involved components will determine the wisdom, or lack thereof, involved.

This year, the most compelling trade deadline rumor has been Ubaldo Jimenez for a package of the Yankees’ best prospects, including Montero, Dellin Betances, and Manny Banuelos. Cashman only has five more days to determine if such a deal would be in the best interest of the Yankees. Hopefully, he isn’t feeling any pressure. After all, if the deal backfires, it’ll only become a permanent part of his legacy.