Yankees Worst Free Agent Signings All-Time


Yankees Worst Free Agent Signings Number 1

Adam – The crème de la crème of worst Yankees free agent signings has to be awarded to Carl Pavano. The irony here is that one of four other teams, including the Red Sox, could have been the recipient of the “Pavano Years.” The signing looked brilliant for all of one month as he managed an ERA around 3.00 and even threw a shutout.

Soon to follow was an innocent enough injury for a man who had multiple seasons with 30+ starts. That rotator cuff tendinitis and a little shoulder inflammation kept him out for the rest of the 2005 season. Pavano liked his guaranteed contract and the injury train so much he just refused to get off.  He bruised his butt (because we all knew that was a thing) and got in a car accident, in which he hurt his ribs and kept it from the organization until he was about to come back at the end of the 2006 season.

Pavano finally returned to the mound on Opening Day 2007. Now was his time to redeem himself. It was time to let the injury bygones be bygones and earn his money. Well two starts later, the injury train stopped by and Pavano climbed on with a UCL tear. Tommy John surgery and many months later, he returned at the tail end of 2008. He did make seven consecutive starts but a 5.77 ERA meant he was probably better off staying injured. While not complete, the Yankees did get a measure of revenge when a healthy Pavano pitched against them twice for the Twins in the ALDS and was rocked. A fitting end for a guy that is marked as number one on the Yankees worst free agent signings list.

Rich –  Carl Pavano is my choice for the worst free agent signing in Yankees history.  The Yankees won the services of Pavano after a heated free agent battle with many teams including the Boston Red Sox and the Detroit Tigers.  They signed him to a four-year, $39.95 million contract.  His first month was pretty good, but then injuries happened, and they never seemed to stop.  Pavano suffered rotator cuff tendonitis, bruised buttocks (seriously), got into a car accident that he didn’t tell anyone about and injured his ribs, and then when he finally did come back he suffered a UCL tear.  All told, Pavano made 26 starts for the Yankees over three years, going 9-8 with a 5.00 ERA in 145.2 innings.  The Yankees basically paid Pavano over $500,000 per start and those starts, overall, were not very good whatsoever.

Yankees Worst Free Agent Signings Final Thoughts

Rich –  Free agency in MLB is a crap shoot.  Sometimes teams will strike gold, but, usually, teams miss.  You hope a player gives the team great production initially and then the team is willing to eat the contract in the last few years.  Signing players like Reggie Jackson are great when it happens – ride a future Hall of Famer as long as you can and win as much as you can while he is with you.

Signing a player like CC Sabathia is pretty good – win a World Series immediately and then hope you get at least fifth starter quality from him when he’s at the end of his career and contract.  However, most signings are for free agents that had career years immediately before signing a big deal, never to live up to those numbers again, or they sign a player that cannot stay healthy, but because of the financials of the deal, there is not much the team can do (thankfully, the Yankees can absorb more of these types of deals than some “smaller market” teams can).  The great free agent signings are remembered forever, however, so are the bad signings.  The Yankees have plenty of bad signings in their history (the ones listed previously plus deals like Spike Owen in 1992 or Jaret Wright in 2004) but these five take the cake.

Adam – Free agency can be scary for any team and fan base but it is part of the game. People always believe player X is a lock or player Y stands no chance of returning on the investment. Sometimes teams overpay for a position of need and other times it is a deal too good to pass up. A return on investment can mean many things. Oft times they hope for short-term success and are flushing the money on the back end of a contract (see CC Sabathia).

The Yankees are not immune to free agency misses. You can point to Spike Owen, the one to solidify shortstop before Derek Jeter. There are signings like Jose Contreras, Jaret Wright, Alex Rodriguez, Danny Tartabull, and many others depending on your personal criteria. But the five I listed are the Yankees worst free agent signings in my book. What about you?

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Andrew Farelli

Where’s AJ Burnett?


People didn’t pick Whitson or tartabull because they didn’t know who they were

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