The Yankees know: don't sign players until you have to

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It’s safe to say I’ve given up on my hopes of becoming a major league GM. But if a reader hits the lottery, buys a team and decides to give me a shot, know that there’s a couple of rules I’d live by:
1. Never give multiyear deals to bench players
2. Don’t re-sign veterans until it’s absolutely necessary

The Yankees already seem to follow both. No. 1 may be an accident, but No. 2 is team policy: the Bombers don’t negotiate with their free-agents-to-be until they actually become free agents.
Now I’m certainly not against giving long-term deals to youngsters. That strategy has saved major league teams tens of millions of dollars over the last decade, not only in avoiding arbitration hearings and early free agent years with the players that sign them but by holding down the arbitration awards of those that don’t.
But giving veterans long-term extensions when they still have one or two years left under team control is a losing proposition more often than not. The potential gain — saving money over what it would cost to sign the player closer to free agency — just isn’t worth it. More information leads to better decisions, and there’s a lot of information to be gained by waiting that extra year until the player nears free agency.
For one thing, the players getting these extensions are already in their prime and likely at the peak of their value when they sign them. After all, the player isn’t going to want to sell low on himself by signing after a bad year or a rough first half. Teams, on the other hand, have no problem buying high by signing players immediately after a career year.
Look at the Yankees. Obviously, they have a huge advantage in these circumstances, since they don’t have to worry about being outbid in free agency. But they made no attempt to re-sign Derek Jeter and Mariano Rivera last winter. Their policy probably cost them some money when they had to re-sign Jorge Posada as a free agent after his career-year in 2007, but it’s worked out well overall and the team has fewer bad contracts now than probably at any point in the past 15 years.
It’s something the Phillies should have looked at very carefully before committing an additional $125 million to Ryan Howard on Monday. Howard was already signed through the end of next year, and it’s hard to imagine that the Phillies are saving any money over what it would have taken to sign him a year from now. Howard pretty clearly wanted to stay in Philadelphia. Was he really going to turn down $25 million per year next April? Or even next November for that matter?
Ponder that while looking at a few examples of bad deals signed by players under contract and still one to two years away from free agency. I won’t count arbitration-avoiding signings like Detroit’s Dontrelle Willis and Nate Robertson deals, since while I think they fit, they weren’t contract extensions.
Travis Hafner – Indians
Old deal – Four years, $11.5 million for 2005-08 (2008 was a club option)
New deal (Signed July 2007) – Four years, $57 million for (2009-12)

Hafner was maybe baseball’s biggest bargain for two years in 2005 and 2006. The Indians gave him his huge extension even though his play had fallen way off in the first half of 2007, and it’s proven to be a franchise killer since the moment it was signed.
Mark Kotsay – Athletics
Old deal – Three years, $16 million for 2004-06
New deal (signed July 2005) – Two years, $15 million for 2007-08

Hit .214/.279/.296 in 56 games during an injury-ruined 2007. The A’s paid $5 million to get the Braves to take him for 2008.
Eric Chavez – Athletics
Old deal – Five years, $17.65 million for 2001-05 (2005 was a club option)
New deal (signed March 2004) – Six years, $66 million (2005-10)

Seemed like a pretty good idea at the time, and Chavez went on to put up a career-best 898 OPS in 125 games in 2004, so he would have been at least as expensive to re-sign that winter. However, he lost 100 points of OPS in 2005.
Scot Shields – Angels
Old deal – One year, $3.4 million for 2007 (wouldn’t have been a free agent until after 2008)
New deal (Signed March 2007) – Three years, $14.6 million (2008-10)

Shields was worked about as hard as any reliever in baseball from 2004-06, so the Angels were either foolish or simply overly generous for committing to him when they still had him under control for two more years. He went on to have his worst season in 2007, and while he had a fine 2008, he’s contributed nothing since.

Report: Teams have inquired with the Angels about Hector Santiago

ANAHEIM, CA - JULY 20:  Hector Santiago #53 of the Los Angeles Angels of Anaheim pitches during the first inning of a baseball game against the Texas Rangers  at Angel Stadium of Anaheim on July 20, 2016 in Anaheim, California.  (Photo by Sean M. Haffey/Getty Images)
Sean M. Haffey/Getty Images
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ESPN’s Jerry Crasnick reported on Monday that the Angels have received inquiries from multiple teams concerning starter Hector Santiago. He adds that the club is willing to listen to offers. Jon Morosi of FOX Sports and MLB Network reports that the Marlins are among the teams that have inquired.

Santiago, 28, has pitched to a 4.32 ERA with 96 strikeouts and 47 walks in 110 1/3 innings. Sabermetric statistics such as FIP, xFIP, and SIERA think the lefty has pitched even worse than his ERA indicates however, pitting 2016 as his worst performance to date.

Santiago is earning $5 million this season and will enter his third and final year of arbitration eligibility going into 2017.

We also learned earlier that, in an effort to bolster their starting rotation, the Marlins have also shown interest in Wade Miley of the Mariners and Jeremy Hellickson of the Phillies.

Prince Fielder will undergo season-ending neck surgery this week

SEATTLE, WA - JUNE 10: Prince Fielder #84 takes a swing during a game against the Seattle Mariners at Safeco Field on June 10, 2016 in Seattle, Washington. The Mariners won the game 7-5. (Photo by Stephen Brashear/Getty Images)
Stephen Brashear/Getty Images
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The Rangers placed DH Prince Fielder on the disabled list last week due to more neck discomfort. On Friday, Fielder met with Dr. Drew Dossett, who performed spinal fusion surgery on Fielder in 2014 for a herniated disk in his neck. Dossett has recommended another procedure, so Fielder will undergo season-ending surgery this week, Jeff Wilson of the Fort-Worth Star Telegram reports.

Fielder was having a rough season, batting .212/.292/.334 with eight home runs and 44 RBI in 370 plate appearances. He played in only 42 games in 2014, but returned in 2015 looking more like his old self. Unfortunately, neck and back issues are notoriously difficult to fix. Hopefully, this upcoming procedure does the trick for Fielder.

Fielder is owed $24 million per season through 2020, with the Tigers paying $6 million of it per season.