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.

Eric Hosmer’s eight-year, $144 million contract isn’t that bad

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Late Saturday night, Kevin Acee of the San Diego Union-Tribune reported that the Padres and first baseman Eric Hosmer agreed to an eight-year, $144 million contract, the new largest contract in club history. According to Bob Nightengale of USA TODAY Sports, the contract includes an opt-out after the fifth year. Further, Hosmer will average $21 million per year for those first five years and $13 million for the final three years, so it’s severely front-loaded.

Hosmer, 28, had a career year last season, playing in all 162 games while batting .318/.385/.498 with 25 home runs, 94 RBI, and 98 runs scored in 671 plate appearances. Per Baseball Reference, Hosmer accrued 4.0 Wins Above Replacement, only one of six first basemen to do so. At No. 6, he was 0.4 WAR behind Anthony Rizzo and 0.4 WAR ahead of Logan Morrison.

Wil Myers had previously told the Padres he would accept a position change if the club were to sign Hosmer. He will be moving to the outfield as a result. The Padres now have a logjam in the outfield, so Jose Pirela could move moved to the infield. How the Padres plan to handle that situation remains to be seen.

The general consensus about the Hosmer signing once news broke was that it is laughably bad. Back in November, Dave Cameron — ironically now in the Padres’ front office — called Hosmer a “free agent landmine.” That thought hasn’t really changed among many writers. For example, using restraint, Dennis Lin of The Athletic calls the deal “a big gamble.” MLB Network’s Brian Kenny said Hosmer has at least three “red flags.”

FanGraphs projects the Padres to finish 71-91, so adding Hosmer isn’t likely to transform the club into a contender on his own. That being said, the Padres’ payroll was only at $70 million prior to the Hosmer signing, so the contract won’t hamstring them going forward. If the young nucleus of players — including Manuel Margot and Hunter Renfroe — perform as expected, the Padres could be a threat in the NL West relatively soon with plenty of cheap, cost-controlled players and having some experienced veterans like Hosmer and Myers could be useful for their intangibles — pennant race/playoff experience, clubhouse presence, leadership, etc.

Hosmer has had three seasons of 3.5 WAR or more, according to Baseball Reference. He’s had four between -0.5 and 1.0. Now entering his age-28 season, it’s hardly a guarantee he’ll be an All-Star-caliber player in 2018, let alone in 2022 when he is 32 years old. From a strict dollars-to-WAR standpoint in a complete vacuum, one could’ve done better than Hosmer at eight years, $144 million.

The Padres, however, aren’t a small market team; they just operate like one. Forbes valued the club at $1.125 billion last April. The Padres don’t have the financial muscle of the Dodgers or Yankees, but paying Eric Hosmer $18 million on average for the first five years of his contract won’t come close to hurting the organization in any way, shape, or form. More importantly, signing Hosmer shows the rest of the team and the fans a commitment to being legitimate, bumping the payroll up towards $90 million. That now dwarfs teams like the large-market Phillies, who opened up spring training with just over $60 million in player obligations.

In the grand scheme of things, the Hosmer signing is also a good sign given the standstill in the free agent market. Many veteran players — even reliever Fernando Abad, who posted a 3.30 ERA last season — had to settle for minor league contracts instead of guaranteed major league deals. Many others, including the likes of Jake Arrieta and J.D. Martinez, remain unsigned. The rumor that Hosmer wanted more than seven years and close to $150 million was laughed at last month. Agent Scott Boras was still able to get his client the deal he wanted, which could bode well for those still teamless. Martinez’s patience may yet be rewarded like Hosmer’s was; money may once again start flowing in the free agent economy.

In summation, the Eric Hosmer contract is good if: you are Eric Hosmer, related to or a friend of Eric Hosmer, a teammate of Hosmer’s, Scott Boras, a current or soon-to-be free agent, a Padres fan, and a baseball fan in general. The Hosmer contract is bad if: you are a penny-pinching owner of a Major League Baseball team, or someone who cares more about $/WAR than an actual good product being put on the field.