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Extension can wait? Why Adrian Gonzalez extension might not make sense right now 12.05.10 at 7:06 am ET
By Alex Speier

The Sox will want Adrian Gonzalez for years to come...but might want to wait on an extension. (AP)

The big fish is on the hook, and now needs only to be reeled in. Or does he?

The Red Sox made their trade to acquire star first baseman Adrian Gonzalez on Saturday, giving up the richest package of prospects they’ve parted with since they sent Hanley Ramirez to the Florida Marlins as the headliner in the Josh Beckett deal. It’s a landscape altering deal in many respects, but as much as the Sox love Gonzalez, they were not going to agree to such a rich prospect package without the opportunity to have an exclusive negotiating window to talk to the slugger and his agent about an extension.

Since GM Theo Epstein became the head of baseball operations in late-2002, the Sox have almost always used their key chips to get players whom they would have under contract for more than one year. That has been especially true in recent years, when the team acquired Victor Martinez and Jason Bay for two seasons of control. In ’09, when the team was discussing dealing a number of its best minor leaguers for players like Martinez, Gonzalez, Roy Halladay and Felix Hernandez during the season, it was in part because all of those players would have impacted the Red Sox in at least two seasons.

The Sox are not going to give up their top pitching prospect (Casey Kelly), their top power hitting prospect (Anthony Rizzo) and one of their top defensive prospects (Reymond Fuentes) without getting Gonzalez for several years. But, of course, the Sox have the negotiating window with Gonzalez, so they can do precisely that: Talk with the player and his agent in order to make sure that the two sides see eye to eye on his value, thus allowing the team to secure the 28-year-old’s value for the next several years.

But in at least some respects, the best course the team can take might be to agree with Gonzalez to the parameters of a deal right now, and then wait until, say, April 8 (the day of the Fenway opener against the Yankees) to announce it.

Disclaimer: This scenario is entirely speculative. But there was, at the least, this intriguing tweet from Jon Heyman of SI.com late on Saturday night:

“[The Red Sox] may be willing to do [a Gonzalez] deal without extension and may actually prefer to just talk parameters now, then watch him in spring,” Heyman wrote.

The right shoulder, on which Gonzalez underwent surgery in October and that will keep him from playing until spring training, could serve as the ostensible justification to delay a deal. The Sox could say that they simply want to see the slugging first baseman back on the field and healthy before they formalize the extension. But no one involved in the deal appears to think that the shoulder will actually be a significant concern going forward, and multiple reports suggested that Gonzalez’ physical went without a hitch on Saturday.

The real reason why the Sox might want to wait until after the start of the regular season to announce an extension, if at all possible, is financial. Specifically, the luxury tax implications for the timing of the announcement of a long-term deal are huge.

Right now, Gonzalez is slated to play the 2011 season for a bargain basement $6.2 million option. That salary would give the Sox tremendous financial flexibility to address other needs, most notably, to dip their toes in the water and gun for another big offseason kahuna, namely an outfielder along the lines of Carl Crawford or Jayson Werth.

But, for the purposes of calculating the competitive balance tax (CBT) on the Sox’ 2011 payroll, Gonzalez’ contract would no longer be calculated at $6.2 million if he signs an extension before the start of the season. Let’s say that the Sox are able to sign Gonzalez to a six-year, $132 million extension to run from 2012-2017, after the expiration of his current contract. (Again: purely speculative numbers.)

For luxury tax purposes, Gonzalez’ option and the extension would be added together. So, he would be viewed as receiving a seven-year, $138.2 million deal, with an average annual value of $19.74 million per year.

The implications would be significant. The Sox have always viewed their CBT payroll as being more significant than their actual payroll, and with good reason: If they can avoid doing so, they don’t want to pay the luxury tax.

The Sox did exceed the $170 million luxury tax threshold in 2010; every dollar they spent beyond that sum will be taxed at a rate of 22.5 percent. In 2011, the tax rate will rise to 30 percent for every dollar they spend beyond the $178 million threshold outlined in the Collective Bargaining Agreement.

If Gonzalez is playing under the terms of his current contract, it would go a long way towards helping the team avoid paying the tax in 2011. Superstar production for a $6.2 million CBT can help transform a payroll.

But if the Sox sign Gonzalez to an extension now, the team would have an additional $13.5 million in taxable payroll (again, as calculated for luxury tax purposes). That would make it very difficult — indeed, almost impossible barring a move to shed payroll — for the team to sign a Werth or Crawford while staying under the luxury tax threshold of $178 million. That, in turn, could cost the Sox over $4 million in luxury tax money. (Under a six-year, $132 million deal, it could be as much as $4.05 million.)

So what does that have to do with signing the extension after the season starts? If the extension is signed after Opening Day rather than before it, then it would not be factored into the calculation of Gonzalez’ AAV for the 2011 season. So, he would have a $6.2 million CBT hit in 2011, and then count for $22 million (or whatever the average salary is of his long-term deal) against the luxury tax threshold during the life of the extension. Under that scenario, the Sox could likely afford to hand out a monster contract to Werth or Crawford while still limbo-ing under the luxury tax threshold for next year.

Keep in mind that the Sox have frequently gone to such lengths in order to minimize their luxury tax hit. A few examples:

– The team structured its one-year, $10 million deal with Adrian Beltre to ensure that he would only count for $7 million against the CBT.

– The team waited to announce extensions for Coco Crisp (2006 for the 2007-09 seasons), David Ortiz (2006 for the 2007-10 seasons) and Josh Beckett (2010 for the 2011-14 seasons) until after the start of the season so that they would be able to minimize their luxury tax hit.

(A footnote to this idea: The Sox would, of course, be increasing their luxury tax hit for the 2012-17 seasons in this scenario, from $19.74 million to $22 million. But: 1) No one knows what form, if any, the luxury tax will take in the next Collective Bargaining Agreement, which is currently open to negotiation between players and owners; 2) The extra $2 million and change represents a fairly small increase; and 3) The Sox will have contracts for J.D. Drew ($14 million AAV), David Ortiz ($12.5 million), Jonathan Papelbon (approx. $11 million), Mike Cameron ($7.75 million), Marco Scutaro ($6.25 million), Tim Wakefield ($2 million) and Jason Varitek ($2 million) coming off the books after the 2011 season. That is a mind-boggling $55.5 million coming off the books for luxury tax purposes.)

All of that being said… It should surprise no one if Gonzalez and the Sox announce by 2pm EST on Sunday (the deadline for the negotiating window, as reported via twitter by Ken Rosenthal FoxSports.com) that they have a deal in place. This is a marriage that both parties want to enact.

BUT, if there is not an extension, it is far from a worst-case scenario for the Sox. You may hear statements suggesting that the sides are close, but that they wanted to get to know each other a bit better, and to see where Gonzalez’ health stands entering the season. But the reality is that if the Sox and Gonzalez don’t have an extension officially in place, it may just be a matter of waiting for the start of the regular season to announce it so that the team will maximize its financial flexibility to pursue other deals this offseason.

Read More: adrian gonzalez, cbt, luxury tax, payroll Print  |  Email  |  Bark It Up!  |  Digg It
  • Joe

    This is all well and good for luxury tax purposes and whatnot. But what about the risk associated with doing the deal and then Gonzalez might say ” I want to test free agency.” Teams like the Angels, Dodgers, Cubs, Rangers, etc. might drive his price even higher than the amount possibly lost to luxury tax. What if his deal is $20 million a season now (or his demand at least) and say $25 million to the Sox or another team later? If he is willing to agree to a handshake deal now and sign later, fine (which I wouldn’t do if I am him either, what if he has a problem with his shoulder or it heals slowly, I wouldn’t want to risk my position if I am him). If I am them, I would rather risk the luxury tax now rather than having to possibly pay him even more over the length of an extension or worse, lose him completely.

  • Ozzie65

    I don’t buy the Luxury Tax theory. It makes no sense to give up what we’d be giving up to get Gonzalez here without a long term deal locked in. I agree with Joe’s comments.

  • keith

    You know what gonna happen gonzalez will hire boras and only stay here for a year.

  • Ryan

    All well and good, but YOU DO NOT TRADE KELLY AND RIZZO without the extension being FINALIZED. Don’t even do the deal until April if your goal is to avoid the Lux Tax. Do not trust any handshake deals or anything like that when you are giving up three of your top six prospects.

  • Robert

    They are going to allow a 4 million luxury tax to stand in the way of 1: tying him up long term so as to not have to worry about losing him, 2: allow a 4 million dollars tax to stand in the way of adding another piece such as Werth? Same old Red Sox. Penny wise,pound foolish.If you bring in AG without adding another premier bat,whats the point.AG himself, is not enough to win it all. You might as well hang on to Kelly and the others.If they want to play it cheap, there is Laroche, Overbay, and others,or just keep Beltre who wants to play here.I understand the concern about his shoulder, but if thats the case, why not wait untill the trading deadline? This has got John Henry written all over it.Terribble owner!

  • Jeremy

    Alex

    I thought that for CBT purposes, the AAV going back to his original contract date is what the Sox would pay. So, he signed a 5 year/15mm contract. Wouldn’t that make his AAV $3mm for the Sox? If the Sox are being charged $6.5mm for CBT purposes, then his CBT based salary would exceed his total salary (Padres @ 3mm/year for 4 years + Sox at 6.5mm/year for 1 year = 18.5mm vs his contract of 15mm).

    Just curious.

  • Ravi

    I don’t think Alex is suggesting they SHOULD go this route, just that it’s a possibility. And it isn’t $4million that would stand in the way of the deal. Every consecutive year a team goes over the tax, the rate they are taxed increases, so if the Red Sox are going over the tax for the years of the Gonzo deal, they’d rather have it start at the lowest tax, rather than the 30% they’d be taxed. I do not think Epstein and the Red Sox ownership would make this trade without getting an extension.

  • StuAndrews

    I am guessing that at least two of the prospects end up being real good, sox could have signed VMART for a lot less and he could have caught for two years and then moved to first.

  • Fisk

    VMart is older and isn’t even close to the same quality of hitter or fielder that AGonz is. The difference is much more than the two prospects.

  • Andrew

    Don’t worry, I am pretty sure there will be a deal before 2 PM today.

  • Paul

    Do it now!!!!!!

  • http://Enteryourwebsite... M.C.

    I hate this trade, another instant gratification move. Top-flight pitchers are much rarer than top flight bitters. Keep Kelly.

  • Zavon Hines

    Twever is a moron.

  • ntarmon

    Sign a contingent contract. Since there is a condition precedent, that the contract does not come into full effect until the player passes medical scrutiny and plays his first game, the agreed upon extension, in writing, is not a material fact, until that condition precedent comes into effect the first day , the first month of the season.

    Doing this binds the player, at the club option, and gives the club the out, so that for cap purposes the sign contingent contract can not be counted against the cap.

    What about a club option at the end of the first year contract for a term of years at $22 or does that not skirt CAP rules?

    Moreover, even though the PADS would not agreed, make a provision that if an extension is not signed by May they must pick another 2 top 10 BA talent, not named iglesias, renaudo or kalish.

  • marchhare

    The phrase “penny wise and pound foolish” comes to mind. Saving the luxury tax is no small matter, but would you really want to risk everything that went into this deal for a few million dollars?

  • http://weei.com/blogs Jared vartiek turcotte

    WE HOPE THE DEAL WILL NEED TO BE IN PLACE BEFORE 2pm TODAY.. FOR AGONA CONTRACT EXTENTION I THINK WILL BE a 8 YEARS DEAL or 6 SIX CONTRACT EXTENTION IS ALMOST 2pm buddy UPDATE WILL CONE SOON.

  • redsox4life

    The majority of the posts on here are completely ridiculous and ignorant. One says this deal is an “instant gratification” deal. We’ve been after Agon for years, hows that instant gratification? Everyone crying about prospects? Thats all they are is prospects. Kelly has struggled in Double A and is currently struggling in the winter leages. Its like the stock market you morons, you buy longterm consistent stocks, not low price hope and dream stocks. Everyone is so worried about another Hanley Ramirez developing. Agon is a top five hitter coming to Boston. And to top it off you think for one second Theo does this trade without a contract in place? He’ll wait till opening day and save on the luxury tax. Its business people, come on! If you dont get it, its probably because your working at a gas station or flipping burgers and luxury tax is a foreign language to you.

  • http://www.thomasaquinas.edu Ryan

    Come on, Alex, you shill. Tell us how your beloved Theo made the right move in letting Gonzales walk. Tell us what the numbers say. And tell us again how Josh Beckett is a confirmed workhorse. Wish I could get paid to write what you write. Unbelievable.

  • Name: Mark

    Theo has a recent history of wanting short contracts, ie Bay, Martinez. Since the contract is just now being written, it should be limited for 2010 to the 6Mil range, not heavily effecting negotiating position for other trades this year. So, length of contract is probably the hangup. When you are in the 50% tax bracket, it doesn’t make too much diffence to delay payment some.

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