19 free agent contracts guaranteeing three or more years have already been signed this offseason, matching the high from the previous five offseasons.  With Ervin Santana, Matt Garza, Ubaldo Jimenez, Stephen Drew, and Nelson Cruz still on the market, it seems likely we'll ultimately see 20 or more deals of three or more years in this 2013-14 offseason.  However, if recent history is a guide, one or more of these players will be left standing without a chair.

Here's a look at the number of contracts for three or more years signed in each of the past five offseasons:

• 2012-13: 19
• 2011-12: 11
• 2010-11: 17
• 2009-10: 8
• 2008-09: 13

Please note that international free agents, typically from Japan or Cuba, have been excluded from this exercise since they often operate on different timelines than traditional free agents.

Of the 68 free agent contracts guaranteeing three or more years from the past five offseasons, 13 were officially signed in January or later (19.1%).  Of those 13, nine were clients of the Boras Corporation, including big money players like Prince Fielder, Adrian Beltre, Matt Holliday, Mark Teixeira, and Derek Lowe.  Agent Scott Boras has a reputation of waiting out the market, and it has served him well in many cases.  While my early November projection of a four-year, $48MM deal for Boras client Stephen Drew seems unlikely at this point, I never viewed Kendrys Morales as likely to get a third guaranteed year.  Though the current market for Drew does not seem robust, I still expect Boras to get at least three years for him.

Since the 2008-09 offseason, only four free agents not represented by Boras have received contracts of three or more years in January or later: Edwin Jackson, Nick Swisher, Jason Bay, and Milton Bradley.  The deals for Jackson and Swisher were actually agreed upon prior to Christmas 2012 and announced officially on January 2nd and 3rd, respectively.  Similarly, the Mets' deal with Bay was reached on December 29th, 2009.  In the last five offseasons, Milton Bradley is the only non-Boras free agent to actually agree to a free agent contract of three or more years in January or later (January 5th, 2009).  Bradley's deal was done by ACES.

If you're a free agent who expected at least three years at the outset of the 2013-14 offseason, and you're not represented by Boras, this trend has to be troubling.  Specifically, the spotlight is on the agents for Ervin Santana (Bean Stringfellow), Matt Garza (Nez Balelo), Ubaldo Jimenez (John Courtright), and Nelson Cruz (Adam Katz).  If any of these four fail to get at least three years, their agent has failed to meet expectations.

As has been widely discussed, Cruz is in a perilous situation.  We don't know what offers the 33-year-old slugger has received to date, but he's tied to draft pick compensation and seems light on current suitors.  Way back in October while working on Cruz's free agent profile for MLBTR, Steve Adams pitched a two-year, $26MM prediction to me and it sounded about right at the time.  Enough information came out in the week following that both of us felt good about Steve's ultimate three-year, $39MM prediction.

In late November, after fellow Biogenesis-connected free agent Jhonny Peralta signed a surprisingly strong four-year, $53MM deal, Jon Heyman of CBS Sports heard from sources that Cruz was "said to seek about $75 million over four years."  While starting negotiations at four years was a plausible tactic in November, an average annual value approaching $19MM never seemed realistic.  Nearly two weeks later, on the first day of the Winter Meetings, ESPN's Buster Olney tweeted that the Rangers were comfortable with a two-year deal for Cruz, while he sought three from them.  Now we're in early January, and I'd bet against Cruz getting a third year from any team.  While a two-year deal may be viewed as underwhelming for Katz, it's worth noting that he doesn't control the ebb and flow of media and fan expectations, and it's possible Cruz never received a reasonable three-year offer.  Katz presumably did have a strong hand in Cruz's decision to turn down the Rangers' qualifying offer in November, which will be questioned if the outfielder falls short of Steve Adams' original guess of two years and $26MM.

There's a good reason why Santana, Garza, and Jimenez remain unsigned, and his name is Masahiro Tanaka.  Tanaka outranked all three in my top 50 free agents rankings published November 4th, and factors related to the revised Japanese posting system delayed the 25-year-old's true entry into free agency until the day after Christmas.  During the 2011-12 offseason, bids were due for Yu Darvish by December 14th, and the situation didn't stop C.J. Wilson and Mark Buehrle from signing strong contracts before then.  It was much more cut and dry with Darvish — the Rangers were revealed as the high bidder on December 19th, and all other interested parties could move on.  With Tanaka, it seems likely more than 20 teams pledged the newly-capped posting fee of $20MM, paid only by the club that signs the pitcher after a standard free agent free-for-all.  The process does have an end in sight, with a January 24th deadline in place.

Back in 2011, the Angels and Marlins had not been connected to Darvish prior to their signings of Wilson and Buehrle.  Conversely, Tanaka seems to be Plan A for many teams, and the would-be contenders that miss out on him probably will turn to Santana, Garza, and Jimenez.  The Diamondbacks, Blue Jays, Yankees, Angels, and Mariners can't all get Tanaka, and it's possible none of them do, so demand could be strong for the Plan B trio even as the calendar turns to February.  Santana and Garza were expected to easily exceed Ricky Nolasco's four-year, $49MM deal (agreed to prior to Thanksgiving), while Jimenez seemed to have a good shot at a similar contract.  I'm sure their agents are unhappy about the way things have unfolded, and there's always a chance the bottom drops out on one of the three pitchers as budgets become settled and we approach time for pitchers and catchers to report in mid-February.  

In the end, there's room for good starting pitching on most teams, plus Tanaka could sign before January 24th.  I still expect Santana, Garza, and Jimenez to receive deals of three or more years, even though there's no precedent from the last five offseasons.

33 players from MLBTR's Top 50 Free Agents list have signed, and with ample time remaining in the offseason, regulars are difficult to come by at most positions.  Let's take a closer look.

• At catcher, Brian McCann, Carlos Ruiz, Jarrod Saltalamacchia, A.J. Pierzynski, and Dioner Navarro have found homes with contracts worth at least $8MM.  Additionally, the Rangers have assembled their tandem behind the dish by re-signing Geovany Soto and adding J.P. Arencibia.  No starting catchers remain in free agency.  Cuban catcher Yenier Bello will likely become a free agent soon, but it's unclear whether any teams view him as a potential regular.
• At first base, Jose Abreu, Mike Napoli, James Loney, Justin Morneau, Garrett Jones, and Corey Hart have signed.  The key remaining free agent here is Kendrys Morales, who has draft pick compensation attached and has not played 500 innings at first base since 2009.  Though the draft pick may continue to scare teams off, there is certainly a price at which some should be willing to surrender one to sign Morales.  The idea of the Scott Boras client as a regular first baseman is dicey, though.  Players like Kevin Youkilis, Mark Reynolds, Michael Young, and Casey McGehee are imperfect solutions as regular first basemen, but they at least merit consideration.
• At second base, Robinson Cano, Omar Infante, Alexander Guerrero, Rafael Furcal, and Mark Ellis are off the board, as well as Kelly Johnson, Willie Bloomquist, Skip Schumaker, and Nick Punto.  36-year-old Brian Roberts looks like the closest thing to a regular on the free agent market, and he hasn't played 80 games since '09.
• At shortstop, Derek Jeter never reached free agency, and the Cardinals signed Jhonny Peralta for $53MM.  Another Boras client with draft pick compensation attached, Stephen Drew, remains unsigned.  If Morales and Drew wind up with disappointing contracts, expect Boras to ramp up his public disgust with the qualifying offer system.  One wild card at shortstop is Cuban Aledmys Diaz, who will be eligible to sign as of February 19th.  Another Cuban name to watch is the defensive-minded Erisbel Arruebarruena.
• At third base, Juan Uribe resembled a regular, and he has re-signed with the Dodgers.  Young might be considered a possible regular at third base after tallying almost 900 innings there in 2013.  McGehee, Youkilis, and Reynolds could be options for some teams to play semi-regularly at the hot corner, as well as Eric Chavez.
• We won't list all the corner outfielders who have signed, but teams seeking a starter in right or left field do have options in free agency.  Shin-Soo Choo and Nelson Cruz are still looking for homes and are viewed as difference-makers.  Raul Ibanez hit 29 home runs and played over 800 innings in left field, so he might be viewed as a regular corner option by some teams.
• Top center field option Jacoby Ellsbury has signed.  While Choo played center in 2013, most teams view him as a corner guy.  A healthy Franklin Gutierrez could re-emerge as a regular in center field, but that seems like a long shot.
• Among DH options, we have Morales and Ibanez.  We heard last month Lance Berkman is leaning toward retirement, though nothing is official.
• In terms of clear regulars, the current free agent market features just five players: one shortstop in Drew, two corner outfielders in Choo and Cruz, and two DH options in Morales and Ibanez.  

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