Biggest Contract, 5+ Service Class

Clayton Kershaw, Dodgers: 7 years, $215MM (plus opt-out)

If you’ve read through the prior two posts in this series, the gulf between position-player and pitching contracts really stands out. But hurlers close the gap with vigor once they drawn near to (or reach) the open market. Kershaw’s deal is the largest, understandably, but hardly the only example of a quality starter getting something in the realm of open-market money when entering or in the midst of their final season of team control. Stephen Strasburg ($175MM), Rick Porcello ($82.5MM), and Danny Duffy ($65MM) have all inked such deals in recent years, with Cole Hamels ($144MM) and Homer Bailey ($105MM) scoring notable prior contracts.

Biggest Contract, 5+ Service Class Position Player

Matt Kemp, Dodgers: 8 years, $160MM

Interestingly, it has been quite some time since we’ve seen a 5+ service-class position player land a monster contract. Brett Gardner’s $52MM deal in early 2014 was the most notable since Andre Ethier ($85MM) and Miguel Montero ($60MM) in 2012. For really significant slugger contracts, you have to go back another year, when Kemp and Adrian Gonzalez ($154MM) got big bucks to forego the possibility of yet greater riches in free agency. At the time of his deal, Kemp was a 27-year-old who had just turned in an MVP-caliber campaign. This contract provides a notable marker for some high-quality players currently nearing free agency, should they agree to engage in talks.

Biggest Contract, 6+ Veteran

Miguel Cabrera, Tigers: 8 years, $248MM (plus two options)

In some regards, it’s not worthy considering veterans with over six years of service separately from 5+ players that are still in arbitration. Many (but not all) of the former group are, like the latter, just one season away from free agency. That said, there are some general differences — in particular, all highly-paid 6+ players have already sold at least one would-be free agent season — so we’ll break them out. Age is increasingly a factor at this point, though some 6+ players that agreed to earlier-career extensions have still wrangled new deals at young ages. For instance, Joe Mauer’s $184MM contract was signed before his age-27 season. The number of years on the odometer did not dissuade Detroit from re-upping Cabrera two seasons before his existing contract was set to run out. Questionable at the time, that decision is looking all the more troublesome after Cabrera stumbled in 2017. Other major contracts from this bucket include David Wright (link), Ryan Zimmerman (link), and Dustin Pedroia (link).

Biggest Contract, 6+ Veteran Pitcher

Justin Verlander, Tigers: 5 years, $140MM (plus option)

As noted in our mid-arb post, JV and Felix Hernandez (link) followed parallel paths in market-pacing salaries in each of their two extension situations. Other major 6+ pitching extensions include Johan Santana (link), CC Sabathia (link), and Matt Cain (link). While these contracts show that veteran pitchers nearing free agency can still cash in even as they build up mileage on their arms, age and wear-and-tear factor all the more for hurlers. Contract length, then, has proven somewhat harder to achieve. Cabrera, Mauer, Wright, Zimmerman, and Wright all secured eight-year guarantees, while all the pitchers just named settled for five or six-year terms.

(So, we’ll include Super Two-eligible players in this post. But we won’t yet be looking at those 5+ service-class players who signed as the open market beckoned.)

Typically, a fair number of significant players sign long-term pacts in the period between the start of a new year and the start of a new season. This time last year, we were within a week or so of learning of mid-arb deals for players including Yangervis Solarte, Wil Myers, and Kole Calhoun. Many of this season’s arbitration-eligible players also feature as plausible candidates.

Of course, the need to hammer out an arbitration salary for the coming campaign often helps spur talks. This time around, MLBTR’s Tim Dierkes reports, it seems that all of MLB’s teams will be utilizing a “file-and-trial” approach to arbitration, which could further incentivize multi-year deals — though not necessarily ones that buy out would-be free agent seasons.

On to the most notable deals from the Super Two, 3+, and 4+ service groups …

Biggest Contract, Super Two

Buster Posey, Giants: 8 years, $159MM (plus one option)

This particular contract stands out from the crowd quite a bit. It dwarfs the other large Super Two deal, such as those agreed to by Starlin Castro ($60MM), Jay Bruce ($51MM), and (most recently) Kevin Kiermaier ($53.5MM). Indeed, it tops anything agreed to by players in their 3+ service class as well (see below). And the Posey deal also represents the second-largest deal of any kind ever agreed to by a catcher. There’s a reason for all that, of course: Posey was and is a once-in-a-generation talent at his position. His suitably monstrous deal, then, functions as a notable market marker for any truly elite players engaging in contract talks early in their arbitration eligibility.

Biggest Contract, Super Two Pitcher

Gio Gonzalez, Nationals: 5 years, $42MM (plus two options)

As we saw with the pre-arb extensions, there’s a big gap between what top position players have been able to command and what’s available for pitchers. Teams just have not been willing to promise that much money through arbitration eligibility, even if it means picking up affordable future control. The other top contract in this service class is Jaime Garcia, at a $27.5MM guarantee. Still, as the Nats’ experience with Gonzalez shows, there’s quite some upside to be found even when a team does plunk down a relatively significant promise; he has delivered excellent value over the deal and has had both his options exercised.

Biggest Contract, 3+ Service Class

Freddie Freeman, Braves: 8 years, $135MM

While Freeman couldn’t top Posey, this was still a notable contract. The first baseman was certainly an accomplished hitter, but wasn’t a tremendous power source and was considered limited to first base. Of course, the Atlanta organization was right to trust in Freeman, as he has turned in a 157 OPS+ in each of the past two seasons while showing 30+ home run pop (as well as the ability to play third in a pinch, though we’ve likely seen the end of that experiment). This deal topped the second extension of Ryan Braun ($105MM) as well as large contracts agreed upon with 3+ service class players Kyle Seager ($100MM), Albert Pujols ($100MM back in 2004) Wil Myers ($83MM), and Justin Morneau ($80MM).

Biggest Contract, 3+ Service Class Pitcher

Carlos Martinez, Cardinals: 5 years, $51MM (plus two options)

It seems fair to say that Martinez had established a similar level of productivity as had Freeman to the same points in their career. But his own record-setting deal came in way shy despite the fact that he was only entering his age-25 season. Still, Martinez handily out-earned prior pitchers from this service grouping, such as Ervin Santana (link), Scott Kazmir (link), and Johnny Cueto (link).

Biggest Contract, 4+ Service Class

Giancarlo Stanton, Marlins: 13 years, $325MM (plus opt-out)

The Stanton deal remains the biggest and longest contract yet agreed to by a MLB player, so it more or less sets all the records. The 4+ stage is a popular time to lock up established superstars, but it typically takes a hefty sum to get it done. Ten-year commitments have gone to Joey Votto ($225MM) and Troy Tulowitzki ($157.75MM). Other nine-figure guarantees include the first Miguel Cabrera extension ($152.3MM), the ill-fated Ryan Howard pact ($125MM), and the roller-coaster Elvis Andrus deal ($120MM). Evan Longoria’s $100MM second extension was just traded, with the Rays taking a bit of a haircut but also receiving some talent in return.

Biggest Contract, 4+ Service Class Pitcher

Justin Verlander, Tigers: 5 years, $80MM

Verlander and Felix Hernandez ($78MM) set the bar for mid-arbitration pitchers. The highly accomplished duo performed well enough in the early going under these contracts that each ultimately inked similar, yet more significant extensions. Both have had their stumbles since their newer contracts kicked in, though the former has mostly been in excellent form of late and the latter is at least still fairly youthful (he’ll turn 32 at the beginning of the 2018 season, whereas Verlander is soon to hit his 35th birthday). The only other player in shouting distance is Matt Harrison, whose $55MM deal did not pan out due to a serious back injury. A variety of other 4+ pitchers have inked deals within $5MM or so of a $40MM guarantee, including Dan Haren (link), Josh Johnson (link), Zack Greinke (link), and Chad Billingsley (link). As the names listed here would indicate, it has been quite a while since we’ve seen a significant contract for a 4+ hurler.

Biggest Contract, Mid-Arb Reliever

Craig Kimbrel, Braves: 4 years, $42MM (plus one option)

Kimbrel has long been a super-elite reliever. Indeed, his raw numbers were so impressive that they busted MLBTR’s arbitration model. With some real questions as to just how much Kimbrel might earn in arbitration, the sides agreed to an interesting contract that was utterly without precedent. To that point the biggest reliever extensions of any kind were in the $20MM range (Huston Street (link) and Carlos Marmol (link)). Nothing has approached Kimbrel’s extension since, though ensuing growth in the free agent market for top-end relievers has certainly changed the situation. Indeed, this contract has been traded twice for good value, showing that the Braves did well for taking a risk that no other organization really had before. (Things worked out well for Kimbrel, too: he weathered some relatively lesser seasons without worrying about security and is now poised to hit free agency at 30 years of age, where he might still set new records.)

Last year was no exception, with players such as Danny Duffy, Wil Myers, and Kole Calhoun among those inking extensions in January and others following throughout the spring. In some cases, the pressures of arbitration agreements help to spur broader talks; the Cardinals, for instance, locked up Carlos Martinez for the long run rather than just nailing down a single-season salary.

With another extension season perhaps soon to be underway, it seems like an opportune time to look at some of the top such contracts ever agreed upon. (We did something similar last year with some arbitration records.) Of course, we utilized MLBTR’s extensive extension tracker to produce the results.

All of the above players were at least eligible for arbitration. But some of the most interesting deals occur in situations where a player has yet even to reach the stage in which their salary will begin to rise significantly. In such cases, teams often possess quite a bit of leverage, though the relative lack of MLB track record of those players can perhaps also increase the risk.

Here are a few important market markers for pre-arb extensions:

Earliest Extension

Jon Singleton, Astros: Zero days of service

At some point, this’ll likely become a shared record. For now, though, Singleton is the only player who has ever signed an extension prior to (or, in his case, at the point of) his first MLB promotion. While the contract promised Singleton only $10MM, it gave him both protection and some earning upside, as I explained at the time. While Singleton is still young enough to turn things around, he has not yet panned out at the MLB level, so the deal has worked out quite well for him.

Biggest Contract, Less Than One Year Of MLB Service

Tim Anderson, White Sox: 6 years, $25MM (plus two options)

This contract type was once almost exclusively in the domain of the Rays, who locked up Evan Longoria (link), Matt Moore (link), and Chris Archer (link) to early deals. (Salvador Perez of the Royals is another key example.) But the Sox came through with the most recent, and most lucrative, deal for a player with less than one year of MLB service. Anderson had played for most of a season at the game’s highest level, so it wasn’t as if he had yet to put down any track record there. But it still seemed like a not-insignificant risk for a player with some definite kinks to iron out. Anderson struggled in the first year after signing the deal, though there’s plenty of time for him to make good on it.

Biggest Contract, Between One And Two Years Of MLB Service

Andrelton Simmons, Braves: 7 years, $58MM

Though Simmons never seemed likely to draw massive arbitration salaries, since so much of his value came from his glovework, he still holds the record for the largest deal for a player with less than two years of MLB service. That deal topped Ryan Braun’s longstanding record of $45MM. Most recently, Christian Yelich of the Marlins comes in just behind Simmons with a deal that promised him just under $50MM and also included a club option for an eighth season. While the Simmons contract has since been dealt to the Angels, it continues to be an appealing asset — all the more after his outstanding all-around 2017 season.

Biggest Contract, Between Two And Three Years Of MLB Service (Non-Super Two)

Mike Trout, Angels: 6 years, $144.5MM

This deal stands out, and for good reason: Trout is the greatest player of his generation. No other 2+, non-Super Two players have landed in his stratosphere, though some have secured major guarantees. Carlos Gonzalez ($80MM, Rockies), Hanley Ramirez ($70MM, Marlins), Matt Carpenter ($52MM, Cardinals), Andrew McCutchen ($51.5MM, Pirates), Justin Upton ($51.25MM, Diamondbacks), and Rougned Odor ($49.5MM, Rangers) are among them. Since signing, Trout has continued to reel off otherworldly seasons. The 26-year-old almost certainly would have secured his third MVP award in 2017 had he not been limited to 114 games due to a thumb injury.

Biggest Pre-Arb Pitching Contract

Corey Kluber, Indians: 5 years, $38.5MM (plus two options)

Fair to say there’s some added risk discount baked into pitching deals. Kluber became the latest highly accomplished pre-arb hurler to ink a contract with this same essential structure. The dollars have slowly crept upward over the years, but the early-2009 Jon Lester deal with the Red Sox remains the model. Over the years, Yovani Gallardo (link), Trevor Cahill (link), and Chris Sale (link) are among the starters that took this sort of agreement with over two years of MLB service (but not enough to reach arbitration as a Super Two). It’s not really worth treating the 1+ service class any differently; we’ve seen the same apply there, with Madison Bumgarner earning the largest such deal ($35MM) and pitchers like Julio Teheran (link) and Ricky Romero (link) also checking in with similarly structured contracts. Kluber’s age likely prevented him from truly breaking out of the mold, as he was coming off of a Cy Young campaign when he put pen to paper. Since, he has turned in 640 2/3 innings of 2.98 ERA pitching, locking up his second AL Cy Young nod last season.

Biggest Pre-Arb Reliever Contract

Sean Doolittle, Athletics: 4 years, $10MM (plus two options)

It’s not all that surprising to learn that not many pre-arb relievers have signed extensions at all, let alone that none rank among the largest in the game. Perhaps that will begin to change, though, with the bullpen taking on an increasingly prominent role in game management and top-end arms securing rather massive payouts via free agency (and, in some cases, through saves-fueled arbitration cases). The Doolittle contract has worked out quite well despite his injury struggles and the A’s own disappointments on the field. Oakland swapped the contract to the Nationals last summer, cashing in on the high-powered southpaw at a point when he was in good health and throwing well.

Longest Guaranteed Term, Pre-Arb Extension

Ryan Braun, Brewers: 8 years

Unless there’s a longer prior deal that pre-dates our database and isn’t known to this author — if so, let us know in the comments! — the first Braun extension contained the longest fully guaranteed term given to a pre-arb player. (As noted above, its $45MM guarantee also once held the record for money promised to a 1+ arb class player, but it has since been eclipsed.) There are a few other deals that contemplate potential eight-year terms — utilizing 7+1, 6+2, or 5+3 guarantee/option structures — but this appears to be the only one that gives the player such extensive security for such a long time frame. Astute readers will note that one contract appears to provide for a potential nine-year term: Jose Tabata’s extension with the Pirates, which has widely been discussed as a six-year contract with three options. But that deal was signed in August of 2011 — the same season that must be counted as the first to accept that characterization. While Tabata did receive a modified salary for the season he was then in the middle of playing, the deal covered only eight future campaigns. (As things turned out, of course, the options never even came into play as Tabata’s career fizzled out.)

Photo courtesy of USA Today Sports Images.