We have already looked at the record-setting pre-arbitration and mid-arbitration extensions. Today, we’ll turn to those contracts that were struck with players who had already reached their final season of team control, as well as those that were agreed upon with veterans who had already moved past six years of MLB service (even if they had multiple contract years remaining at the time of the deal). You can explore more contracts beyond those we’ve covered with MLBTR’s Extension Tracker.
Biggest Contract, 5+ Service Class
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
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
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
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.