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Jacoby Ellsbury (OF, Yankees)

7 years, $153,000,000

When the Yankees signed Ellsbury away from their rival Red Sox back in 2013, they were still very much the “big-money” Yankees we knew them as for so long. So a splash deal for a 5-tool outfielder didn’t seem too far fetched. Unfortunately, Ellsbury’s seen action in just 520 out of a possible 743 games in New York due to injury. When he’s healthy, he’s still fairly productive, as he’s averaging 27 doubles, 13 homers, 62 RBIs, and a .264 average in 4 years.

Furthermore, he has no timetable for return from his foot/hip injury, while his contract runs through 2020, with $68,428,571 due. He’ll be 36-years-old when it’s all said and done, having earned a little more than $175M over 15 seasons.


Chris Davis (1B, Orioles)

7 years, $161,000,000

After serving a 25-game suspension at the end of the 2014 campaign for PED use, Davis exploded in his contract year (2015), posting 31 doubles, 47 homers, 117 rbis, a .262 average & a whopping .923 OPS. The Orioles couldn’t resist but to bring him back on a long-term deal. Unfortunately, that hasn’t exactly panned out as they might have hoped.

Davis’ production has been rapidly declining each year since the signing, culminating with a first half this year of 7 doubles, 9 homers, 28 RBIs and a ripe .158 average. He’s due another $127M through 2022, when he’ll be 36 years old.

Of the 273 batters who qualify for our True Value Rating, Davis is the worst value in MLB.


Jeff Samardzija (SP, Giants)

5 years, $90,000,000

Samardzija was 30 when he joined the Giants back in 2016, his 4th ML team. His inconsistency kept him from locking in a deal of $20M+ as most starting pitchers were able to do, but even at $18M a year, he rings is as our 3rd worst-value starting pitching in baseball.

Since joining SF, he holds a 4.33 ERA, 1.2 WHIP, and a 22-31 record, including a league-worst 15 losses in 2017. He currently carries an ERA north of 6, and has allowed more earned runs (31) than he as strike outs (30). He’s set to earn $54M through 2020, when he’ll turn 35-years-old.


Miguel Cabrera (1B, Tigers)

8 years, $248,000,000

When the Tigers penned Cabrera to this extension, the then 31-year-old was in year 6 of an 8 year $152M contract. He’s now in year 3 of this new 8 year deal, and coming off his worst season to date in 2017. Toss in a hamstring injury early in 2018, and the fact that he’s 35-years-old, and the future is likely going to be a struggle for Cabrera - and the Tigers payroll. He’s due guaranteed salaries of $30M through 2021, then $32M thru 2023. The deal also includes back to back vested options of $30M in 2024 & 2025, but he’ll need to be a Top 10 MVP player to see that pay, highly unlikely at age 40.

No matter how this plays out, when it’s all said and done come 2024, Miguel Cabrera will have earned nearly $412M across 20 MLB seasons.


Jason Heyward (OF, Cubs)

8 years, $184,000,000

The Cubs were in the midst of a youth rejuvenation, with stars like Rizzo, Bryant, Baez, & Russell rising up the ranks and showing immediate success at the professional level. So a veteran free agent signing (away from division rival St. Louis) made a bit of sense - but not to this degree. Heyward has been an A+ defender, with a solid B- bat throughout his career, but hit the free agent market with an uptick of production for the Cardinals in 2015 (33 doubles, 13 homers, 60 rbis, .293/.359/.798 split).

A $23M per year contract for a player like this would be tolerable were it of a much shorter term, with a club option or two to boot. But the only restriction built into this deal is a PLAYER option for 2019. Heyward, who’s already reeled in $78M from this deal, stands to make another $106M should he continue on with this deal, a move he’s certain to make. And while the power hasn’t resurfaced since joining the Cubs, he is showing signs of turning the corner at the plate in terms of efficiency, as his .285 batting average is 50 points higher than where it was 2 years ago.

Heyward will be 33 when this deal expires, and could conceivably add-on to the $204M he’ll have earned by then.


Giancarlo Stanton (OF/DH, Yankees)

13 years, $325,000,000

It should be said right out of the gate that the Marlins are responsible for the terms of this contract, but somehow found a way to trade a player who had $295M remaining on his deal, but the young Yankees had room to go big on a player who can fill up the power stat lines.

Stanton’s 2017 numbers were ridiculous (32 doubles, 59 homers, 132 RBIs, .281/.376/1.007 slash), so it’s easy to see why teams were clamoring to acquire the 28-year-old. And with a loaded Yankees lineup already in place before he got there, It’s also easy to understand why Stanton’s 2018 numbers likely won’t match his 2017 production (on pace for 32 doubles, 39 homers, .278/.346/.864 slash).

Statistically speaking, right now, overpaying for a player of Stanton’s caliber is fine. The problem with this contract is both the length, and the lack of team control. Stanton is under contract through 2027 (when he’ll be 37-years-old), with a team option in 2028. The deal also includes a full not trade clause PLUS a player opt-out after the 2020 season.

Assuming he opts-in, Stanton will make $96M after the age of 35, including $10M to go away in 2028.