Ranking the 10 worst contracts in the American League East

Remember, “bad contract” does not equal “bad player.” “Bad contract” also does not equal “bad contract right now,” Yankees fans.

The American League East is a behemoth division that features three of the league’s biggest spenders, as well as the Rays and Orioles, who’ve reached varying levels of contention (to say the least) without so much as lifting a pen since 2014.

Wander Franco, you ARE a Ray (until your costs begin to escalate).

The Yankees, Red Sox and Blue Jays, though? They know how to shell out coin, though Boston has been a lot more judicious about doing so in the Chaim Bloom Era for their homegrown talent, specifically. Coors Field shortstop? Pay the man! Beloved hometown shortstop? Dilly dally!

This roundup of the division’s worst deals takes into account changing tides and future performance, but it’s not airtight. My No. 7 may be your No. 4, and you know what? I’ll nod my head and accept that.

Of course, two of these folks are no longer in the division, but their paychecks live on. In some ways, that might be the worst deal of all.

HONORABLE MENTIONS: Josh Donaldson’s two-year deal (because even though he’s been productive, if he’s going to bring controversy too…), plus Aaron Judge’s and Rafael Devers’ future mega-deals (still unsigned).

NOTE: “Remaining” includes 2022’s salary.

10 Worst Contracts in the AL East — Yankees, Red Sox, Blue Jays…

10. Giancarlo Stanton – 6 Years, $179 Million Guaranteed Remaining

Yankee Homer Alert? Yes. Sure. A little. But over the past year, the 32-year-old Stanton’s narrative has swung so significantly his cost has become underrated by Yankees Despisers.

As 2021 opened, Stanton was a “lifelong DH” struggling to overcome his swing-and-miss prowess to make the impact he’d always desired in the Big Apple. Now? He’s coming off a career-redefining campaign in the clutch (sometimes, it’s all timing), and with Judge’s new contract approaching this offseason, Stanton’s average AAV of under $30 million for his remaining six seasons in the Boogie Down looks like a relative bargain (he also comes with a team option/buyout situation for 2028).

Stanton’s also moved back to the outfield far more often in 2022, allowing the Yankees to experiment with their Big Boy Lineup, which has helpfully awoken his bat and led the Bombers to the top of the American League.

Oh, and his last three postseason appearances, for all the Brian Kennys out there? .286 with two bombs against Cleveland in the 2020 WC round, .316 with four bombs and 10 RBI against Tampa Bay in the 2020 ALDS, and a 3-for-4 game against Boston at Fenway with what should’ve been a trio of homers, but was actually just a single blast. When he’s on a heater, he can hit any level of pitching.

Again, all in the timing.

9. David Price – 1 Year, $16 Million of Red Sox Money Remaining

We can’t reasonably place Price’s lingering single season of burden higher on this list, but we’d also be remiss if we went a whole 10-deep list without noting that the Boston Red Sox are still paying Price to maybe not even play for the Los Angeles Dodgers, who are also shopping the ex-ace to give him a better opportunity to start.

This one-year half remainder is of course the last vestige of the seven-year, $210 million deal Dave Dombrowski signed him to prior to the 2016 season. Necessary to bring the rotation boom back to Boston? Probably; Price underperformed (especially against the Yankees), but was ultimately a key piece on the 2018 World Series champions (frustratingly so).

His contract was tacked onto Mookie Betts in order to facilitate the lamest Sox blockbuster of their modern era of cost-cutting, leaving Boston with half of the lefty’s $32 million AAV for his age 34-36 seasons. Even though the 2020 pandemic saw Price’s salary pro-rated (he also opted out), that’s still a bucket of cash to pay a regressing lefty you don’t even employ anymore.

Thanks for the memories, David Price’s contract. We’ll miss you when you’re off the books.

More Articles About the Worst of the Yankees:

8. Jose Berrios – 7 Years, $131 Million Remaining

Berrios’ deal was signed just before the 2022 season opened, and so far, the returns have been largely questionable.

Yes, Toronto had to finalize a long-term pact to justify surrendering Austin Martin, one of their blue-chip infield prospects, at the 2021 deadline. But … 35 strikeouts in 47.1 innings with a 4.75 ERA in Year 1 of 7 does not an exceptional contract make.

Berrios ranks so far back on this list because he has so much runway left to reestablish himself and is still just 27 years old, meaning his entire high-dollar prime will be spent in Toronto with one of the game’s best offenses. But the early going has not been kind to the electric righty with the sweeping breaking ball.

And when you look to the Statcast metrics? Things get even bleaker.

In a season entirely comprised of a small sample size thus far, it’s highly possible to turn things around in the blink of an eye. Just look at what happened last week to Trevor Story (more on him in a bit).

As of May 24, though, Berrios ranks in the 12th percentile in average exit velocity, 15th percentile in hard-hit rate, 5th percentile in xWOBA, and so on and so on and SO blue. Nothing about his profile thus far is encouraging for predicting future performance.

And that future is locked in at six years following 2022 in Toronto “anchoring” the rotation in all the wrong ways.

7. Gerrit Cole – 7 Years, $252 Million Remaining

Cole’s contract is nice and clean: $36 million annually through his age-37 season. Simple. Pristine. You either get it or you don’t.

That hefty price point will always lend itself to wild fan base mood swings, but that’s not how we should evaluate the effectiveness of a long-term pact.

Of course the Bombers are running a risk here, but they didn’t tack on additional years to pay Cole into his 40s. Age 37 is unlikely to be the right-hander’s peak, but there’s also a good chance that one of the game’s elite arms doesn’t fall entirely off a cliff by that point.

And speaking of tack … call Cole “average” since MLB’s latest ban on foreign substances went into effect, but he’s largely displayed a similar level of dominance. Last August, he finished 3-0 with an 0.51 ERA and 24 whiffs in 17.2 innings before a balky hamstring struck him down for the remainder of the campaign. This season, he’s shaken off three difficult grind-it-out outings at the start of the season to go 4-1 with a 3.31 ERA and 62 Ks in 51.2 innings through his start on May 23 (another tough one that inflated the numbers a bit).

Cole’s deal is a risk the Yankees can afford to take, and there’s enough evidence on the table that he can persevere without adhesive. It was the sudden alteration to the baseballs last June that really got him (temporarily).

Will Cole still be elite without his Little Buddy in 2027? Unlikely, but possible. Regardless, his true talent level remains high enough that even four or five more great years will more than justify this inflated deal.

6. DJ LeMahieu – 5 Years, $75 Million Remaining

Why LeMahieu so low? The AAV is nothing compared to the other merchants on this list, and his overall multi-faceted offensive profile seems likely to age into at least decent performance for the remaining five seasons of his deal.

The Bombers stretched the 2019-20 MVP candidate’s deal an additional year to squash the annual financial burden, so his $15 million per year is nothing they can’t stomach.

Unfortunately, his deal has to make the list because of his 2021 regression. If 2021 LeMahieu is the starting point for his incoming performance, then perhaps committing to the player’s later years is a worse idea than we all thought.

Add in Gleyber Torres’ resurgence, a crowded infield, and several top prospects fighting their way to the surface over the next year or two, and LeMahieu starts to look like a versatile obstacle rather than a valuable hinge on a roster.

Unless he’s hitting. In that case, the team will always find room.

In 2021, LeMahieu hit the ball on the ground far too often, and posted a slightly-below-average 97 OPS+ while battling a sports hernia that seemed to debilitate him. So far this season, there’s been more lift and separation in LeMahieu’s swing, but in a depressed offensive environment, he’s only managed to be above-average (109 OPS+) rather than exceptional, the way he was in his first two seasons in New York.

If he continues walking down this path, or regresses, his contract will look more like an albatross, even at a moderate value.

4. Hyun-jin Ryu – 2 Years, $40 Million Remaining

If you’re the Toronto Blue Jays and you want to woo major stars, you need to start with a free agent overpay to really set the era in motion.

Left-hander Hyun-jin Ryu was Toronto’s choice in the 2019-2020 offseason, and the Jays secured his services for ages 33-36 coming off a second-place finish in the Cy Young chase.

Bizarrely enough, Ryu also finished top three in the Cy Young voting in 2020, a fact most surely forgot because of the raging pandemic that swallowed that entire shortened year whole. At this point, though, Toronto fans likely can’t shake the thought that Ryu wasted his last effective and healthy season in the bizarre Empty Season Baseball campaign played in Buffalo.

In 2021, Ryu took a step back, eating 169 innings but posting a 4.37 ERA, 4.02 FIP, and league-average 102 ERA+. By the second campaign of his four-year deal to front the rotation, the left-hander was already looking more like a mid-rotation option, a trend that has only worsened in 2022.

This season, Ryu has battled a forearm issue, striking out 11 in 18 innings while sporting a 6.00 ERA in four starts. His profile always baked in deception, and his dominance wasn’t reliant on upper-echelon stuff. Now, with two years still on the books, the Jays have their fingers crossed Ryu can hang onto … something.

They’re also probably pretty happy not to see Robbie Ray on this list, either.

3. Matt Barnes – 2 Years, $17 Million Remaining (Plus 2024 Option)

There are larger deals for longer periods of time on this list for sure. But nobody wants Matt Barnes, who has actively clogged up the back end of the Red Sox bullpen (and rotation, somewhat) with his ill-timed extension, making him both an essential member of the roster and a constant drag.

For whatever reason, spendthrift executive Chaim Bloom rewarded the erratic Barnes in the middle of his lone All-Star season, locking in his dominant closer for 2022 and 2023 (plus a buyout) … just before he started to regress again, pitching himself out of a bullpen role by October. That’s very difficult to do.

Barnes’ new deal came at his apex, and it’s hitting NOW, at his ultimate valley. You have to be as bad as Barnes for a short-term extension to hit a list like this. In 8.0 innings last July, Barnes finished seven games and posted a 1.13 ERA. In 6.2 August innings that followed the deal, he allowed 10 earned runs to the tune of a 13.50 mark with a 2.70 WHIP. In 2022, he’s already been worth -0.7 WAR, hoisting a 6.59 ERA up the flagpole in 16 appearances.

And, what’s worse, his struggles made secret weapon Garrett Whitlock essential in the bullpen … so when he moved to the rotation, the entire thing destabilized (including Whitlock, who’s been less than spotless in longer duty).

Barnes won’t be around forever, but he’s untradeable and uncuttable, thanks to Bloom’s master maneuver.

2. Chris Davis – Still Being Paid at Least $1.4 Million Annually Through 2037

At least.

When I was at the outset of this article, I mumbled out loud, “Damn, I … I wish I’d been able to write something like this back in 2019. Back when bad contracts were bad. Back when Chris Davis was masquerading as a major leaguer by playing three games per week, striking out 18 times somehow, and pining for the good old days, when he did the same exact thing but offset the pain by homering 53 times.”

Then I did a quick Google search and wept with joy. Not only is Davis’ mega-deal still on Baltimore’s books thanks to some Bobby Bonilla-esque magic, but it’s still on the books for another decade and a half.

Davis’ career hit its nadir in 2019, when he finished a hitless streak that spanned two seasons and reached 54 at-bats. Eventually, tensions boiled over so hard that Davis and manager Brandon Hyde had to be restrained in the dugout later during that frustrating-as-hell summer. After undergoing surgery prior to 2021, he finally announced his retirement, subtly also announcing that he’d be earning $9.167 million in 2023, 2024, and 2025, followed by $3.5 million annually from 2026-2032, followed by the aforementioned $1.4 million through the end of 2037.

A sad on-field ending for a former great without a doubt, but the fun in the bank account never ends.

1. Chris Sale – 3 Years, $85 Million Remaining

It makes total sense why the Red Sox paid Chris Sale after they won the 2018 World Series, rewarding him with a five-year, $145 million deal in March 2019 that was set to take effect in 2020. That’s a relative bargain for one of the game’s elite swing-and-miss artists, and also the Red Sox are the RED SOX.

Or, at least they were under Dave Dombrowski. Back then, men used to be men.

Sale, naturally, succumbed to the elbow injury most had long predicted for him based on his violent windup in the summer of 2019, ending that season — his worst in the bigs — with a 6-11 record and 4.40 ERA (despite 218 strikeouts in 147.1 innings).

When the 33-year-old Sale is at his best, he’s still nigh unhittable. Unfortunately, the 33-year-old Sale is currently on the IL yet again with a rib fracture, his timetable for return still unclear. The 33-year-old Sale is also 33 years old.

Since inking his mega-deal, the left-hander has rarely been available, and came back at the tail end of 2021 to provide a playoff boost … but often looked like an imitation of his best self instead. Boston worked Sale back into shape with “warmup” regular season outings against the Orioles and the AL’s dregs, but the Astros took him to the woodshed early in the ALCS, then edged past him in his second outing of the series.

We’re still waiting for a 2022 encore. If Sale looks excellent, he can opt out at the end of the campaign. If he doesn’t, he’ll still be on Boston’s books through 2024 — or 2025 at an additional $20 million if his option vests with a standout ’24 campaign.

5 biggest free agency and trade misses in modern Yankees history

The New York Yankees failed to sign or acquire these five players in recent years and it's really affected the trajectory of the franchise in a bad way.