Ranking Brian Cashman's worst pitching trades for Yankees

We had some time to cool off after the Frankie Montas shoulder surgery news, which marks another sunk cost in a long line of them for the New York Yankees. The right-hander will likely finish his time in the Bronx making just eight starts over a year and a half after an injury that was well-documented prior to the trade at least year's deadline ended up hindering him in 2022 and knocking him out for most (if not all) of 2023.

Unfortunately, this has become an all-too-familiar narrative for the Yankees under general manager Brian Cashman, who has continued to whiff on most trades concerning pitchers (chiefly starters). Loyal fans will point to his acquisitions of Luis Cessa and Chad Green back in 2016, Tommy Kahnle and Michael King back 2017, and more recently guys like Clay Holmes, Wandy Peralta and Lou Trivino ... but that's not enough to win a World Series. It's a good start, but that's about it.

Had two of these gone the Yankees' way, we're singing a completely different tune. But the vast majority of the misses have been catastrophic, and we'll relive the pain after Montas' injury sent the Yankees from "best rotation in baseball" to "we have no idea who the fifth starter will be for all of 2023." Fun times.

Ranking Brian Cashman's worst pitching trades for the New York Yankees

2015: Aroldis Chapman

It sure does seem harsh to put Aroldis Chapman on this list because he finished his Yankees career with a 2.94 ERA, 2.89 FIP, 1.15 WHIP, 453 strikeouts and 153 saves across 315 games (294.1 innings). BUT ... the Yankees traded for him under shady circumstances (he was under investigation for domestic violence), directly played a part in ruining three postseason runs (2017, 2019, 2020), and was signed to an unforgivable contract extension after blowing the 2019 ALCS.

Had the Yankees let Chapman depart after 2019 following an opt out, Yankees fans probably have no ill will. But those extra three years and $48 million left everyone with a sour taste in their mouths, especially with how he performed in 2022 (prior to ditching the team for the postseason because he wasn't guaranteed an ALDS roster spot).

And by the way ... who gets a tattoo infection in the middle of a division race?

2010: Mark Melancon

Yes, Mark Melancon was a Yankee! The Yankees drafted him in 2006 and then traded him to the Houston Astros (alongside Jimmy Paredes) in the Lance Berkman deal in 2010. This one's different because it's Cashman trading a pitcher away, but the point still stands! He seemingly can't do this! So how did that one turn out?

Melancon immediately delivered for the Astros (classsssic) by going 10-4 with a 2.85 ERA, 3.24 FIP, 1.21 WHIP, 85 strikeouts and 20 saves across 91.1 innings between 2010 and 2011. A brief and horrible layover in Boston in 2012 took him off course for a moment, but then he found his stroke in 2013.

He spent four years with the Pittsburgh Pirates and earned three All-Star nods and racked up 130 saves, all the while maintaining a 1.80 ERA and 0.93 WHIP. He fell off a bit when he left the Pirates. From 2017-2019, he spent time with the Giants and Braves, but couldn't maintain his dominance. Then, in the shortened 2020, he got back on track with Atlanta before leading the league in saves with the Padres in 2021. He came crashing back down to earth with Arizona in 2022, but the Yankees could've had a lengthy, successful career from a back end reliever instead of 37 games of Berkman, who suffered an ankle injury after the acquisition and also injured Alex Rodriguez by rocketing a line drive off his ankle. Epic.

2016: Andrew Miller

Another trade-away! Let's keep these rolling. The Yankees missed the playoffs in 2016 and were nothing to write home about, but they had a monster bullpen that featured Chapman, Dellin Betances and Andrew Miller. In fact, the four-year, $36 million contract given to Miller after the 2014 season might've been Cashman's best work!

But then came the trade deadline, and the Yankees determined they would be sellers (smart move). Chapman was sent to the Cubs in a deal that included Gleyber Torres, and Miller was sent to Cleveland (who met Chicago in the World Series that year!) for a package of Justus Sheffield, Clint (Jackson) Frazier, Ben Heller and JP Feyereisen. Guess how many of those guys from the Miller deal are with the organization today? None!

In fact, Sheffield reportedly prevented the Yankees from acquiring Manny Machado (because Cashman didn't want to get rid of him, but was fine trading him for another pitcher on this list!). Frazier's time in the Bronx was mired in controversy and disappointment. Heller was nothing more than bullpen filler. Feyereisen was traded again and then got good with the Rays (he's a Dodger now).

Miller would've REALLY helped on the 2017 Yankees, huh? When they couldn't score runs against the Astros and needed the pitching staff to be nails? Oh, what do you know, he was an All-Star in 2017 with Cleveland and finished with a 1.44 ERA, 1.99 FIP and 0.83 WHIP. It wasn't until 2018 that his career went off the rails.

But, yeah, 2017 could've been that much more special had Miller been in pinstripes.

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2012: Michael Pineda

Big Mike! What do you remember him more for? His incredible 13-start stretch in 2014 ... or when he was ejected during a game against the Boston Red Sox that same year for using pine tar?

Gotta be the latter, right?! All in all, this was a big "nothing" trade. The Yankees sent catcher Jesus Montero and pitcher Hector Noesi to the Seattle Mariners for Pineda and pitcher Jose Campos. But far too much trust was placed in Pineda to deliver, which was the ultimate problem here.

In the end, injuries and lackluster play characterized Pineda's stint with the team from 2014-2017 (31-31, 4.16 ERA and 1.22 WHIP in 89 starts). And then, in classic Yankees fashion, Pineda left, went to the Minnesota Twins, and somehow finished 22-13 with a 3.80 ERA and 1.19 WHIP in 53 starts there from 2019-2021. Every time they leave, they perform better. You can't make it up.

Pineda was unable to separate himself from a wack pack that consisted of an aging CC Sabathia, Ivan Nova, Nathan Eovaldi and eventually He Who Must Not Be Named. It was a weak crew, and Pineda was weaker or just as weak.

2017: Jaime Garcia

How about blowing the lid off that 2017 playoff race?! After the big trade with the White Sox that brought Todd Frazier, Tommy Kahnle and David Robertson to the Bronx, Cashman followed that up with ... Jaime Garcia? I'm sorry, I think I took too big of a hit. Who was it again?

Nope, guess the hit wasn't strong enough, because I did NOT want to hear Jaime Garcia, who thankfully was traded for nothing (Dietrich Enns and Zack Littell), but went 0-3 with a 4.82 ERA and 1.63 WHIP in eight starts. He had a couple of decent outings in there, but again, this is far from a championship trade, and that's how we'll have to view it.

The Yankees badly needed starting pitching in 2017 with Pineda going down for the year in early July, Sabathia running on fumes, and two young arms in Luis Severino and Jordan Montgomery finally getting their beaks wet. Garcia was clearly not the move to supplement the pitching staff for a playoff run.

The left-hander was out of MLB after a terrible 2018 with the Blue Jays and Cubs, too. Cool.

2018: James Paxton

Everybody wishes the James Paxton trade worked out. It was exciting at the time, and he possessed a top-of-the-rotation profile the Yankees desperately needed alongside Severino and Masahiro Tanaka. The only problem? He could never stay healthy ... something Cashman knew and still decided to roll the dice on.

We'll forever remember Paxton for buzzsawing the Red Sox in that incredible 2019 outing at Yankee Stadium, as well as his ALCS showing against the Astros (8.1 innings, 2 ER, 12 K) ... but injuries limited him in 2019 (only 150.2 innings pitched) and he eventually succumbed to Tommy John surgery in 2020 (only five starts and a 6.64 ERA). He's now a member of the Red Sox, but has yet to pitch due to more injuries.

Anyway, at the time of the trade, Paxton had never made more than 28 starts in a single season. In fact, he only had three years where he made 20 or more. And guess who was in this deal going back to Seattle?! Justus Sheffield, who the Yankees wouldn't trade the year prior for Machado! One of the other prospects? Erik Swanson, who's now a member of the Blue Jays after they bought high on the right-hander following a 1.68 ERA, 1.84 FIP and 0.91 WHIP year in 2022. That should work out well for New York, right?

Paxton came with high expectations and left with a whimper. It really was a shame he couldn't stay healthy at any point in his career, but the Yankees ignoring that important tidbit has this deal higher up on the list than it should be.

2018: JA Happ

Ohhh MAN! Another extenuating circumstance! Why? Because the trade for Happ actually wasn't bad. The Yankees traded Brandon Drury and Billy McKinney to Toronto in exchange for the left-hander, who went 7-0 with a 2.69 ERA and 1.05 WHIP in 11 starts down the stretch of the 2018 season.

But then came another extension nobody needed. Of course Happ was going to command cash above his actual value after that torrid run and the Yankees took the bait, signing him to a two-year, $34 million contract with a vesting option for a third year. Let's recall how that all unfolded.

Happ finished with a 4.91 ERA, 5.22 FIP and 1.30 WHIP in 31 games (30 starts in 2019). He was the king of surrendering first-inning home runs. More times than not, the Yankees found themselves in a hole when he took the mound. And then came the shortened 2020, which forced the Yankees to dance around his vesting option benchmarks so they wouldn't have to pay him an additional $14 million in 2021. It was an awkward situation nobody wanted.

But here's the grand finale. In Game 2 of the ALDS against the Rays, a series the Yankees led 1-0, New York opted to start Deivi Garcia, who was a pleasant surprise as a rookie that year when the rotation badly needed support. Garcia pitched one inning and the Yankees tried to pull a fast one on the inventors of "pulling a fast one." They used Garcia as an "opener" and planned for Happ, already disgrunted about his contract and very much NOT open to coming out of the bullpen, to piggyback the young right-hander. Happ got destroyed, allowing four earned runs on five hits and three walks in just 2.2 innings of work. The Yankees lost the game, 7-5, and eventually the series. That was the moment it all came crashing down, and every fan with a pulse knew it.

Trade = good. Judgement after the trade = never been worse.

2018: Lance Lynn

Why isn't Lance Lynn still on this team? Back in 2018, the right-hander was acquired from the Twins for Tyler Austin and Luis Rijo. Steal! Except he wasn't that impressive in his 11 games (nine starts). He finished with a 4.14 ERA and 1.33 WHIP ... but somehow had a 2.17 FIP. And nobody in this analytically-driven front office did anything with that information?

Instead, Lynn, who was bumped from the rotation to the bullpen against his wishes (we're spotting a trend, here!) left for the Texas Rangers in free agency. He finished fifth in the AL Cy Young voting in 2019 and then sixth in the shortened 2020 before being traded to the Chicago White Sox. In 2021, He earned his second career All-Star nod and finished third in the Cy Young voting. He experienced a bit of a backslide in 2022 due to a knee issue, but he was still better than anything the Yankees could've offered in the No. 4 or 5 rotation spots.

Here we have another instance where the trade was good and the decisions executed every moment following the trade were beyond poor. Since the start of 2019, Lynn has made ~$38 million. He'll make $18.5 million in 2023 and has a club option for 2024. Sub out any of Josh Donaldson, Aaron Hicks and/or Domingo Germán and you have a better team spending less money.

Technically not a "loss" on the trade, but we're still beyond bitter.

2021: Andrew Heaney

When's the movie about the 2021 Yankees coming out? Because it'll win an Oscar for Best Gut-Wrenching Drama That Was the Biggest Waste of Your Life. Is that a category at the Academy Awards yet? If not, Hal Steinbrenner should start looking at the accolades for indie festivals.

The trade for Andrew Heaney epitomized how depressing this season actually was. At the trade deadline buzzer, once again, Cashman sucked all the wind of the team's sails by trading for Heaney, who was ... never good! Showed signs of that possibly being the case a few times in short spurts, but nothing beyond that. But after 18 starts, a 5.27 ERA and 1.31 WHIP, the folks in the front office kicked back in their chairs, put their feet up on the desk, and said "you know what? THIS is the move that will reinvigorate this lifeless team and get them on track for a playoff run!"

Heaney's 12 games in New York might've been the worst of anybody from an output standpoint during the second half of the season. He finished with a 7.32 ERA, 6.93 FIP and 1.35 WHIP. He allowed an impossible 13 home runs in 35.2 innings of work. He was moved to the bullpen despite the fact he wasn't comfortable pitching in relief. Whatever the Yankees thought they could unlock, they somehow found themselves drowning in the opposite direction -- they made Heaney worse! How?!

ONE game was the difference between the Yankees or Red Sox hosting the AL Wild Card Game. The Yankees lost eight of the 12 games Heaney appeared in. Not saying they were all his fault, but those are the stats! A nightmare to watch, and it ended fittingly when the Yanks got embarrassed at Fenway that October.

Did we mention he left and got better, though? Can't forget about that inevitable occurrence.

2017: Sonny Gray

Maybe stop trading with the Oakland A's, Brian? Please? Even though Sonny Gray didn't cost much in that 2017 deadline deal ... and even though he pitched five very good innings of one-run ball against the Astros in the ALCS ... this couldn't have been advertised any worse as a failure.

The Yankees needed rotation reinforcements in 2017, but Gray performed more like a back-end starter than a frontline one. He started 11 games, the Yankees lost seven of them. But that was hardly the worst part. Yes, always remember, the story always gets worse when we're talking about stuff like this.

In 2018, Gray couldn't even finish the year in the rotation. And he wasn't used at all in the playoffs. In 30 games (23 starts), the right-hander went 11-9 with a 4.90 ERA, 4.17 FIP and 1.50 WHIP. Aaron Boone's first year on the job. What a joy. He moved Gray to the bullpen in August, which actually improved his 5.56 ERA.

On Aug. 1 of that year, Gray was booed off the mound after allowing seven earned runs on eight hits and two walks in a 7-5 loss against the 47-115 Baltimore Orioles. Gray was smiling as the boos rained down, and that was all she wrote for any support he had among the fanbase.

He was traded to the Cincinnati Reds in the offseason, where he went 23-20 with a 3.49 ERA, 3.57 FIP and 1.15 WHIP in 68 starts. Then he was traded to the Twins before the 2022 season and went 8-5 with a 3.08 ERA, 3.40 FIP and 1.13 WHIP in 24 starts. Always better once they leave.

2022: Frankie Montas

And it just keeps getting worse. Anybody gonna get a clue here? Though the jury's still out on the package that went to Oakland in exchange for Montas, the fact the Yankees are going to end up paying him ~$10 million for eight starts is the oversight of all oversights.

Montas, who dealt with a shoulder injury in July of last year (the same one that plagued him down the stretch and eventually needed surgery), was the 2022 deadline's consolation prize behind Luis Castillo. That's how big the gap was.

When the Yankees couldn't get Castillo because of the Mariners' insane overbid, Cashman went for Montas. OK! Sure. Rotation help is great, especially when you can't trust Severino to stay healthy and will have to manage Nestor Cortes' innings as the year progresses.

But wait, that's Brian Cashman's music! The hell is he doin' here?! Cashman, after acquiring Montas to seemingly bolster the rotation to the "next level," went ahead and traded Jordan Montgomery to the St. Louis Cardinals for an injured Harrison Bader, who couldn't suit up until mid-September. Hey, that trade might end up working out, but Cashman's dealings at the deadline completely killed morale and led to the Yankees' horrific slump that nearly saw them choke away a 15-game lead in the division.

As for Montas, he could've have been further from a viable replacement for even Monty! A 6.35 ERA and 1.54 WHIP in eight starts and a meaningless ALCS appearance (one run in one inning) vs Montgomery's 3.11 ERA and 1.08 WHIP in 11 starts with the Cards.

Cashman downgraded and thinned the rotation, acquired an injured player, and will now pay $7.5 million for him to not play in 2023, further derailing the team's pitching plans for this upcoming season.

Really not sure it gets worse than that.