CC Sabathia has re-signed with the Yankees, but that doesn’t mean the front office’s work. Even though the roster already has five major league quality starters, the Yankees are still pursuing at least one more. Gerrit Cole is the most recently rumored name, though he’s not alone among potential trade targets. Given the organization’s prospect depth, it seems like some sort of deal from the farm’s surplus will be made in order to obtain a young starter.
Whether it’s Cole or another controllable starter like Michael Fulmer or Chris Archer, it won’t be general manager Brian Cashman’s first rodeo in acquiring a starter of that ilk. Cashman is unquestionably one of the sport’s best executives, and has pulled off a number of impeccable trades, such as the acquisitions of Nick Swisher and Didi Gregorius. Yet, if there’s a weaker aspect of Cashman’s track record, it’s his history of trades for starting pitchers with fewer than six years of service time (i.e. the free agency cutoff).
Since 1998, when Cashman took the helm, he’s made six trades for starting pitchers that still had future years of organizational control. Perhaps the process and decision making was sound in the midst of identifying and subsequently trading for this type of pitcher, but the results were not great for various reasons. Before diving into the trades made, I’d suggest not being overly critical of deals made more than a decade ago, as the degree of information available then pales in comparison to what front offices have nowadays.
Off we go:
Jeff Weaver
Oy vey. Jeff Weaver was the first controllable starter that Cashman acquired in his tenure. In July of 2002, the Yankees deal Ted Lilly, John-Ford Griffin, and Jason Arnold as part of a three-way trade with Oakland and Detroit in order to land Weaver from the Tigers.
| Player | Control through | Controlled WARP | Controlled ERA+ |
| Jeff Weaver | 2005 | 4.3* | 83 |
| Ted Lilly | 2006 | 16.4 | 103 |
*The Yankees traded Weaver after the 2003 season.
At the time, Weaver was an impressive workhorse for Detroit and was off to his best start yet in 2002, with 3.26 ERA and 3.38 DRA in 17 starts prior to the trade. He had also come off of two consecutive 200 inning seasons and was not yet 26 years-old. Infamously, Weaver’s career in the Bronx was short-lived despite the Yankees having his rights through 2005. His final and most notorious pitch with the Yankees was this. Did you close YouTube the second you realized what the video was? Me too, though I took a split-second to copy and paste the link. Ugh. Anyway, Weaver was sent away to the Dodgers in a deal that brought Kevin Brown to New York (oh, what a joy that deal was too).
Lilly, meanwhile, put together a solid resumé with Oakland and Toronto prior to becoming eligible for free agency. The southpaw was nothing spectacular, but certainly a fine back-end starter in the mid-aughts. Griffin and Arnold wound up being inconsequential pieces.
The verdict: this is a trade that I think most of us would like to forget. It wasn’t a backbreaker, as Lilly didn’t become star, but he would have been far more useful considering he essentially the type of pitcher that the Yankees were hoping to get in Weaver. Hindsight, as always, is 20/20 here. Lilly was only starting to figure things out in 2002, right before he got dealt, whereas Weaver did appear to be a useful arm for a couple of seasons prior to the exchange. Further, let’s keep in mind that this trade occurred 15 years ago, and the Yankees front office has obviously evolved since then.
Javier Vazquez
In the same winter that the Yankees dumped Weaver, the team made a big splash to acquire then 27 year-old Javier Vazquez from Montreal. Vazquez was only a year away from free agency, so he’s not exactly the best example of a trade for a controllable starter, but the Yankees did immediately sign him to a four-year extension after the deal. To add Vazquez, the Yankees dealt Nick Johnson, Juan Rivera, and Randy Choate.
| Player | Control through | Controlled WARP | Controlled ERA+/OPS+ |
| Javier Vazquez | 2004 | 4.4 | 92 |
| Nick Johnson | 2007 | 11.3 | 133 |
| Juan Rivera | 2008 | 7.2 | 109 |
It was a big haul for the Expos, but certainly commensurate for a pitcher of his caliber. Vazquez had already accumulated 30.5 WARP at that stage of his career, and was coming off a dominant campaign: a 3.24 ERA and 2.50 DRA in 230 2/3 innings pitched. Unfortunately, despite the contract extension, Vazquez lasted only one year in New York. His downfall was the long ball; he surrendered 33 homers in 198 innings in 2004. After the season, he’s was the centerpiece in the trade for Hall of Famer Randy Johnson.
Rivera had a nice career after the trade but wasn’t a big loss. Johnson, who was stuck behind Jason Giambi on the depth chart, was an excellent hitter for the Expos/Nationals when healthy. Both were well regarded in the Yankees’ system before the trade, particular Johnson, who was one of the game’s top prospects at the turn of the millennium.
It’s evident that Vazquez’s (first) stay in New York didn’t go well, but I’d argue that the bigger mistake was giving up on him after merely one season. This is a case where the process of identifying a young starter to acquire made plenty of sense, but the downfall was that the results didn’t come immediately. That said, it’s difficult to be certain whose idea it was to eschew Vazquez after one year, as it certainly seemed like a George Steinbrenner move to deal him for Randy Johnson. However, like the Weaver deal, there’s not much to relate to the current front office, as the Yankees certainly operate in a much different manner in 2017.
Shawn Chacon
I wasn’t sure if I should bother to include this one, but I figured for completeness that I should. Chacon was a trade deadline addition in 2005, and actually pitched quite well down the stretch (and in one ALDS game). Granted, his 5.74 DRA in the Bronx in 2005 doesn’t support his sparkling 2.85 ERA, but in that instance, it was better to be lucky than good.
The Yankees acquired his rights through the 2007 season, but dumped him before that (hello, regression). He had a 7.00 ERA and 8.90 DRA in 63 innings in 2006 before being unloaded to the Pirates.
The return for Chacon was minimal: minor leaguers Eduardo Sierra and Ramon Ramirez. Sierra never made the majors, while Ramirez bounced around while having a couple of decent seasons early in his career. Not a big loss, though.
I wouldn’t put any stock in this trade when judging Cashman’s history for controllable pitchers. Chacon was essentially a flyer, not a big bet to be a mainstay for years to come. Further, this deal is more than a decade old.
Michael Pineda
On to the more recent and relevant moves. Cashman went nearly seven years before making another swap for a young starting pitcher. The wait sure resulted in a doozy of a deal prior to the 2012 season. The Yankees got Pineda, one of 2011’s top rookies (3.74 ERA, 3.03 DRA, 4.3 WARP) in exchange for Montero, who entered 2012 as the game’s seventh-best prospect.
| Player | Control through | Controlled WARP | Controlled ERA+/OPS+ |
| Michael Pineda | 2017 | 9.9 | 101 |
| Vicente Campos | N/A | -0.2 | 149* |
| Jesus Montero | 2017 | -2.6 | 88 |
| Hector Noesi | 2017 | -0.7 | 70 |
*Campos pitched only 5 2/3 innings with Arizona in 2015.
Pineda didn’t pitch for the Yankees until 2014 because of his shoulder and was mostly an enigma thereafter. He’d go through stretches of dominance and bouts of misery, and eventually succumbed to Tommy John surgery this summer just as he became eligible for free agency.
Montero, the other headliner, was an incredible bust for Seattle. The Yankees dodged a bullet there, though looking back, it’s easy to argue that his trade value could have been better utilized elsewhere. Hey, they tried with Cliff Lee. The other two pieces of the trade, Campos, and Noesi, didn’t move the needle much either way.
There’s no question that the Yankees got the better end of this deal, but it’s not like the front office obtained the value it expected. In that sense, the deal could be considered a failure, but was it the result of bad luck or a poor decision? One could argue that Pineda’s velocity decrease at the end of his rookie season was a harbinger of a shoulder injury to come. On the other hand, Pineda significantly underperformed his peripherals in New York, so perhaps there was a bit of misfortune. Either way, it’s safe to say that this deal fell short of expectations.
Nathan Eovaldi
Prior to 2015, Cashman traded for Nathan Eovaldi, the fireballing right-hander previously with the Marlins. Along with Eovaldi, the Marlins sent the Yankees Garrett Jones and Domingo German. In exchange, the Yankees shipped Martin Prado and David Phelps south.
| Player | Control through | Controlled WARP | Controlled ERA+/OPS+ |
| Nathan Eovaldi | 2017 | 2.9 | 94 |
| Garrett Jones | 2015 | -0.4 | 67 |
| Domingo German | 2023+ | 0.4 | 147* |
| Martin Prado | 2016 | 6.8 | 108 |
| David Phelps | 2018 | 3.1 | 112 |
*German has thrown only 14 1/3 innings.
Despite the blazing fastball, Eovaldi was never able to miss many bats, and consequently, didn’t find much success in New York. The hope was that the then 25-year-old had some projection, and with some work on his secondary pitches, things would improve. That never came to be, and ultimately, Eovaldi succumbed to Tommy John surgery in 2016 which cut short his career in pinstripes. He was non-tendered that winter, a year before being eligible for free agency.
On the flipside, Prado was quite the useful player in the seasons the Yankees traded away. Phelps never amounted to much as a starting pitcher but has proved to be a useful reliever.
The Yankees lost this trade, no ifs ands or buts. It’s not that dealing Prado and Phelps was a dreadful mistake, but rather, identifying Eovaldi as a guy with untapped potential. It’s easy to dream of a guy with his fastball blossoming, but that neither the Dodgers or Marlins could unlock it was disconcerting, in hindsight. The Yankees weren’t able to figure him out, either.
Sonny Gray
It’s way too soon to judge the Sonny Gray trade, as he was just added in July and the Yankees hold his rights through 2019. Nobody in the return for Gray (James Kaprielian, Jorge Mateo, and Dustin Fowler) has reached the majors yet for Oakland, either.
The Gray trade is reminiscent of the Vazquez deal, albeit Gray having more years to go post-trade under the Yankees wing (not considering the Vazquez extension). Both Gray and Vazquez had proved to be stellar pitchers already, and the Yankees bet on both to be staples in the future.
Moving forward
Whether it’s Cole, Archer, Fulmer, or someone else entirely, Cashman will be taking a risk. Top prospects like Clint Frazier could be on the move for any of those three, a decision that the front office certainly doesn’t take lightly. It’s easy to move a top prospect for a surefire star, like what the Red Sox did to acquire Chris Sale last offseason. However, it’s very rare that a controllable, ace-caliber starter is available in a trade.
Now, just because I named a bunch of trades that didn’t work out doesn’t mean that someone the Yankees acquire in the coming weeks will be a flop. None of this is predictive, but rather, an illustration of what hasn’t worked out in the past, and perhaps illuminating for future decisions to be made. Maybe they’ll be more cautious on upside plays, avoiding deals for pitchers like Eovaldi. Perhaps they won’t give up on young starters quickly, like they did with Vazquez (I think they’ve proven that already). Whatever lessons that the front office has learned will hopefully make the seventh time a charm.
Photo credit: Gregory J. Fisher / USA TODAY Sports