Grading the Yankees' Trade for Jameson Taillon

In trading for Jameson Taillon, the Yankees upgraded their starting rotation. But there is some risk to the deal.

Needing to add another starting pitcher despite their limited luxury-tax space, the Yankees traded with the Pirates for right-hander Jameson Taillon. In return, New York sent four prospects to Pittsburgh. Let's grade the trade.

The Deal

Yankees acquire: RHP Jameson Taillon

Pirates acquire: RHP Miguel Yajure, RHP Roansy Contreras, INF Maikol Escotto and OF Canaan Smith

Grading New York's Side of the Deal

The Yankees added to their already volatile starting rotation with another high-upside pitcher coming off a serious injury. Taillon did not pitch in 2020 while recovering from his second Tommy John surgery. Injuries and testicular-cancer surgery at times have stalled his progress throughout his career, but Taillon, 29, is still young and talented enough to make good on his front-end starter potential.

How exciting a prospect was Taillon? The Pirates selected him second overall in the 2010 MLB draft, between two of the game's biggest stars, Bryce Harper (No. 1) and Manny Machado (No. 3). He had two serious injuries in the minors—his first Tommy John surgery (2014) and hernia surgery ('15)—before making his MLB debut in '16, when he made 18 starts and posted a 3.38 ERA and 7.4 strikeouts per nine. That July, he was hit in the head with a 105-mph line drive but, perhaps unwisely, was allowed to remain in the game.

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He started strong in 2017 before he underwent surgery in early may to remove a mass on his one of his testicles. At the time, he wrote on Twitter, “Today I lost a piece of my ‘manhood.’ But, today I’m feeling more like a man than I ever have.” Five weeks later, he returned to the mound. In '19, he took another line drive off his head.

Still, Taillon has been excellent whenever he's pitched without interruption. In 2018, he went 14–10 with a 3.20 ERA with 8.4 K/9 across 32 starts, including two complete games (one shutout). He made seven starts in '19 before again injuring his arm and needing his second Tommy John surgery. His then-teammate, right-hander Trevor Williams, said at the time, "We’re penciling him in for Comeback Player of the Year, 2021." That could be a smart prediction—in the American League.

Actually, the Yankees have at least two Comeback candidates in their rotation. Less than two weeks ago, they signed two-time Cy Young winner Corey Kluber, who was limited to just 36 2/3 innings over the past two seasons due to injuries. Luis Severino, their one-time ace, will begin the year on the injured list but is expected back sometime in 2021 after he underwent Tommy John surgery last February. Following the trade for Taillon, New York's opening-day rotation projects to look something like this: 

1. Gerrit Cole, RHP
2. Corey Kluber, RHP
3. Jameson Taillon, RHP
4. Jordan Montgomery, LHP
5. Deivi García, RHP/Domingo Germán, RHP

As I wrote last Thursday, after the shortest season in history, it's risky for the Yankees to rely on so many pitchers who are either young or returning from injury, or are both young and returning from injury. But, after trading for Taillon, the Yankees are perhaps better equipped than most to deal with these concerns. Besides García, their top prospect, the Yankees also have well-regarded righties Clarke Schmidt and Michael King who could fill a rotation spot if needed.

Recently, a scout who watched Taillon rehabbing from Tommy John surgery, told The Athletic's Lindsey Adler that Taillon "may be a #2 when it’s all said and done."

Taillon will make $2.25 million this year, and he won't be a free agent until after the 2022 season. That, and four good prospects, is an appropriate price to pay for a pitcher who, even after his second Tommy John surgery, could be one of the better starters in the league.

Grade: B+

Grading Pittsburgh's Side of the Deal

With their low payroll, previous last-place finishes and recent transactions, the Pirates are clearly in rebuild mode.

Already this offseason, they've traded slugger Josh Bell to the Nationals and right-hander Joe Musgrove to the Padres. It made sense they would also deal Taillon, with two years of club control left, before the season started.

For Musgrove, their top pitcher last year, the Pirates received a four-prospect package featuring, most notably, 19-year-old center fielder Hudson Head, their No. 6 prospect, per MLB.com. Considering Taillon is coming off his second Tommy John surgery, Pittsburgh made out fairly well with its return from the Yankees.

Miguel Yajure, 22, has four plus-pitches, with a good command and a fastball that tops out at 97. He should be ready to join Pittsburgh's rotation at some point this season. Roansy Contreras, 21, has three solid pitches, though his potential is more as a depth piece than a front- or mid-rotation starter. Canaan Smith, 21, is a powerful left-handed hitting corner outfielder, and infielder Maikol Escotto, 18, has impressive raw power, though he's a long ways away from the big leagues.

Grade: B