Trade Retrospective: Yankees acquire Didi Gregorius in three-team trade with the Diamondbacks and Tigers

For the fifth straight offseason, BtBS is looking back on some of the biggest trades from years past. Check out all the entries here.

Early in December 2014, the Yankees executed a big three-team trade to fill their new vacancy at shortstop. They acquired Didi Gregorius from the Diamondbacks and sent Shane Greene to the Tigers. The Tigers sent Robbie Ray and Domingo Leyba to Arizona to complete the trade.

In this trade retrospective series, trades will be evaluated based on what was known at the time. That is the only fair, logical way to evaluate trades and strip luck out of the equation: process over results. Having said that, we will still take a look at how the trade worked out for both parties.

The Deal

After the 2014 season, the Yankees were dealing with two situations they had not had in over 20 years: missing the playoffs in consecutive seasons and not having Derek Jeter. The team had not missed out on the playoffs in consecutive seasons since their now unthinkable 12-season drought that they snapped in 1995 (not counting the strike-shortened 1994 season). That return to the playoffs happened to coincide with Jeter’s short debut.

While we can make jokes about how the Yankees had needed a shortstop during Jeter’s entire career, with his recent retirement they truly had a vacancy, and obviously nobody available could fill such big shoes. Acquiring Gregorius was about as well as a team could have done at the time. In terms of the talent they gave up, it was a return that was hard to beat.

Believe it or not, when Gregorius was a prospect he was once compared to Jeter. It was a silly comparison not just because nobody should ever compare a prospect to a Hall of Famer, but also because the two were very different players. Gregorius was an excellent defensive shortstop, probably two or even three grades better than Jeter’s best years. Of course, the gap between them offensively was probably even greater. Jeter spent most of his career as a 70-80 grade hitter, while Gregorius had a career line of .243/.313/.366 and an 84 wRC+ in 724 PA at the time of the trade.

Despite his lack of offense, Didi was still developing, and he had the potential to be a solid regular thanks to his defense if the bat came along a little more. Even if he did not hit that ceiling, it was still a great return for Shane Greene, who was coming off a deceptively good rookie season with a 3.78 ERA but a more telling 4.35 RA9 with modest peripherals. He was really no more than a back end starter.

The Diamondbacks were coming off a league-worst 64 wins, and they were going into the offseason with new GM Dave Stewart, who did not exactly have a successful stint in Arizona. It’s a shame he had to sell low on Gregorius, as getting zero top-100 prospects back in this trade was not a great return, but despite Didi’s upside, the fact of the matter is that he had been a disappointment so far in his career. Chris Owings was showing more promise, too. He was not hitting much, but his .311 wOBA in 2014 was 24 points higher than Didi’s.

This is not to knock Ray and Leyba, though. Ray had a disastrous short debut for the Tigers, but he was called up too soon. He had the potential to be a decent major league pitcher, but he needed further development to reach his upside. As for Leyba, he was a little more than a lottery ticket. He was a second baseman with some feel for hitting who could make lots of contact, but he lacked speed and power, so he would need to hit for a high average to be a regular.

The Tigers were coming off another disappointing postseason run having been swept by the Orioles in the ALDS, though it was their fourth consecutive year making the postseason and winning the division. Looking towards their starting rotation for 2015, it was great that they had David Price, whom they acquired at the trade deadline, but they were going to lose Max Scherzer in free agency, and though there was no replacing the future Hall of Famer, they needed somebody better than replacement level to fill that slot in the rotation. This was also before they traded away Rick Porcello for some outfield help.

Shane Greene was certainly not going to be a star, but he would very likely be a win or two better than whomever the Tigers would have trudged out there instead. Also, unlike Ray, he was ready now.

This was a great trade for the Yankees, a solid one for the Tigers, and a little less so for the Diamondbacks. One can certainly argue that it was a better trade for the Dbacks than what I’ve laid out here, but I believed in Didi’s upside at the time and would not have parted with him for this return. As it turns out, the Diamondbacks did just fine in this trade.

The Results

Gregorius had a very good first year with the Yankees. His bat was still light, hitting .265/.318/.370 for a 92 DRC+, but that is still worth 3.0 WAR from a slick fielding shortstop. The Yankees succeeded in snapping what was for them a big two-year playoff drought in 2015, but they lost to the Astros in the Coin Flip game.

Didi’s offense got better and better each year until it peaked in 2018. That year he hit .268/.335/.494 for a 121 DRC+, and he finished his second consecutive season with over 4.0 WAR.

Unfortunately, Gregorius needed Tommy John surgery and missed half of the 2019 season. When he came back, his offense regressed, which was really bad timing given that it was a contract year. He still hit for good power, perhaps because of the juiced ball, but his .276 OBP was brutal. The Yankees decided to part with him in free agency since Gleyber Torres could take over at shortstop. Gregorius ended up landing with the Phillies on a one-year, $14 million deal.

Greene’s first year in Detroit was nothing short of disastrous. He pitched in 18 games, 16 of which were starts, and had a ghastly 7.21 RA9. Peripherals don’t really matter when you are allowing so many runs, but his strikeout rate was at an awfully low 14.7 percent. The Tigers demoted him to the bullpen the following year.

The bullpen looked like the right place for Greene, as he had a 2.79 RA9 and 2.4 WAR in 2017, even though his control took a nose dive that year that now looks out of place with the rest of the year. He walked 12 percent of batters faced that year but less than seven percent each year after.

Greene’s career is one of peaks and valleys. Following his excellent 2017 season, he had a 5.54 RA9 in 2018 and then a 2.61 RA9 in 2019 before the Tigers sold high on him at the trade deadline. He regressed again with his new team, the Braves. If there actually ends up being a 2020 season, he will still be in Atlanta.

Outside of a great 2017 season, Ray has been little more than a solid back of the rotation pitcher. He has a career 4.30 RA9 with the Dbacks and interesting peripherals. He has had excellent strikeout rates in that time, having struck out about 31 percent of batters faced, but he has also walked about 11 percent of them.

Lebya just made his major league debut in 2019, and it was a solid one, albeit in only 21 games and 30 PA. He hit .280/.367/.440, though he did not show anything close to the contact rates he showed in the minors, but again, it is a minuscule sample size. The Diamondbacks did well with 85 wins in 2019, so if Lebya can make the leap, it might be enough to squeeze the team into a Wild Card slot.

That’s excellent considering the Yankees got that for just Shane Greene. Even if Gregorius landed in the nine or ten-win range this would have been a win for the Bronx Bombers.

That’s really disappointing, and it looks a lot worse after seeing how good Gregorius was in New York. Considering that the Tigers have entered a rebuild since the trade, they might have been better off hanging on to Ray and Leyba. They could have traded Ray in, say, 2017 for a better return, and hung onto Leyba for their next competitive team.

Unlike just about every table I have ever done for this series, this one is very much in progress. Ray still has one year left in Arizona before free agency, and Leyba is just getting started. However, it is somewhat offset by Owings, who took over for Gregorius at short. From 2015-2018, he hit only .246/.287/.372, a 69 wRC+, and combined for only 1.6 WAR.

As I said before, I was a little low on the return for the Diamondbacks. Yet they could very well end up “winning” this trade, and that is saying a lot considering how well Gregorius worked out for the Yankees.