Suffice to say, Gregg has not had significant success. That may change in SL 2014. The biggest reason for optimism for this observer is Miguel Cabrera. Cabrera was taken in the same spot the previous draft and won our MVP. I feel his offensive is stronger, and with the thought abounding that SL 2014 will likely be a lower scoring league than the previous year, that bodes well for Gregg's success.
Cabrera has speed and defensive flaws, though. Gregg has a generally fast team with Segura's and Pence's and Justin Upton's and Carlos Gomez's and the like on his roster. Bench baserunners include Span and Andrus, even Zimmerman, who are all fair enough as runners. His slower guys like Cabrera and Ortiz and Molina, and while not slow Pedrioa isn't a fast 2Bman, they can all steal with good success.
Molina and Gomez and Pedroia and Upton and Gonzalez and Segura are all top flight defensive players to boot, and even Gregg's backups like AJ Ellis and Span and Loney are strong defensively. So while those like Cabrera are not perfect, the total number of basestealers and fast runners and strong defensive players is high.
Beyond Cabrera offensively, I have heard that Gregg will struggle to score runs. Molina is a top notch catcher because he's a decent hitter and great defensive player, not great at both. The same goes for Gomez as a CF, decent enough hitter and great defensively is why he went 20th in the draft. Pedroia is decent enough offensively. Pence and Upton aren't great, but they are not terrible. Segura, like a lot of the SS's available, has offensive flaws. Gonzalez isn't that strong offensively. What Gregg has is several guys who are not great offensively, so he will rely on players like Gennett to be strong off the bench, on his basestealing to provide runs, on Ortiz to hit an above expected number of HRs, on someone like an Upton or Pedroia or Gonzalez or Moline to exceed projected offensive numbers. But most or all, Gregg's offensive success, again in what shapes out to be a down offensive SL, will rely on the best offensive player in the league in Miguel Cabrera putting up outstanding offensive numbers.
The ability to score runs is key to a balanced team, and pure offense and basestealing are plusses on Gregg's side. The ability for a defense to not make errors, and to not allow basestealing, and to hold (or peg) runners with strong OF arms, and these are all things Gregg valued in his draft, and these all contribute to a team's balance. What remains is pitching, which often separates contenders from the rest.
Gregg drafted 15Z Iwakuma, 13ZZ Wainwright, 13Z Zimmermann, 13 Miller and 13W Masterson as his rotation. Jim may have a better rotation, or Matt may have a better rotation, or if Matt Moore pitches more like a 16 than a W, I may have a better rotation. But Gregg's starting staff is without question among the better rotations in the SL.
How much or how smartly a rotation can be used and made a plus is often dependent on the supporting relief staff. Some would even suggest that a staff like Graham-Steve's is best because they will rely not on the relief staff to support the starters, but more than most the relief corps will be the stars, and it's the group as a whole that will end up shining. Gregg's biggest challenge may be his relief staff, in that they have some holes. The pitchers above a 17 are only Nathan and Hochevar. His lone lefty is 15 Paco Rodriquez. He does not have a high number of innings available, compared to a Greg or a Graham-Steve. But while the parts are not off the charts for his relief staff, this doesn't speak to me as a **bad** support staff for a top flight rotation. Nathan and Hochever are strong enough as a top two that I can envision success. O'Day and Jim Johnson can be successful. Balfour and Rodriguez can be successful also. On the whole, relief isn't Gregg's biggest strength, but it doesn't appear like it will unhinge what has the shape of a successful staff.
There is a reason that Gregg's team is in the Division of Death this season, and one of the big reasons, moreso than in any other season, is that the division includes Gregg and his well-balanced team.