One more comment: For those that think the Pomeranz trade represents some grand change in team philosophy, or contributed to staff departures, consider the following:
In 2013, Ben Cherington, worried about the health of his pitching rotation, traded for Jake Peavy. The Sox sent Jose Iglesias to Detroit, and Cleuluis Rondon, Frankie Montas, and JB Wendelken to the White Sox. We all know about Iglesias at the time. Rondon was a non-prospect in the low minors. Montas was a decent looking 20 year old pitcher for Greenville. Wendelken was a 20 year old reliever in single-A. The Sox also received 25 year old Brayan Villarreal, a career minor league pitcher who's career had appeared to be flaming out due to control issues.
Peavy helped the Sox win a World Series, and netted 2 B-level prospects the following year, one of whom, Heath Hembree, pitched in the pen for this year's Sox. Iglesias has been flashy fielder, but seems to be slipping lately in that department. His career OPS remains well below 0.700. Rondon never made the majors. Montas has looked decent in limited AAA action until he got hurt. Wendelken is in the A's system and has shown little in limited major league action. Villarreal is out of baseball.
In 2011, Theo Epstein acquired Erik Bedard and Josh Fields for 4 prospects. At the time, Fields was a 25 year old relief pitcher stuck in AA, and would eventually be claimed by Houston in the Rule 5 draft the following offseason. Rodriguez was a young starter in single-A, who had a K/9 of 13.4 for Greenville. Tim Federowicz, a former 8th round draft pick, was a catching prospect who had acquitted himself well in half a season in Portland (0.745 OPS). Stephen Fife, a former 3rd round draft pick, was a 24 year old starter who went 11-4 for Portland that year, but had control issues. Chih-Hsien Chiang, a former 2B, was tearing up Portland (1.050 OPS) as an outfielder.
Bedard was the definition of "meh" with the Sox, even more "meh" than Pomeranz. He was also a rental, unlike Pomeranz. Despite the serious pitching woes of the Sox at the time (Dice-K was in the minors, Buchholz was injured, and Lackey had no elbow left), the price was considered quite high for a rental.
The two prospect with the most impressive stats, Rodriguez and Chiang, never made the majors. Federowicz is a backup catcher with a career OPS of 0.538 (although he may win a ring this year). Fife has had 16 career major league starts and is now back in the minors for Epstein's Cubs. Josh Fields, the prospect the Sox got in return, has found a home as an anonymous middle reliever for the Houston Astros.
In 2007, Epstein was concerned that Papelbon, Okajima and the 41 year old Mike Timlin were in danger of being worn out by the end of the season. So the Sox traded 3 well regarded prospects for Eric Gagne. There were warning signs, as Gagne's K/9 numbers were way down from his career average. But he had acquitted himself reasonably well in Texas with a 2.16 ERA and 16 saves. Beltre was a 17 year old outfield in the rookie leagues. Kason Gabbard was a middling prospect who had slowly advanced up to the big club, but had pitched well in 7 starts for the Sox that season. 25 year old David Murphy was considered the prize, with 23 major league games under his belt already.
I'll pass on reliving the Gagne nightmare. Beltre's major league career consisted of 22 games. Gabbard would have 20 more major league starts after he left Boston. We all know that David Murphy become a decent everyday outfielder.
Not sure I would second guess any of these trades, even if the impact was mostly meh. As much as I hated Gagne, he at least took 18 innings away from the other relievers.