-- A negative career OPS+? Maybe that's typical for Ivy Leaguers to play for the Sox.
My first guess was a pitcher, but CS confirmed that the correct answer was for a hitter. (And my initial guess went to a school that isn't even part of the Ivy League!). My question is does "Sox" imply red, or could it be a member of the White Sox? I have a White Sox player who fits the description

-- He never played for the Sox, but does hold the distinction of, via a player to be named later deal, being traded away by an expansion team before they even selected him in the expansion draft.
Got this one (I think), but from what I can tell, he has no affiliation at all to the Sox.

--He was included by Ritter and Honig as one of their 100 best, even though his career outside of Boston doesn't seem to have justified that prediction.
So, when I read this one I thought it implied that after he left Boston, his career went downhill (e.g. Nomar, Vaughn). But nobody on the 100 list matched that description. Is this question worded trickily? i.e. is it implying that his away numbers were nowhere as good as his Fenway numbers? If so, I (obviously!) got this one too.

--One of the best control pitchers of modern times, he walked just 40 batters over two seasons and 446.2 innings!
For the record, this one has me REALLY stumped. I've gone to baseball reference and checked about 100 pitchers that I could think of, and still haven't found him. Question - what does modern times mean? I only looked form about 1960 onwards - do you mean modern as in after the 1800's??

The rest I think I got.

-- A negative career OPS+? Maybe that's typical for Ivy Leaguers to play for the Sox.
This question has TWO possible answers. The one you found is not the one Charles found. I learned this the hard way.

-- He never played for the Sox, but does hold the distinction of, via a player to be named later deal, being traded away by an expansion team before they even selected him in the expansion draft.
Got this one (I think), but from what I can tell, he has no affiliation at all to the Sox.
CORRECT

--He was included by Ritter and Honig as one of their 100 best, even though his career outside of Boston doesn't seem to have justified that prediction.
The career didnt go downhill as much as just not lead to the HoF and isnt really a top 100 by todays standards. Still a hell of a career.

--One of the best control pitchers of modern times, he walked just 40 batters over two seasons and 446.2 innings!
For the record, this one has me REALLY stumped. I've gone to baseball reference and checked about 100 pitchers that I could think of, and still haven't found him. Question - what does modern times mean? I only looked form about 1960 onwards - do you mean modern as in after the 1800's??
He pitched after 1960.

Are we talking last names only, or both first and last? LAST ONLY

Are the names supposed to remain in the same order as the clues are listed above? Or is this like the Soul Train Scramble, where we put the names in whatever order is necessary to give us the answer? YES, SAME ORDER AS ABOVE

Since the names have varying amounts of letters, is the diagonally-hidden message conveyed within all 10 names? In other words, is it a full 10 characters long? You start over at one point. Its pretty obvious when it happens.

Are we to assume this is like a word search, where the message can appear L to R, R to L, top to bottom, and/or bottom to top? Left to right, like with common english. If the answers were in hebrew, the secret message would appear right to left. Got it, gentile?

-- A negative career OPS+? Maybe that's typical for Ivy Leaguers to play for the Sox.
This question has TWO possible answers. The one you found is not the one Charles found. I learned this the hard way.

I didn't realize there were two - I should definitely edit this, then!

A negative career OPS+? Maybe that's typical for Ivy Leaguers to play for the Sox.
--> Chick Maynard (this is my 3rd guess. First guy was a pitcher, second one was a WHITE sox batter. I hope this one is right)

He never played for the Sox, but does hold the distinction of, via a player to be named later deal, being traded away by an expansion team before they even selected him in the expansion draft.
--> Scott Baker

This guy once had a 172-pitch, 10-walk outing, though it would have been shorter if he hadn't given up a 9th-inning homer.
--> Wakefield

Despite 53 steals in just 96 professional games, this recent 10th and 6th round pick won't be in the majors anytime soon.
--> Emeel Salem

He was included by Ritter and Honig as one of their 100 best, even though his career outside of Boston doesn't seem to have justified that prediction.
--> Luis Aparicio? At first I thought it was Jim Rice and the "career outside Boston" was a trick question referring to his stats away from Fenway.

This man hit the last homerun off a pitcher during the season in which that pitcher set the single-season record for homers allowed.
--> Daryl Boston

One of the best control pitchers of modern times, he walked just 40 batters over two seasons and 446.2 innings!
--> Bob Tewksbury.

A controversial late first-round pick, his showing through A ball might be a good start to proving his detractors wrong.
--> Casey Kelly??? I really have no idea on this one.

He appeared during at least the regular season for three World Series champions with three different franchises, including both the Sox and the Yanks.
--> Mike Lowell

He managed the Mets for 465 more games than he played for them at the tail end of his six-time all-star career.
--> Willie Randolph

The last names are:
MAYNARD
BAKER
WAKEFIELD
SALEM
APARICIO
BOSTON
TEWKSBURY
KELLY
LOWELL
RANDOLPH

which diagonally spells: MAKEIN TEWO??? Or if broken out further MAKE A BELWO???

Are any of the above answers wrong? Don't give me the right answers, just let me know which ones I need to rework.

Frank Whitman (Mike Remlinger, Craig Breslow, and Red Kellett also fit the description)
Dmitri Young
Tim Wakefield
Emeel Salem
Fred Lynn
Darryl Boston
Bob Tewksbury
Ben Revere
Herb Pennock (although Mike Lowell works, too)
Willie Randolph

The last names are:
MAYNARD
BAKER - wrong
WAKEFIELD
SALEM
APARICIO - wrong
BOSTON
TEWKSBURY
KELLY - wrong
LOWELL
RANDOLPH

Look at those you have correct and find the theme. Then the last 3 are easier.

Rice isn't from Massachusetts (at least per what it says under the avatar), so the common theme in their last names may not stick out so clearly.

Great puzzle by the way. Not sure how you came up with the idea but excellent.

towns in mass....

The key word in clue #5 is "prediction". In other words, the player was ranked by Ritter & Honig in a certain list BEFORE his career ended.

I had enough of it figured out to be pretty sure of what the answer is, but I got the same answer to #2 as dylanmarsh, which was throwing me off. dylanmarsh: If you go back and run down that same expansion draft list with Plantiers wart's post in mind, you'll find the right guy.

Also: to those who are struggling with the Ritter/Honig one, go to amazon or wiki and check the original publication date of their top 100 book. In that time context the answer will be glaringly obvious.

Ahh, ok.

Scott Winchester for Dmitri Young.

Mike Lowell for Herb Pennock.

And yeah, the obvious answer is that they're all towns or cities in Massachusetts. So do I win?

I immediately recognized most of these as towns in MA. (Yes - even up here in the frozen tundra, I knew that Boston was in Mass. And Salem, and Lowell (thanks to the Spinners). And I had heard there was a town named Wakefield, and the rest sounded like they could be names of towns). Anyhow, I immediately thought of Lynn, MA and Fred Lynn. But the version of the 100 list I saw was from 1988 and did not include his name. The other two answers just took some more time on baseball reference and I got them too.