2015 FA Ace?...

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Oh yeah. Because that's totally how it works with young pitching. Just ask the Royals.

I'm a Scherzer fan, but I wonder if he ever leaves Detroit if he keeps pitching the way he does and Mike Ilitch keeps being alive.

Bailey is intriguing because he's significantly younger than the others on this list. The NL-to-AL transition is a concern though.

Shields has durability and consistency going for him and we know he can pitch to top-end lineups in the AL East, but the age worries me. Might be interesting if you can sign him to a Roy Halladay contract.

Masterson... ask me in a year. He looked to be in decline coming into the season, had what seems like a fairly significant breakout, but his velo has been down significantly (?) recently. I don't know what he is, frankly.

Lester is basically an innings eater at this point. If the Sox can sign him for innings-eater money, fine. If someone wants to give him a contract because he still has some of that "ace" pixie dust on him, forget it. Of course if he pitches better next year this all changes, but at this point we're looking at 383.2 innings of average-to-slightly-below-average pitching from him since the start of 2012, so I'm betting on more of that going forward.

As with all free agent discussions, it's not just who you want the most, it's who you can get for what price. And as with all pitching discussions, it's a question of what happens over the next ~230 innings. Right now I'd say Bailey is the guy who's most likely worth breaking the bank for, but I'm probably also going to be wrong about that.

Obviously you can find examples both ways, but in the aggregate, young pitchers are a very risky proposition. In any case, the point of the thread is to discuss upcoming FA starters. Yeah, it's possible the Sox won't actually need any, but how about we just assume they will for the sake of the discussion?

I'd love to see the Sox do a Sabathia-esque contract with Bailey -- ie, one with an opt-out after three years -- but don't make the mistake that the Yankees did in not actually letting the guy walk after the three years.

I think its a player opt-out. If he succeeds enough to opt out, its well and good but the alternative could suck for Sox.

Well, the Red Sox since 2003 have had a convenient 10 starting pitching prospects who were team top 10 prospects after getting to at least AA the previous season. Continuing the theme that we're not like other clubs, the results indicate that folks are probably being a tad pessimistic about what we can expect from the current crop.

The yield (note that the percentages pitched at a season's primary level have been adjusted for MLB cups of coffees, i.e., they're based on average level pitched at):

One elite ace, for a while. Jon Lester, #2 prospect for 2006 after pitching the whole year in AA, made his rotation debut that year as a #2/#3 quality guy and, after losing most of a year, from 2008-10 averaged 5.9 WAR; the threshold for a #1 starter is 4.7 (per 33 starts).

One elite ace when healthy. Clay Buchholz, #1 for 2007 after splitting between AA and AAA (56%) with a memorable MLB taste, established as a starter in 2009, has a 5.6 WAR season and 3.8 this year in 12 starts.

One top #2 who may be turning back into an ace. Anibal Sanchez, Marlins' #3 for 2006 after the Beckett trade, after splitting between A+ and AA (64%), jumped to MLB that year and had 3.7 in half a season; after battling injuries, settled in as a #2 starter (3.3 is the threshold) and, after a #3-level season last year, has 5.0 already this year.

One inconsistent #2 / #3. Justin Masterson, #4 for 2008 after splitting between high-A (62%) and AA, debuted that year, became a starter the next, and has had 4.1 and a 3.3 in progress sandwiched around an 0.3.

One late-blooming #2. Jorge De La Rosa, #9 in 2003 after A+ (87%) / AA and #10 for the Diamondbacks after AA (81%) / AAA, became a starter in 2006 but only recently became a good one; on his way to a c. 4.0 WAR season a few years ago, got hurt, and has come back to have 4.1 so far this year.

One young, presumably improving #3 / #4. Felix Doubront, #5 for 2011 after AA / AAA (83%) with some MLB, had an off year and fell to 17, but became a starter in 2012 and has 1.9 WAR this year (#3 threshold is 2.3).

One elite closer. Jonathan Papelbon, #3 for 2006 after AA / AAA (64%) / MLB.

One top setup man. Junichi Tazawa, #6 for 2010 after AA (64%) / AAA / MLB. Hurt, became bullpen mainstay in 2012.

One possible back of bullpen guy. Michael Bowden, #7 for 2007 after A+ / AA (68%) and #2 for 2008 after AA (66%) / AAA plus MLB taste. Had a good year for the Cubs last year, 0.0 WAR this year.

One washout. Abe Alvarez, #10 for 2005 after AA (93%) / MLB.

The other lesson besides the high rate of return is the extremely variable length of maturation. Years between reaching AA with a subsequent top 10 prospect rating, and being established as a quality MLB starter:

1 Sanchez (from an A+/AA season); #1+, #4 (hurt), #5 (hurt), #2 x 3, #3, #1
1 Lester (from AA); #2/3, #3 w/illness, #1+, #1+, #1, #2, #5, #3
2 Buchholz (from AA/AAA); #2, #1+, #2 w/injury, #5 recovering, #1+ with injury
3 Doubront (from AA/AAA); #3/4; 5th starter the previous year
4 Masterson (from A+/AA); after 3 years as swingman / 5th starter, #2, #5, #2/3
6 J. De La Rosa (from AA/AAA)

Next year:

R. De La Rosa will be 4 years from A (64%) / AA (and not actually a prospect)
Webster will be 3 years from A+ / AA (63%), 2 years from AA, and coming off AAA (80%) / MLB
Workman will be coming off AA /AAA (76%) [/ MLB]
Ranuado (79%) and Barnes (96%) will be coming off AA / AAA
Owens will be coming off A+ (78%) /AA

Umm ... that's what's technically called a "fact." They've been massively better. The odds of this being random are remote, and may well have something to do with emphasizing makeup in drafting and signing, and in the quality of ml instruction.

Whether all that is predictive for this crop of prospects is a different question.

I get this but it's really not their choice, it's Kershaw's and his agent. I still think they re-sign him, but a guy with that talent at 27 years old!? He may just want to test the waters (or put another way, "Let's see if I can get the Dodgers, Yankees, Phillies and (insert team name(s) here) to get into a bidding war..."

I think it's plausible that one of Owens/Barnes/RDLR/Webster/Ranaudo pushes the parameters of their ceilings and becomes an ace. However I don't think it's very likely, at all.

We'd probably have a better chance with packaging a few of those guys up with other prospects for an ace.

Teams seem to be jumping on the bandwagon of locking up young elite pitching, but if a Kershaw/Sherzer type makes it to free agency I'd be allllllll about jumping on that, locking them up with some big money and save are reservoir of young pitching prospects to supplement the rotation.

Lackey going into 2015 making the MLB minimum will have tremendous trade value, especially to a small-market contender.

In fact, if you think about the logic of the abstract economics, trading him becomes theoretically irresistible. Dealing him for another guy a year from free agency who had the same excess value would be trading for a much better pitcher, because that guy would be making a third-year arbitration salary. Put another way, swapping him for an equal pitcher would save the other team a lot of money, and in theory they'd throw in a good prospect to square the deal. No matter how you slice it, you should be able to get back more in talent than you give up.

How this plays out in practice will depend on the quantity and quality of the young starting pitching. One likely scenario is that from Owens, Webster, Ranaudo, De La Rosa, Barnes, Workman, and Wright, two or three project to be solid MLB starters in 2015. In that case, it would make sense to deal Lackey, essentially opening up a spot to sign or trade for someone you thought was even better. If three or four guys project to be solid, to that we appear to have excess pitching SP depth, Cherington's phone will be ringing off the hook.

This will be a unique situation -- a guy in consideration for a qualifying offer the following year who is making the MLB minimum -- and it will be interesting to see if the Sox exploit it in a unique way. In any case, I think it makes it more likely that they'll be shopping for some kind of SP addition for 2015.