Going Back in Time to October 2007, Vol. II: The Drafts

If you haven't heard, I'm almost ready. I'm putting the finishing touches on my time machine and preparing to go back to October 2007 to use the benefit of hindsight to fix everything the Boston Red Sox have done since that point. In Vol. I, I went over the obvious mistakes, identified some buy-low and sell-high candidates, and fixed the squads as best I could in 2008 and 2009. Now before I move on to 2010 and beyond in Vol. III, I have some comments to make about the drafts.

Note: Below several references will be made to the current top prospects lists by John Sickels at and by Baseball America.

V-Mart, Beltre, Crawford and the 2011 Draft

Before I move on from the 2009 season in a sequential manner, I want to take note on a couple important transactions that take place around this time. Then I'll segue into discussion of the amateur drafts that occurred in this period, which begin to affect the major league club already in 2010.

The transactions I mean to discuss now are, for one, the acquisition of catcher Victor Martinez from the Cleveland Indians at the 2009 trade deadline in exchange for Justin Masterson, Nick Hagadone, and Bryan Price. Martinez' contract at the time included a club option for the 2010 season. And another transaction is the signing of free agent third baseman Adrian Beltre to a one-year contract for 2010, which turns out to be quite a deal.

Because acquiring these players and then losing them to free agency after 2010 netted the Red Sox four high picks in what appears to be one of the greatest draft classes ever (at least for the first and supplemental rounds), I'm hesitant to mess with that, even if it means, in V-Mart's case, losing Justin Masterson. Draft positions, of course, will not be the same, as we will have hopefully bent the standings in the Red Sox' favor. But for argument's sake, let's look at the 2011 draft as it occurred in our timeline.

Because V-Mart came and left, we got Barnes at #19 and Owens at #36. Because Beltre came and left, we got Swihart at #26 and Bradley at #40. It is amazing, but even in the hindsight afforded to us so far, we could not have done better with those picks. Also necessary to mention, not signing Carl Crawford would give us another first-round pick in the 2011 draft (#24), the one the Rays used -- properly, I believe -- for pitcher Taylor Guerrieri. Re-signing Beltre after 2010, certainly an option worth entertaining given his excellent play, would mean sacrificing Guerrieri along with one of Swihart, Owens, or Bradley (assuming we retain pick #24), not to mention blocking Will Middlebrooks in just the second year of Beltre's contract. I wouldn't think that preferable.

There is something else important to consider regarding Carl Crawford. If the Red Sox don't sign him and give the Rays the 24th pick in the 2011 draft, which of course they won't in our revised timeline, the Angels would probably have signed him and given the Rays the 17th pick. That potentially could put our pick of Matt Barnes at #19 in danger. The Rays could choose Barnes, but also on the board was pitcher Sonny Gray, whom the A's chose at #18. Somehow I think that the Rays might prefer him, as, though he is right-handed, Gray bears a resemblance to David Price in that both were Vanderbilt juniors with high pedigrees. Like Barnes, Gray was originally expected to be picked higher than he was and dropped only because of the depth of the class. Or maybe the Rays could still have gone with Guerrieri if that's who they liked regardless. Indeed, today Guerrieri is esteemed a better prospect. But if the Rays get Gray at #17, the A's could grab Barnes at #18, leaving the Red Sox at #19 to choose ... second baseman Kolten Wong, whom the Cardinals picked at #22. Wong is an excellent prospect, whom Sickels ranks higher than Barnes at the moment, at #29 compared to Barnes at #41, though Baseball America has Wong at #44, compared to Barnes at #13.

But for now, for convenience's sake, I'm going to assume, with the Martinez and Beltre deals done and the Crawford deal not done, that the Red Sox get five top-40 picks in the 2011 draft, and use them for Barnes, Guerrieri, Swihart, Owens, and Bradley. If you think we'll miss Barnes, given the scenario I described, then we settle for Wong instead. All of this is speculation gone wild, of course, as for one thing I hope the Red Sox' first-round pick is lower than #24.


But now that we've talked about as much as we can about the 2011 draft (given the uncertain returns of the later rounds), let's look at the earlier drafts and see what we can do to build a better franchise. I mean, the original inspiration behind my trip was to correct all the errors, but we might as well use the opportunity to steal a bunch of great young prospects, or just to increase value wherever we can.


The 2008 Amateur Draft

Immediately in the first round of the 2008 draft, an interesting decision presents itself on whether to go with either of two college pitchers Lance Lynn or Wade Miley (both All-Stars this year) at pick #30, instead of high schooler Casey Kelly. Now, Casey Kelly's high prospect status was cashed in by the Red Sox in the Adrian Gonzalez trade. It appears they may have successfully sold high on him, as since then he has been less than stellar and his stock has fallen. Looking at the early statistical returns of Lynn and Miley, I get the sense that Lynn might be a slightly better pitcher, but the separation between the two is as small as the sample sizes of their careers so far. Lynn, it should be said, had a better prospect pedigree, and that probably should settle the debate in his favor. Hopefully the difference in development, switching him from St. Louis to Boston, would not be significant.

But the value of either Lynn or Miley has to be weighed against what was achieved with Kelly. The winter the Gonzalez deal went down, Baseball America ranked Kelly #31 among their top 100 prospects, a list neither Lynn nor Miley appeared on. The decision of giving our rose to either Kelly or Lynn comes down to whether you would do again the Gonzalez deal, knowing what you know now in July 2012. For now I'll say I would be reluctant to make a conclusion on my own, but I'll revisit this topic under the 2011 season.

Not too dissimilarly, in the sandwich round at #45 you have Bryan Price, who a year later was included in the package sent to Cleveland for Victor Martinez. Still on the board at that point, however, are current fringe Major Leaguers (counting down the draft tracker) Johnny Giavotella, Xavier Avery, Robbie Ross, Tyson Ross, and Tyler Chatwood -- all of them more valuable than Price, who I would think could easily be replaced in that trade. Though Robbie Ross isn't bad, I think there are better options going further down the draft tracker, so save this pick for now.

At #77 instead of Derrik Gibson there are better alternatives soon following: Jordy Mercer and ... um, Zach Stewart ... who at least has been a valuable trade piece several times now. But save this pick, too; it gets better.

The best deals begin appearing after pick #85 when instead of Stephen Fife (traded to the Dodgers last year in the Bedard deal) you could have Danny Espinosa, the current second baseman for the Washington Nationals. At this position is also available Brent Morel who could be a valuable trade piece circa 2010.

But even better options arise before the Sox' next pick: Craig Kimbrel, Vance Worley, and Kirk Nieuwenhuis. So instead of Price, Gibson, and Fife at picks #45, 77, and 85, I would go with Kimbrel, Worley (we need pitching), and Espinosa.

Instead of Kyle Weiland in the third round, at #108, we could go Dee Gordon, Brandon Crawford, or perhaps current Padres prospect Joe Wieland. And at #142 instead of Peter Hissey we could have Daniel Hudson, Alex Avila, Anthony Bass, Tyler Pastornicky, or Collin Cowgill. I'd use these two picks on Hudson and Avila, who were both quite valuable before this year.

Would you want to mess with the fifth-round pick (#172), Ryan Westmoreland? You could have the Pirates' Josh Harrison or the Blue Jays' Eric Thames. I say no way. Pick him, sign him, and immediately alert the doctors about his brain.

Nor would I change three of the next four picks, all catchers: Ryan Lavarnway in the sixth round (#202), Tim Federowicz in the seventh (#232), and Christian Vazquez in the ninth (#292). A pretty good class of catchers to go along with Alex Avila. In the eighth round (#262), instead of Michael Lee, I'd go with the lefty Tommy Milone, recently traded by the Nationals to the A's in the Gio Gonzalez deal. I'm not high on Milone at the moment, but he is pitching in the majors.

I'll keep going as long as I find deals. At #322 in the tenth round, instead of Pete Ruiz, Nate Eovaldi. With the next two picks (#352 and 382) you can have the Cubs' Tony Campana and the Yankees' David Phelps. At #412 (13th round) you can have the Phillies' Michael Schwimer. The Nationals' Tyler Moore is a good value at one of the next two picks, #442 or 472 -- as is the Nationals' Steve late as Boston's pick at #562 in the 18th round. (A really good job by the Nationals here; no one else is getting anything out of these rounds.)

Instead of wasting the 20th-round pick (#622) on Alex Meyer who won't sign, you could have Lucas Luetge who the Mariners plucked from the Brewers in last winter's Rule-5 Draft. They would probably do that again, though, and come to think of it, we might lose a number of players to the Rule-5 Draft because our 40-man is going to be stacked.

Ryan Cook, the A's one All-Star this year, who they got from the D-Backs in the Cahill trade, could be had by the Red Sox as late as #802 (26th round). Pitching prospect Jarred Cosart, traded to the Astros by the Phillies for Hunter Pence, could be had by the Red Sox as late as pick #1132 (37th round). Cody Eppley, who the Yankees claimed off waivers from the Rangers at the beginning of this season, could easily be picked by the Red Sox in the 42nd round, but since he was available to everybody as late as this spring, why bother?

And with the second-to-last-round pick* in the 2008 draft, I'd without a doubt pick the would-be undrafted Brandon Beachy out of Indiana Wesleyan University. What a benefit hindsight can be, eh? To our 2011 rotation depth we just added Daniel Hudson, Brandon Beachy, and Vance Worley, at no extra cost. No sir, we will not be missing John Lackey. You'd have to plan around Hudson's and Beachy's 2012 Tommy John surgeries, though.

*With the last pick, I'd still go with Kyle Stroup, even though he has lost two seasons now to ACL tears in first one knee and then the other. He's still better than what you got in the round before.


The 2009 Amateur Draft

Later drafts begin to get harder and harder to evaluate and plan for as outcomes for prospects become less certain and altered standings and compensation picks will mix up the draft order. In the first round of the 2009 draft, at pick #28, the Red Sox chose Reymond Fuentes whom they included in the package for Adrian Gonzalez. Would you rather've picked Tyler Skaggs (ranked most recently by Baseball America as the #7 overall prospect; Sickels has him at #20)? Brett Jackson? Garret Richards? These are better prospects, but even three years later, still prospects. Jason Kipnis is one name that pops up as definitely desirable, but who's to say at this point that he's better than some of the others who have yet to develop? Eh, in retrospect, I'd go with Kipnis. Or I could be talked into Skaggs.

In the second round at #77, instead of Alex Wilson, currently doing just okay in his long forecasted transition to the bullpen, the best deal I think is the Royals' Wil Myers. In Sickels' most recent rankings, Myers is the #2 overall prospect; Baseball America has him #3. I'll sure take that over Wilson. Kyle Seager is also both available at that spot and better than Wilson, but Myers is best.

David Renfroe was picked in the third round, Jeremy Hazelbaker in the fourth. Brandon Belt, chosen by the Giants in the fifth round would be preferable to either. Since Hazelbaker is better than Renfroe, it should be Belt and Hazelbaker.

Brandon Jacobs in the 10th round was a good value. So was Miles Head in the 26th round (traded with Reddick to the A's -- something not to do again).

At #438, in the 14th round, Drew Hutchison would be a better value than William Holmes. Meanwhile in the 22nd round, someone named Jordan Flasher was chosen (released by the organization last year) when Slippery Rock's Matt Adams was still on the board. In the 32nd round the same Trey McNutt of the Cubs that Red Sox fans were wondering about this off-season could have been chosen instead of Michael Clark.

In the 33rd round the Red Sox should still choose high school pitcher Willie Tart, because that name is awesome -- and though still on the board is high school pitcher Malcolm Clapsaddle (which is about the only name possible that could top it), Mr. Clapsaddle does not sign but goes to college and becomes available again in the 2012 draft. We can have both Willie Tart and Malcolm Clapsaddle!


The 2010 Amateur Draft

First off, do not pick Kolbrin Vitek. He is a bust.

Before getting into the rest of the 2010 draft, though, there are compensation scenarios to unravel. After the 2009 season the Red Sox lost picks for signing John Lackey and Marco Scutaro, but gained picks in letting go Jason Bay and Billy Wagner -- all four of which were Type-A free agents. Catching-and-releasing Billy Wagner was very smart. Assuming even hindsight isn't enough to keep Manny Ramirez happy and productive, the Jason Bay trade was a deft one, and not re-signing him was too. Of course, the Lackey mistake will not be re-made.

If, as I suggested above, the Red Sox can beat Toronto's offer to Oakland for Marco Scutaro after the 2007 season, signing him after the 2009 season would not cause a loss of draft picks. There would be the option of letting Scutaro go and getting two more draft picks, but I think I'd prefer either not to have to replace his production over 2010-2011 or to use him as a trade chip during that time.

So here's the difference in draft picks that those free agency moves made:

For Jason Bay, the Red Sox received the Mets' second-round pick, which ended up being #57, because their first-round pick was protected. For Billy Wagner, the Red Sox received the Braves' first-round pick, which at #20 would be the highest pick for them under any scenario (wasted on Vitek). Two sandwich picks were allotted for Bay and Wagner, and they ended up being #36 (Bryce Brentz) and #39 (Anthony Ranaudo). Because we signed Lackey and Scutaro, we lost our original first- and second-round picks, which ended up being #29 and 80, and Anaheim and Toronto each received a sandwich pick for them as well (which pushed back two spots one of our sandwich picks as well as all picks thereafter).

Had picks not been lost on account of the Lackey and Scutaro signings, instead of only picks #20, 36, 39, and 57 through round two, the Red Sox would have had #20, 29, 36, 37, 55, and 78. Let's look now at what we can get with those six picks and beyond into the later rounds. For simplicity's sake we'll have to ignore that the draft order will be different based on our manipulations over the previous two years.

At #20, instead of Kolbrin Vitek, we have many prospects to choose from including Christian Yelich and Zach Lee, the two of whom would not be available by the time pick #29 comes around. At #36 we might not still want Bryce Brentz; he's not a bad pick, but there are, in fact, better. At #37 we can surely do better than Anthony Ranaudo. According to Sickels' most recent rankings, the top four prospects available in this draft between picks #20 and 55 and not afterwards are Taijuan Walker, Nick Castellanos, Christian Yelich, and Mike Olt, with Noah Syndergaard and Zach Lee close behind. Baseball America agrees but is much higher on Olt, lower on Syndergaard and Lee.

Well, both Yelich and Lee could not both be attained with our picks, so I would definitely go with Yelich at #20, and Walker and Castellanos at #29 and 36. At #37 the best choice appears to be the college third baseman Mike Olt (Syndergaard is a young pitcher in the Blue Jays' system, so is certain to be badly injured). Man, what a bad choice Vitek was.

With the Mets' second-round pick, the Red Sox chose pitcher Brandon Workman. But still on the board are Andrelton Simmons, Jedd Gyorko, and Cody Buckel, all of whom are better, but Simmons by far the best.

At #78, with the Red Sox' original second-round pick (lost to Toronto), I would recommend picking up current White Sox closer Addison Reed.

In the third round the Red Sox chose Sean Coyle, which perhaps is a good pick, but still on the board are another second baseman Eddie Rosario, a top prospect in the Twins organization, and pitcher A.J. Cole, recently included in the Washington deal to Oakland for Gio Gonzalez. In the fourth round the Red Sox chose Garin Cecchini, but two picks later the Yankees chose the more highly regarded Mason Williams (rated #28 overall by Baseball America, #37 overall by John Sickels). I like Cecchini and Coyle, but I would prefer Rosario and Williams at these spots, in retrospect. And scooping a top Yankees prospect provides extra incentive. Let's see if we can't do that again, and soon...

Keith Couch in the 13th round is a good value. Or he would be if two picks later the Yankees didn't pick Tyler Austin, currently one of their top prospects (Baseball America's #39 overall, Sickels' #67). Fortunately the Red Sox can easily have both Couch and Austin by picking them anywhere before the 13th round.

For the other later rounds, I have no grand ideas. Mathew Price should be avoided in the eighth round, for future disciplinary reasons. In his place you can get Aaron Kurcz, because hopefully that whole compensation fiasco can be avoided.

And in the very late rounds a guy named Dale Cornstubble is available. I imagine he and Malcolm Clapsaddle would get along well in the clubhouse. Or if to the contrary they were rivals -- perhaps fighting over the affections of Willie Tart -- the Cornstubble-Clapsaddle fracas would be epic.


Coming up next, now that we've supplied our system a little better, I'll pursue all the right moves for the 2010 club and beyond in Vol. III.

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