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July 15, 2020 at 12:30 PM

Revisiting the 2007 draft: Anthony Rizzo & success with mid-round prep players

Thank you for checking in on the newest entry in our draft retrospective series. Yesterday was a pick-by-pick rundown of 2007, while today we will dig a little deeper into a few of the more interesting and prominent draftees. For a quick list and links to player pages, check out our Draft History page.

2007 MLB Draft

It was too early to know that the 2005 and 2006 drafts would be successful ones for the Red Sox, but Scouting Director Jason McLeod had to know the task would be tougher in 2007 after the Red Sox sacrificed their first-round pick to sign shortstop Julio Lugo. The departure of free agents Alex Gonzalez and Keith Foulke in free agency did help to offset this loss, netting two supplemental round picks. Gonzalez hit .245/.286/.401 over the rest of his career and Foulke, made expendable by Jonathan Papelbon's breakout 2006 season, threw only 31 more innings for the Athletics before retiring. The class's depth took another hit when second-round pick Hunter Morris went unsigned after disagreements on pre-draft agreement. 

Despite losing out on the 20th overall pick and a mixed bag with their top pick, the Red Sox came away from 2007 with a quality draft.  The team had six signed players that made it to the majors, despite having only one of the first five picks ever reach the SoxProspects.com Top 10. Much of the success is due to the stellar performance of Anthony Rizzo. Nearly all of the draft's major league successes have come wearing a non-Boston uniform, but the goal of the draft is to draft and sign the best talent without any guarantee where that talent will be used. In the case of this draft, some of it was used to acquire major league talent, while other players did not realize their full potential until with other major league organizations. 

The Vitals
General Manager: Theo Epstein
Scouting Director: Jason McLeod

Major Leaguers drafted and signed
Anthony Rizzo (6th round, 33.5 bWAR)
Ryan Pressly (11th round, 6.7 bWAR)
Hunter Strickland (18th round, 4.0 bWAR)
Drake Britton (23rd round, 0.5 bWAR)
Nick Hagadone (1st round, -0.2 bWAR)
Will Middlebrooks (5th round, -0.7 bWAR)

Unsigned players who reached the major leagues
Yasmani Grandal, 27th round, 17.2 bWAR)
Nick Tepesch (28th round, 0.4 bWAR)
Justin Grimm (13th round, -2.4 bWAR)

Compensation considerations
Surrendered first-round pick for the acquisition of free-agent shortstop Julio Lugo
Received supplemental round pick (55 overall) for loss of free agent Alex Gonzalez
Received supplemental round pick (62 overall) for loss of free agent Keith Foulke

High school success
With very few exceptions, prep players are regarded as more risky and volatile than college players. They are often more raw, without the high-end coaching offered to college players, and have a longer developmental path. Aside from the baseball risks, these are 17- and 18-year-old kids who are making a huge jump into a career with many having never even lived away from home or had to be self-reliant.

That makes it all the more surprising and impressive that the majority of the return from this draft came from high school players. Among the players the Red Sox drafted and signed who played in the majors, only first pick Nick Hagadone was selected out of college. In 2006, the only players signed out of high school who made the majors were Lars Anderson (-0.3 bWAR) and Ryan Kalish (-0.6 bWAR), in 2005 it was Michael Bowden (0.8 bWAR), and in 2004 there were no such players. 

Not signing Morris, the second-round pick, was not in the plan since the club thought it had a pre-draft deal with him and believed he was trying to increase his bonus demands after being drafted. Morris' camp on the other hand said there was never such an agreement. The focus of the staff now turned to other high school players taken later in the draft. Austin Bailey ($285,000), Hunter Strickland ($123,250), and Drake Britton ($700,000, pictured above left) all commanded large bonuses relative to their draft pick. Britton and Strickland developed into major leaguers, and Bailey remains a big what if after tearing his labrum in his very first professional start. 

Sometimes, when you do not have early picks to allow you to take safe players, teams are willing to take more risk, and that is what the organization did here. They were able to reallocate draft capital, and with those additional darts, were able to hit on major league talent.

Positional stars
The Red Sox just missed the rare chance to get two stars at their respective positions out of one draft, first baseman Anthony Rizzo (pictured, top right) and catcher Yasmani Grandal. These two players chose different paths after being selected in 2007, but shared a lot in common in their rise to be All-Stars.

Rizzo was selected in the sixth round out of Stoneman Douglas High School in Florida and signed for $325,000. He first cracked the SoxProspects.com Top 10 after hitting .298/.365/.494 over the first half of the 2009 season as a 19-year-old at Greenville in his return from Hodgkin's Lymphoma, treatment for which cost him almost all of the 2008 season. He then kept up that pace in Salem to finish the year, with a .295/.371/.420 line. After posting an OPS over .800 at both Salem and Portland in 2010, he started getting national attention, ranking as the 75th best prospect in the game by Baseball America entering the 2011 season. He also got attention from the San Diego Padres, who now had former Red Sox front office members Jed Hoyer and Jason McLeod running things. He was one of two centerpieces, along with Casey Kelly, in the trade that landed the Red Sox first baseman Adian Gonzalez

San Diego put Rizzo right in the big leagues and he struggled. With Hoyer and McLeod now joining Red Sox former GM Theo Epstein with the Cubs, they traded for Rizzo again, this time for future Red Sox pitcher Andrew Cashner. Rizzo's first two seasons with the Cubs were an adjustment as he hit a fairly pedestrian .251/.330/.435 over 2012 and 2013. That is where the struggles would end. Over the next six years, he would cement himself as a threat in the middle of the Cubs lineup and one of the best first basemen in the National League. He hit .284/.388/.513 with 179 home runs, three All-Star appearances, a World Series Championship, and three Gold Gloves (despite mixed defensive metrics).

Grandal did not sign, instead opting to develop at the University of Miami, where by his junior year he was a member of Team USA and a First-Team All-American putting up video game numbers, hitting .401/.528/.721. He was selected 12th overall by the Reds in 2010 and, just like Rizzo, was on national Top 100 prospect rankings prior to the 2011 season and was traded to San Diego, albeit before the 2012 season.

San Diego got him to the majors midway through his first year and he struggled in a different kind of way—in 2013, he was suspended for 50 games for an elevated testosterone level, then tore both his MCL and ACL. He was moved to the Dodgers, where he put up a .790 OPS over four years, very good for a catcher. In 2019, he really exploded, hitting .246/.380/.468 and earning a four-year, $70-million deal from the Chicago White Sox this offseason, cementing his status as one of the best catchers in the game.

One signed, one didn't, but they both ended up with stints in San Diego, now reside on opposite sides of Chicago, and are among the game's best.

Good relievers born from prep starters
The volatility of high school players was discussed earlier, and it is even more pronounced with high school pitchers. In addition to all the previously mentioned risks, with pitchers, the additional health risk of Tommy John surgery always looms as a possibility. High school pitchers are almost never moved immediately to the bullpen, but they begin their professional career as starters and are only moved to the pen if starting does not suit their skillset. 

Ryan Pressly (pictured, left) signed out of high school and faired well as a starter in the Gulf Coast League, Short-Season Lowell, and Low A Greenville. However, when he advanced to High-A in 2011, he struggled and then again in 2012 while repeating the level. Midway through 2012, he was moved to the bullpen and fared much better, cutting his ERA by more than a run after moving, despite a promotion to Portland soon after making the change. With his increased success at a new level in a new role, Minnesota saw something in him and selected him in the Rule 5 Draft that offseason and messed with his pitch mix a bit, eliminating his changeup and having him increase his use of his curveball and slider. Over his time with the Twins, his velocity increased and so did strikeout rate, almost doubling over his career. Now in his 10th major league season and now with the Astros, who got him to throw his curveball even more, increasing it to the point he uses it more than his fastball, he has a career 3.38 ERA and 0.90 WHIP and six strikeouts for every walk.

Drafted a few picks later, Hunter Strickland was another high school kid with an eye on starting. Aside from 25 innings his draft year, he threw two seasons for Red Sox affiliates, mostly as a starter, and did quite well with a 3.18 ERA at Lowell in 2008 and a 3.35 ERA at Greenville in 2009. Pittsburgh then acquired him in the Adam LaRoche deal and he was on the move again when the Giants claimed him off waivers. He was always a candidate to move to the bullpen as he struggled against lefties, and he was briefly moved to the bullpen at the start of 2013 before succumbing to Tommy John surgery. From 2014-2018, the role suited Strickland well as he posted a 2.91 ERA over 226 innings. Despite Strickland struggling in 2019, he went on to win his second World Series after a trade to the Nationals after winning it as a rookie with the Giants in 2014.

It took role changes, pitch mix changes, surgeries, and team changes, but the rollercoaster still resulted in the improbable outcome of two high school draft picks turning into good relievers over the last six years.  

Developed into top prospects
A couple Red Sox 2007 draft picks developed into top prospects, one from an earlier round and one from a late-round. Third baseman Will Middlebrooks (pictured, right) instantly popped onto the SoxProspects.com radar and was ranked 12th by September of his draft year despite not playing in a game. From there, his stock was either holding or even dropping off a little as he hit some growing pains in 2008, 2009, and 2010 rising through the various levels of A-ball. In 2011, Middlebrooks started the season ranked 13th, but after raking in Portland, showing real power for the first time and hitting .302/.345/.520 at 22 years old, he finished the year as the top-ranked prospect in the system, jumping over outfielder Ryan Kalish and staying ahead of future top prospect Xander Bogaerts.

Now ranked nationally in all the top 100 prospect rankings, he again made easy work of Triple-A in 2012 with a 1.057 OPS over 24 games. Promoted to the majors when Kevin Youkilis went down with an injury, Middlebrooks hit .326 with 37 RBI over his first 41 games, and his performance was so strong that when Youkilis returned, they initially split time before the Red Sox ultimately decided to trade the oft-injured veteran. From then on, Middlebrooks struggled. In 2013, he lost time to Jose Iglesias and ultimately Bogaerts, who made his debut that year while splitting his time between third and short. Despite being passed by, Middlebrooks still played and won the 2013 World Series. The acquisition of free agent third baseman Pablo Sandoval that offseason signaled that Middlebrooks' departure from the team was nigh, and he was dealt to San Diego later that year. Even though the peak was brief, Middlebrooks still developed into the top prospect in the system and a major leaguer.

Another 2007 draft selection who slowly developed into a highly ranked prospect was righty Drake Britton. He wanted top-two-round money to sign, and after an inconsistent spring, most teams were not willing to give it to him. That is what enabled the Red Sox to snag him in the 23rd round, and their second-round pick going unsigned possibly freed up the money to pay Britton $700,000. While Middlebrooks' rise was a bit more steady, Britton's was a bit of a roller coaster. His career started off with Tommy John surgery in October 2008, which caused him to miss most of 2009. After pitching well in late 2009 and 2010, he rose to number 10 on the SoxProspects.com rankings by year-end, and after trades and other shuffling, was up to fourth by the start of 2011. That year in Salem, Britton took a big step back, walking 55 over 97 2/3 innings with a 6.91 ERA, highest in the league, and dropped all the way to 16th in the rankings.

Despite the poor performance that year, the Red Sox decided to add Britton to the 40-man roster to protect him from the Rule 5 Draft, which came up quickly after the missed time due to Tommy John, a scenario eerily reminiscent of what is about to happen to current prospect Jay Groome. He struggled while repeating Salem, but had success upon a seeming change-of-scenery promotion to Portland, with a 3.72 ERA over 16 starts, putting him back in the SoxProspects.com top 10. In spring training 2013, Britton was arrested for a DUI, he but managed to work his way up to the majors that year pitching out of the bullpen, where he was better suited. The bullpen roster over the next couple years was a bit tight, and it resulted in the Red Sox being forced to use up Britton's options before he had time to fully develop. In February 2015, he was claimed by Theo Epstein and the Chicago Cubs. The Cubs tried Britton as a starter but it did not work out and he was released about two years after joining the Cubs. Another example of the volatile nature of high school starters turned relievers, Britton managed to rise from a 23rd-round pick to a top-five player in the system and major leaguer.

Missed opportunities
The club's biggest regret in the draft is probably not getting Grandal to sign, though the move was certainly the right one for him, as discussed. The other standout missed opportunities came in the supplemental round. The Red Sox had two shots at it and twice passed on future superstars who would be in the major leagues at only 20 years old, as outfielder Giancarlo (Mike back in those days) Stanton went 76th overall and first baseman Freddie Freeman went two picks later. A mere three years later, both were already playing in the big leagues. Stanton took no time to get acclimated, posting an .800+ OPS in his rookie season for the Marlins. After 10 seasons, he has a 40.4 bWAR and is still one of the most dangerous hitters in the game. Freeman got just a cup of coffee in 2010, but in 2011 he found his footing, and in 10 major league seasons, he has a 35.7 bWAR and is coming off a 2019 season which was the best of his career.

Red Sox missed on one pitcher that most other teams missed out on as well. In 2007, Corey Kluber went in the fourth round, 134th overall. Over his nine-year major league career, Kluber has a 32.2 bWAR, 3.12 ERA, 1.09 WHIP, and 9.8 strikeouts per nine innings while winning two AL Cy Young awards along the way.

Another missed opportunity comes with a couple players that the Red Sox should have tried to retain. As mentioned above, Rizzo was a very good prospect for the Red Sox and was part of the cost to obtain a veteran star in Adrian Gonzalez. It didn't work out as planned for the Red Sox, as Gonzalez had a monster year in 2011 but was ultimately never happy in Boston and traded after just 18 months (although his value is what allowed the club to move the Carl Crawford and Josh Beckett contracts). In retrospect, I am sure the Red Sox would have rather had the player that Rizzo grew into, especially on his entry deal and the subsequent team-friendly eight-year deal he signed after. 

Final thoughts
For a draft with no first-round pick and a second-round pick who went unsigned, the Red Sox managed a solid haul. They drafted and signed six major leaguers and one star in Anthony Rizzo. The Red Sox used some of the capital from this draft to acquire other major league talent and build up what became the second-best farm system in 2008 according to Baseball America. This draft is the perfect reminder that talent and prospects can come at any point in the draft, not just in the first round. 

Photo Credit: Anthony Rizzo, Drake Britton, and Ryan Pressly by Kelly O'Connor.

Will Woodward is a Co-Owner and Senior Staff Writer for SoxProspects.com. Follow him on Twitter @SPWill.