On Thursday, the stakes are even higher for Epstein and the Cubs, who have the second pick overall in the Draft.
The Astros have been on the clock since the 2012 regular season ended. So has Epstein, player development and scouting director Jason McLeod and amateur scouting director Jaron Madison. Epstein never had a pick this high in his nine years as general manager with the Red Sox.
The 2013 First-Year Player Draft will take place Thursday through Saturday, beginning with the Draft preview show on MLB.com and MLB Network on Thursday at 6 p.m. ET. Live Draft coverage from MLB Network's Studio 42 begins at 7 p.m., with the top 73 picks being streamed on MLB.com and broadcast on MLB Network. Rounds 3-10 will be streamed live on MLB.com on Friday, beginning with a preview show at 12:30 p.m., and Rounds 11-40 will be streamed live on MLB.com on Saturday, starting at 1 p.m.
MLB.com's coverage includes Draft Central, the Top 100 Draft Prospects list and Draft Tracker, a live interactive application that includes a searchable database of Draft-eligible players. You can also keep up to date by following @MLBDraft on Twitter. And get into the Draft conversation by tagging your tweets with #mlbdraft.
The last time the Cubs had the second overall pick was 2001, when they chose pitcher Mark Prior after the Twins selected catcher Joe Mauer. Prior finished seven in the National League Rookie of the Year Award voting in 2002, and he won 18 games the next year, helping the team get to the playoffs.
The Cubs have narrowed the field to a final four: pitchers Jonathan Gray of Oklahoma and Mark Appel of Stanford and third basemen Kris Bryant of San Diego and Colin Moran of North Carolina.
It's no secret the organization needs more pitching. Do they take a pitcher or a position player at No. 2?
"Ultimately, it's [a] long-term [decision] -- who will make the most significant impact on the organization?" said Jason McLeod, senior vice president, scouting and player development. "We don't go into any Draft drafting based on need. We go in drafting on who we feel is going to provide the biggest impact for our club, hopefully for years to come. Whether you're picking sixth, like last year, or [No.] 2, or in Boston, late in the first round, that's always the mindset. The player pool changes a lot when you're picking at the top of the Draft."
Manager Dale Sveum has been watching video of the quartet. Although many mock drafts suggest Gray and Appel will be the first two players taken, Sveum also was impressed with Bryant and Moran. Bryant, a right-handed batter, hit 30 home runs entering conference tournament play, and he played for Team USA over the summer. Moran, a left-handed batter, is considered more of a pure hitter than Bryant.
"[Moran] is another polished-type hitter at that age already," Sveum said. "He has a Robin Ventura-type swing and presence at the plate. He has really good plate discipline and not really the power numbers that Bryant can put up. Bryant is a big [guy], 6-foot-5, [with] some kind of leverage at the plate. Two different hitters -- one's right, one's left. It's fun to watch them."
Sveum has seen video of Gray and Appel, too.
"They're pretty special arms," Sveum said. "They're two different guys. Appel is so advanced as far as his secondary pitches, and Gray can just power you away with easy life on the fastball. It looks like it's showing 85 [mph] and it's 100.
"They're both pretty good," he said. "I don't know if one separates from the other one."
Here's a glance at what the Cubs have in store as the Draft approaches:
In about 50 words
Since Epstein took over as president of baseball operations, the emphasis has been improving the pitching and finding impact players, such as highly regarded Cuban outfielder Jorge Soler. In last year's Draft, they took pitchers with seven of the first eight picks. The exception was No. 1 pick Almora, an outfielder who they hope will develop into a star.
Heading into the final week, the Cubs had narrowed their list to four players: Gray, Appel, Bryant and Moran. Epstein led a contingent of Cubs officials to Oklahoma to meet with Gray in mid May. All but Appel reached the first round of the NCAA tournament, providing the staff with one more look before Thursday. Epstein and McLeod have led contingents to meet with the players and ask questions face-to-face, which McLeod said will help in the ultimate selection.
Chicago has taken a position player in five of the past eight years in the first round (Tyler Colvin, 2006; Josh Vitters, '07; Brett Jackson '09; Javier Baez '11; Almora '12). In Epstein's tenure as general manager, he's never had a selection in the top 10, but he and McLeod have made smart picks, taking Dustin Pedroia in the second round in '04 and Jacoby Ellsbury 23rd overall in '05. Those are the type of impact players they Cubs are looking to draft.
Under the Collective Bargaining Agreement, each team has an allotted bonus pool equal to the sum of the values of that club's selections in the first 10 rounds of the Draft. The more picks a team has, and the earlier it picks, the larger the pool. The signing bonuses for a team's selections in the first 10 rounds, plus any bonus greater than $100,000 for a player taken after the 10th round, will apply toward the bonus-pool total.
Any team going up to five percent over its allotted pool will be taxed at a 75-percent rate on the overage. A team that overspends by 5-10 percent gets a 75 percent tax plus the loss of a first-round pick. A team that goes 10-15 percent over its pool amount will be hit with a 100 percent penalty on the overage and the loss of a first- and second-round pick. Any overage of 15 percent or more gets a 100 percent tax plus the loss of first-round picks in the next two Drafts.
"This is the new system we're in, so ultimately, it has a big impact on what you're doing throughout the Draft," McLeod said. "I think last year you saw teams take a different approach -- like what Houston did last year, and somewhat what we did last year -- you take college seniors a little later and look for places to save money. There were some teams that played it straight and went straight through the slots.
"I think every organization has what they feel is going to be best for them," he added. "We're not going to go into our first selection with [signability] in mind. It's not going to be about signability; it's going to be about the best player for the Cubs. We do have the player pool to deal with, and I think as you get deeper in the Draft, strategy plays a part of it."
The Cubs' bonus pool is $10.5 million, with $6.7 million alloted for the first-round pick, $1.36 million for the second round selection, and $736,200 for the third round pick.
Pitching, pitching and more pitching would be nice to add to the Minor League system. But the Cubs also are looking for players who know the value of quality at-bats.
"Theo and I believe strongly that you can't be a good team if you don't get on base and grind out at-bats," general manager Jed Hoyer said. "If we're not going to do that, we'll have to spend a lot of time figuring it out. We won't be successful until we do."
The Cubs could've picked Appel last year but had spent the most time with Almora. Former Cubs pitcher John Koronka was the area scout who befriended Almora's family. Epstein believes in being very thorough, and knowing a player's character and background as well as his talent. It will be interesting to see which area scout is linked to this year's No. 1 pick.
• Recent Draft History •
Javier Baez, the No. 1 pick in 2011, had an impressive Spring Training, batting .298 with four home runs, including two not included in the stats against Team Japan in an exhibition game. Baez showed he still has work to do, batting .241 against right-handed pitchers compared to .389 against lefties. He opened at Class A Daytona but could move up quickly.
Nick Struck, 23, was the Cubs' 39th-round pick in 2009. In his first full season in the Minor Leagues in '10, he threw a no-hitter for Class A Peoria, which was then part of the Cubs organization. Last year, the right-hander led the Southern League with 14 wins pitching for Double-A Tennessee. In the past two seasons, he's walked 88 while striking out 234 over 303 innings. Struck was named the Cubs' Minor League Pitcher of the Year last season.
In The Show
On the current 40-man roster, players drafted by the Cubs include pitchers Jeff Samardzija (fifth round, 2006), James Russell (14th round, '07), Brooks Raley (sixth round, '09) and Chris Rusin (fourth round, '09). The position players on the 40-man who were selected by the Cubs include second baseman Darwin Barney (fourth round, '07), infielder Vitters (first round, '07), infielder Logan Watkins (21st round, '08), outfielder Jackson (first round, '09) and outfielder Matt Szczur (fifth round, '10).
Cubs' recent top picks
2012: Almora, OF, Class A Kane County 2011: Baez, SS, Class A Daytona 2010: Hayden Simpson, RHP, SIU Miners, Frontier League 2009: Jackson, OF, Triple-A Iowa 2008: Andrew Cashner, RHP, Padres, (traded Jan. 6, 2012)