Theo Epstein's All-Star imprint? 11 players, ages 22 to 40, from Boston to Chicago

ByJerry Crasnick ESPN logo
Friday, July 8, 2016

One of Theo Epstein's most admirable traits as a baseball executive is his willingness to surround himself with intelligent, motivated people and push them to be better, as they simultaneously challenge him. This collaborative partnership is readily apparent during the June first-year player draft, when Epstein bunkers in with the Chicago Cubs' scouting contingent over takeout sandwiches and spirited debate.

"He's not one of these general managers or presidents of baseball operations who sits there for an hour and listens to the top two round guys and then leaves,'' said Jason McLeod, who has worked for Epstein in Boston and Chicago. "He's there every minute of every single day, the entire time we're in the war room.

"We'll be talking about college senior filler guys in the 15th round, and Theo's asking, 'Why are we putting him here?' There are times when I'm like, 'Theo, you have way more important things to worry about than this guy we're filling out our short-season team with.' It goes back to him being driven to make the best decisions at all levels of the organization. He's going to challenge you on why you're recommending a certain move, or why you want a pitcher in A-ball to throw a slider over a curve. He's completely invested in the health of the organization at all levels.''

Epstein's attention to detail was rewarded this week when the MLB All-Star rosters featured a deluge of names and faces from his 14-year tenure with the Red Sox and the Cubs. He acquired 11 members of the 2016 National and American League squads through the draft, free agency, the international signing market and trades. David Ortiz is the senior citizen of the group at 40, while Addison Russell is the resident pup at 22. And if Dustin Pedroia can make it to San Diego through the final-vote process, he'll make it 12.

It's human nature for Epstein to feel a sense of gratification over such a momentous haul. But as the praise rains down upon him, he has the borderline sheepish sensation of a guy accepting an Academy Award on behalf of everyone else who deserves a chunk of the statuette.

"It's the player's accomplishment, and you're first and foremost just proud of and happy for the player,'' Epstein said in an email. "That said, it's always a gratifying moment for the whole organization when a player's talent and hard work are rewarded with an All-Star selection, particularly for a young or homegrown player.

"This whole industry is about group effort. Every draft pick, trade, or signing is a product of countless people working together to make it happen. We've been so fortunate to have great groups in both places.''

Some of Epstein's acquisitions were obviously more impressive than others. Jon Lester was a three-time All-Star when the Cubs signed him to a $155 million contract in December 2014. Epstein and Cubs general manager Jed Hoyer knew they were getting the consummate pro many other teams coveted when they signed Ben Zobrist as a free agent last winter, and the Cubs were fortunate to bring back Dexter Fowler on a one-year, guaranteed $13 million contract in February after a three-year deal with the Baltimore Orioles fell through.

Conversely, the acquisition of Jake Arrieta from Baltimore will go down as an all-time heist. The Cubs also struck gold when they acquired Russell in a trade with Oakland, but he was available only because Billy Beane and the A's were going all-in in the pursuit of a playoff berth. Epstein, in hindsight, has said he would have made a similar move if he were in the same position.

Given the fickle nature of the draft and international signings, the process of watching a teenager develop into an All-Star lies at the heart of what Epstein and MLB talent evaluators hold dear. Here's a look back at five of Epstein's 2016 All-Stars, and some "Eureka!" moments that convinced Epstein and other people in the war room that they might have hit pay dirt.

Xander Bogaerts

Craig Shipley, then Boston's international scouting director, and scout Mike Lord had just checked out a 16-year-old Aruban infielder named Jair Bogaerts in 2009 when Jair shared an interesting tidbit: His twin brother, Xander, was home with the chicken pox and might be worth a look too.

Shortly thereafter, the Red Sox worked out Xander and signed him to a $410,000 bonus. He was hailed as the franchise's most acclaimed international signing since Hanley Ramirez when the Sox invited him to their spring complex in Fort Myers, Florida, where a lot of uniformed personnel were interested in seeing if he was worth the investment.

"Torey Lovullo was our Triple-A manager at the time, and we were out on the field watching Bogey take batting practice,'' said Red Sox general manager Mike Hazen, who was then player development director under Epstein. "I remember Torey looking at me like, 'Who is this guy?' Even at that young age, Xander stood out on the field. His physical presence and the strength in his swing stood out even when he was that young.''

Mookie Betts

How on earth did Betts, a super athlete who has made the transition from second base to All-Star outfielder in the majors, last until the 172nd pick in the 2009 draft?

The Red Sox began monitoring Betts closely the summer before his senior high school season in Nashville, and they loved his athleticism. Betts was relatively small in stature, and talent evaluators had reason to wonder if he would ever hit with much power. But Danny Watkins, Boston's area scout, was an early advocate for Betts, and when respected evaluators Tom Allison, Mike Rikard and Mark Wasinger added their endorsements, the Red Sox were hooked. They gave Betts a $750,000 bonus to dissuade him from accepting a baseball scholarship to Tennessee.

"When we got Mookie in the system, the thing that jumped out was his power,'' Hazen said. "He led our minor leagues in slugging for a couple of years -- out of nowhere. And every day and every year you watched him play, he kept getting better and better and better.

"I think that was one of the best pure scouting jobs we've had here, in terms of identifying makeup and athleticism and bat speed and the ability to hit. Those four guys [Watkins, Allison, Rikard and Wasinger] were the ones that really did all the heavy lifting on it.''

Jackie Bradley Jr.

The Red Sox had the 19th, 26th, 36th and 40th picks in the 2011 draft. But after Bradley tore it up as a sophomore and won the College World Series Most Outstanding Player award at South Carolina, it appeared unlikely he would still be available when it was their turn to pick. Quincy Boyd, Boston's area scout, had plenty of company as a Bradley booster.

"Theo and I had a quick conversation in January, as we always do,'' said Amiel Sawdaye, then Boston's amateur scouting director. "I would say, 'Here are the guys we like going into the year.' Jackie's name came up, and I remember Theo saying something like, 'There's no chance he'll be around, is there?'"

The story took an unexpected twist when Bradley's stock fell after he suffered a wrist injury and slumped to .259 as a junior. Bradley was still on the board after Boston selected Matt Barnes, Blake Swihart and Henry Owens with its first three choices, and the Red Sox took the plunge at No. 40. Five years later, after some pronounced struggles at the plate, Bradley is tied for fourth among MLB outfielders at 3.5 wins above replacement and is bound for his first All-Star Game.

Boston's 2011 draft haul of Bradley, Betts, Travis Shaw and Swihart is about as good as it gets. But Sawdaye, in the mold of Epstein, understands the hazards of basking in too much industry praise.

"You can sit here and pat yourself on the back for the successes,'' Sawdaye said, ''but the ones that really kill you are the ones you missed on. People say, 'Oh, great pick on Jackie, or Mookie.' In the back of my mind, all I think about is the guy that we should have taken the year before, and I look back now and kick myself because we didn't.''

Kris Bryant

The Cubs' had the second pick in the 2013 draft, and it was going to boil down to Bryant or pitchers Mark Appel or Jonathan Gray. After the Houston Astros chose Appel at No. 1, Cubs scouting director Jaron Madison made the call for Bryant.

Area scout Alex Lontayo had done extensive legwork on Bryant at the University of San Diego. The Cubs watched Bryant swing a wood bat on the Cape Cod League, and they were comfortable with his makeup through the rave reviews he elicited from his college coach, Rich Hill.

The clincher came about two weeks before the draft during the West Coast Conference tournament, when Epstein, Hoyer and McLeod sat down for a conversation with Bryant in a Stockton, California, hotel lobby. They came away convinced he fit the profile.

"As we left that meeting all three of us were like, 'Wow, if there's a guy who could step into Chicago as a No. 2 overall pick and deal with the expectations heaped upon that selection, it's this guy, with the way he's wired and he handles himself,''' McLeod said. "Three years later, he's been everything we thought he would be. Kris does a great job separating -- whether it's offense from defense, or his life on and off the field. He just doesn't seem to get rattled by much. He's a young man who knows who he is, and he's comfortable with that.''

Anthony Rizzo

For years, it was generally assumed that young players might have difficulty adjusting to pressure-packed environs in a big market, but six of Epstein's All-Stars have turned that bit of conventional wisdom sideways. Bogaerts, Bradley, Betts, Rizzo, Bryant and Russell have all emerged as world-beaters in Boston and in Chicago in the 22- to 26-year-old age spectrum.

Rizzo, chosen in the sixth round of the 2007 draft on the recommendation of Red Sox scout Laz Gutierrez, surmounted numerous hurdles on his way to stardom.

He underwent six months of chemotherapy after being diagnosed with Hodgkin lymphoma before being declared cancer-free at age 19. He was 21 when Epstein sent him to San Diego in a trade for Adrian Gonzalez, and 22 when Epstein and Hoyer brought him to Chicago in a trade for Andrew Cashner. The only thing left for Rizzo at that point was to remake his swing and prove he could hit a big league fastball.

Now that Rizzo is appearing in his third straight All-Star Game -- with six fellow Cubs -- it's clear the zigs and zags were worth it. "It hasn't been a straight, linear upward path for Anthony,'' McLeod said. "He's had to deal with expectations and a lot of outside forces, but he's just continued to go out and play baseball. He gets along with everybody. When you see his parents, you understand why that is.''

When John and Laurie Rizzo watch their son tip his cap to the crowd Tuesday night at Petco Park, they'll be joined by an area scout who believed in Anthony Rizzo, national cross-checkers who signed off on him, a scouting director who had the conviction to call his name on draft day, and an array of trainers, clubhouse attendants, coaches, managers and other support personnel who've left an enduring mark on his development.

Epstein will be watching the ceremonies with a sense of pride too. As he knows from experience, it takes a village to raise an All-Star.

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