Jason McLeod goes inside the Ian Happ/Andrew Benintendi draft

Jason McLeod goes inside the Ian Happ/Andrew Benintendi draft

Imagine Andrew Benintendi — “Freddy Lynn reincarnated” in Joe Maddon’s mind — flying all over Wrigley Field and hitting in a lineup that already included Kyle Schwarber, Kris Bryant, Anthony Rizzo and Addison Russell all under club control through the 2021 season.

Two names stood out at the top of the draft board on June 8, 2015, the Cubs targeting their favorite demographic — college hitters — with the ninth overall pick: Benintendi and Ian Happ.

A Boston Red Sox scouting department with deep connections to Theo Epstein and Jason McLeod came at the No. 7 pick with a similar philosophy. Where one fast-track player hit .295 in 34 games for a 93-win team last year — and entered this season as Baseball America’s No. 1 overall prospect — the other is now batting cleanup for the defending World Series champs.

“We obviously liked (Benintendi) quite a bit,” McLeod said on this week’s Cubs Talk Podcast. “We spent a lot of time scouting him as well. Again, going back to that question, did we think (Ian would) be here this fast? (Look at) what (Benintendi’s) done with Boston. Players have recently just kind of switched the timetable a little bit, especially those ultra-talented guys.”

McLeod, the senior vice president who oversees scouting and player development, couldn’t have his staff zero in on one player, the way the Cubs focused so heavily on Bryant (No. 2 overall) and Schwarber (No. 4 overall) in the 2013 and 2014 drafts.

One theory floating around an organization already loaded with hitters wondered if the Cubs would roll the dice with Brady Aiken, who got drafted with the first selection in 2014 but couldn’t reach an agreement with the Houston Astros amid medical concerns.

The Cubs ultimately viewed that as a risky investment where the payoff would maybe take years. Aiken — who had been recovering from Tommy John surgery on his left elbow — got drafted by the Cleveland Indians eight spots after Happ and is now pitching in A-ball.

Instead of dreaming about potential, the Cubs felt far more comfortable projecting Happ’s high-level performance at the University of Cincinnati and as a two-time Cape Cod League All Star. The Cubs would keep collecting young hitters and getting solid returns, knowing that some could be traded for pitching later.

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That draft order would’ve been switched around if the Cubs hadn’t swept a three-game series from the Red Sox in the middle of the 2014 season, as a Boston Globe story detailed during last month’s potential World Series preview. The rebuilding Cubs (73-89) actually finished with a better record than the defending World Series champs (71-91) that year.

“Everything just aligned,” McLeod said. “Obviously, the Red Sox made it easier for us when they took Benintendi with their selection. We had a pretty good sense once that happened that Happ would be our guy.

“I can tell you that once Andrew was taken, those of us in the room felt really good, like: ‘We’re going to get Happ.’ Once he was there for us, we were all excited to bring in this switch-hitter with power and on-base (skills) who was another kind of blue-collar, hard-nosed guy.

“He’s very intense. He has high expectations of himself. We’ve seen that. He’s quieter in the sense that he’s not rah-rah. He’s just very intense about what he wants to get accomplished when he gets to the ballpark that day.”

Happ clearly didn’t spend a lot of time in the minors — 227 games overall and only 26 on the Triple-A level — but he had a sense of purpose and a chip on his shoulder while working on his defense.

“There were questions,” McLeod said. “Not on if he could play defense. I think the conversation with him coming out of the draft that year was: What is his best position? Because he had played infield, he had played outfield. Where would the eventual landing spot be?

“It was more in a positive way. Not: Well, gosh, where can we hide him on the field? It was never anything to do with that. (But) I do feel like he can be an average second baseman in the major leagues. He has enough athleticism, for sure, to be an average outfielder at multiple positions in the outfield.”

Between the home runs, the sliding catches in the outfield and the way he handles himself in the clubhouse, Happ keeps giving the Cubs reasons to not send him back to Iowa. Maddon is already talking up Happ as a Bryant defensive clone and imagining the possibilities.

“I wouldn’t put it past him,” McLeod said, “if Joe asks (Ian to do what) he does with Kris. I think that Ian would be able to be a player like that who could go play first base, who could go stand at third, catch what’s hit to him. If you were asking me to pigeonhole him in one spot, I don’t know exactly what that spot is yet, just because he’s been playing a lot of different positions. I think he can be a big-league defender at multiple positions.”

Jake Arrieta getting close and message to Cubs is clear: ‘We can’t expect outside help to get us out of this rut’

Jake Arrieta getting close and message to Cubs is clear: ‘We can’t expect outside help to get us out of this rut’

MIAMI – Kyle Schwarber’s offensive spiral had gone on for so long and gotten so deep that the shock value of sending a potential franchise player to Triple-A quickly wore off once the news broke on Twitter.

The Cubs sent their message directly to Schwarber. Even if the bosses wanted to, the Cubs couldn’t put the rest of the clubhouse on edge by demoting a .171 hitter with 260-plus plate appearances in late June. 
 
The Cubs are in survival mode, not a position to play mind tricks, beginning an 11-games-in-11-days road trip with World Series MVP Ben Zobrist (left wrist inflammation), Gold Glove outfielder Jason Heyward (left hand abrasion) and Cy Young Award finalist Kyle Hendricks (right hand tendinitis) all on the disabled list.   

Whether or not the big trade for a frontline pitcher happens, there are still five-plus weeks left until teams feel the urgency of a deadline.   

“If something presents itself that makes sense, we’ll certainly jump on it,” general manager Jed Hoyer said over the phone before an 11-1 win at Marlins Park. “But to us, the answers are in that clubhouse. We can’t expect outside help to get us out of this rut. The answers are in there, and we believe in those guys. 

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“Will we be active? No question. But that’s not going to happen for a while and there’s a lot of games to be played between now and July 31.”  

The Cubs (37-35) aren’t booking Schwarber’s trip to Iowa so he can be converted into a pitcher. An aging, stressed rotation remains a much bigger concern than the boom-and-bust periods with a young offense. 

Kris Bryant unleashed an MVP swing when he launched a three-run homer into the left-center field patio deck. All-Star shortstop Addison Russell just missed hitting for the cycle while rookie Ian Happ (this year’s Schwarber) also went 4-for-5. Young catcher Willson Contreras blasted his seventh home run.

More importantly, Jake Arrieta looked more like himself, limiting the Marlins to one run across seven innings.

“Interesting, isn’t it?” manager Joe Maddon said. “The biggest thing for us to really do well is to pitch well, because you can’t anticipate scoring a ton of runs without this group involved. You shouldn’t. That’s a bad assumption on my part. So you probably have to take more chances defensively. Your pitching staff – you really got to try to draw out of them as much as you possibly can.”  

Did Cubs start the tailspin by making Kyle Schwarber their leadoff guy?

Did Cubs start the tailspin by making Kyle Schwarber their leadoff guy?

MIAMI – Everything aligned for the Cubs to make Kyle Schwarber their leadoff hitter. Joe Maddon’s gut instincts told him to do it – so the manager asked the Geek Department to run the numbers – and the projections backed him up. A front office raised on Bill James principles endorsed the idea after Dexter Fowler took an offer he couldn’t refuse – five years and $82.5 million – from the St. Louis Cardinals.
   
It all looked good on paper and sounded reasonable in theory. But by the time the Cubs made the Schwarber-to-Iowa move official before Thursday’s game at Marlins Park, the slugger once compared to Babe Ruth in a pre-draft scouting report had devolved into the qualified hitter with the lowest batting average in the majors (.171) and an .OPS 75 points below the league average.  

If Schwarber had been batting, say, sixth since Opening Day, would the Cubs be in a different spot right now?   

“Obviously, I can’t answer that,” general manager Jed Hoyer said. “It’s an impossible question to answer. We put him in a leadoff position and he struggled. We obviously moved him out of that position (and) that didn’t work either. I know that’s what people are going to point to, because that’s a variable in his career. 

“Obviously, hitting him leadoff in 2017 didn’t work. Whether or not it caused the tailspin, I have no way to answer that question.”   

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The Cubs also deserve credit for: drafting Schwarber when the industry viewed him as a reach with the No. 4 overall pick in 2014; fast-tracking his development to the point where he could help the 2015 team win 97 games and two playoff rounds; and overseeing a rehab process that allowed him to be a World Series designated hitter less than seven months after reconstructive surgery on his left knee.    
 
The Cubs will have their hitting instructors give Schwarber subtle suggestions, focusing on how he starts his swing and where he finishes, trying to reestablish his balance and confidence during this Triple-A timeout.
    
But deep down, this is a 24-year-old player who never experienced a full season in the big leagues before and wanted so bad to be a huge part of The Cubs Way.

“I do think a lot of the problems are mental,” Hoyer said. “These struggles have kind of beaten him up a little bit. Like anyone would, he’s lost a little bit of his swagger, and I think he needs to get that back. But I think when you look at what a great fastball hitter he’s been – how good he was in ’15, how good he was last year in the World Series – the fact that he hasn’t been pounding fastballs this year is a mechanical/physical issue that we’ll be looking to tweak. 

“This is a guy that has always murdered fastballs and he’s not there right now.”