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The Cubs were one 2014 loss to the Red Sox from drafting Andrew Benintendi in 2015

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The Red Sox star could have been playing on the North Side.

John Glaser-USA TODAY Sports

Tracking the MLB draft is a mindset. It’s a draft that few bother with. After all, it’s fraught with guessing wrong, and having to wait. The catcher (Steve Chilcott) drafted before Reggie Jackson in 1966 was a perfectly valid and accepted alternate. Chilcott could have been a very good player in his own right, but for an injury to his throwing arm. Playing if/then gets very tenuous regarding the baseball draft. However, if everything else had played out the same in 2014, the Cubs were one loss from drafting Andrew Benintendi.

By different measures, the Cubs use very similar player assessments to the Red Sox and Cardinals, my tracking has shown. For instance, the Cubs were apparently very “in” on Jack Flaherty. A very respected prep arm, Flaherty had “makeup numbers” that were off the charts. The Cubs considered Flaherty a reasonable gamble as he was coming off the board, chatter had it.

The Cubs had selected Kyle Schwarber with their first choice (fourth overall) in 2014. With a first-round supplementary choice, the Cardinals selected Flaherty from Harvard-Westlake High School in Los Angeles. (At one time, they had Flaherty, Max Fried, and Lucas Giolito on their roster at the same time. Good luck hitting that.) Shortly after Flaherty was selected, the Cubs selected Jake Stinnett from the University Of Maryland.

Both the Cubs and Cardinals selected Daniel Poncedeleon (the Cubs in 2013, the Cardinals a year later). I seem to remember a few others recently that were high on both teams’ lists. The Cubs and Cardinals are kin when it comes to assessing off-field aspects of the draft. With the Cardinals drafting a bit before the Cubs in 2019, St. Louis figures to steal more than a few names, and we’ll likely never know about it.

It’s a bit more hazy tracking anything between the Cubs and Red Sox by rumor and innuendo. However, as the decision-makers in the two organizations seem a bit cross-pollenated, projections seem reasonable. The Cubs and Sox both want hitters who know the strike zone, play a three-way game (offense/defense/base running), and help lead to wins in similar ways. During the run-up to the 2015 draft, Benintendi was likely to slip to the Red Sox spot at seven. He was unlikely to reach the Cubs at nine. Not because of the White Sox, at eight.

At the end of June 2014, the Cubs traveled to Fenway Park for a three-game series. The Cubs swept the Red Sox, a highlight of their 73-89 season, including a near no-hitter from Jake Arrieta, perhaps a precursor to the two he did throw. The Red Sox finished the 2014 campaign with a 71-91 record. The White Sox closed at 73-89, as did the Cubs, for the odd tie between the two. The White Sox drafted before the Cubs every round on the tiebreaker: the team with the worse record in 2013. (The White Sox had won 63, and the Cubs 66, in 2013. Hence the White Sox chose first.)

If the Red Sox had defeated the Cubs once in that series, and everything else had played out the same, the White Sox (73) would have selected ninth, and the Red Sox and Cubs would have tied at 72 wins. The Cubs would have won the tiebreaker (Boston had won 97 in 2013), and selected seventh, with Boston sliding to eighth.

As everything played out through the college season, the Cubs would have selected Benintendi, who had a breakout campaign in 2015 as an outfielder for the Arkansas Razorbacks. A look back at that not-so-distant process is an interesting study in how the choosing process has changed in a rather short period of time. College players and hitters, seem more preferred early, now.

People seem to really dig “re-drafts” now. They sometimes prefer re-drafts to actual drafts, as the redrafts pay far more attention to pro games than college ones. Which, conversely, is why I like to slice open the proverbial baseball to assess why people did what they did, when they did it.

Dansby Swanson and Alex Bregman were the first two players selected in the 2015 draft. Swanson, on the strength of being a true shortstop, was considered the logical first choice. If the Diamondbacks (who would later send Swanson to the Braves in the Shelby Miller trade) had figured Bregman would be as good as he was, they’d have flipped it. However, you only have the information available at the time.

Brendan Rodgers was a hyped prep shortstop, and that he was selected third was about a foregone conclusion. Rodgers had an OPS of .790 in 2018 in the upper-minors. He could still be a very useful asset for the Rockies in the not-too-distant future. Whether you think so or not, Rodgers was the consensus call at three.

Next up came Dillon Tate, a 6-2 right-handed pitcher from California-Santa Barbara. Every MLB draft process has a helium arm. Tate was it in 2015. His velocity was mid-to-high 90’s, and his college WHIP as a junior was 0.91, with 111 strikeouts in 103 innings. If you wanted an ace in this draft, Tate was the guy to leap for, and Texas did. As a professional, he’s gone from Texas to the Yankees, then the Orioles. He made 22 starts in Double-A in 2018. Perceived aces, don’t always.

Fifth off the board was Houston’s selection of outfielder Kyle Tucker. I’m as clueless as you are regarding prep selections. This seemed an acceptable choice at the time. My primary memories of Tucker were that he played rather well against Myrtle Beach in the Carolina League in 2017. I’ll defer to you on the present wisdom of the selection.

Lemont, Illinois’ Tyler Jay went sixth to the Twins. Primarily the closer for a sensational Illinois team, he only started two games for the 2015 Super Regional hosts. (They would lose to Swanson’s Vanderbilt squad. Carson Fulmer and Kyle Wright pitched for Vandy.) The 6-1 left-hander marched up draft boards with a mid-90s fastball, and a repertoire to boot. His slider and change were both swing-and-miss offerings. His WHIP was a comical 0.70.

In 2016, Jay started 15 games on the mound as a Twins farmhand. Since then, he’s pitched in a total of 70 innings, mostly in relief. His WHIP in 2018 in the Tennessee Smokies’ Southern League was 1.58. Caveat emptor.

Benintendi, from Cincinnati, burst onto the college scene as a sophomore-eligible for the Arkansas Razorbacks, vaulting from one homer to 20. His OPS for the SEC Hogs was a nearly unfathomable 1.205. The only “concern” on Benintendi was whether his season was a one-off. It wasn’t.

The White Sox went with Fulmer, and the Cubs selected Ian Happ. The draft assessors were good with the top nine picks as they were, at the time. The next four choices were preps. The closest to MLB is Tampa’s Forrest Whitley, a pitcher. Walker Buehler went 24th to the Dodgers (from Vanderbilt, off a shaky season). The Cubs’ selection in the next round was Donnie Dewees, an outfielder later sent to Kansas City in the trade for Alec Mills.

The one game that the Cubs didn’t lose in Boston was the difference between the Cubs having Ian Happ and Andrew Benintendi. Had the Red Sox won one of those three games, it’s very likely the Cubs would have selected Benintendi. How things would have played out from there are up for argument. However, it seems the Cubs would have drafted Benintendi, given the chance. They didn’t get the chance.

Looking at draft classes after the fact for me are as much about “why” who was selected, as who was selected. The temptation to leap for a potential ace is very tempting. As a fan, if that’s the way you want to go with regularity, that’s cool. However, with any pitcher, quite a few things can go wrong, and often will.

I strongly encourage thought and discussion on upcoming draft classes. To adapt a line of President John F. Kennedy’s, not because it’s easy, but because it’s hard. Talking about the draft in advance is fraught with mistakes. That’s a given. However, until you learn a lesson, you’re unlikely to follow it.

This wasn’t written to say “the Cubs should have tanked a game.” It’s a look back at a draft class to try to figure who chose which players, for which reasons. The Red Sox will have Benintendi for a few more years cost-controlled. The only reasonable selection that the Cubs could have made that was better than Happ was to take Buehler, who was much weaker as a junior at Vanderbilt than as a sophomore. I don’t remember any Cubs fans pressing for the next Dodgers ace in that case.

Congratulations to the Red Sox (Benintendi) on the 2018 American League pennant, and the Dodgers (Buehler). I would have preferred the Astros, but both sides were worthy. And, no. I don’t remember any clarion calls for Benintendi over Tucker. Draft choices are long-term cost-controlled assets. Hit on those, and you’ll be good for awhile.