White Sox should aggressively pursue Justin Upton

The Chicago White Sox have a decision to make, and per ESPN’s Doug Padilla, they haven’t quite made it yet.

"“’Since the end of the season, Rick has had a number of conversations with [chairman] Jerry [Reinsdorf] and I and we have bandied about a number of scenarios: Plan A, Plan B, Plan C,’ executive vice president Kenny Williams said. ‘A lot of it depends on what’s available to you.’‘But as far as a plan of attack right now, if I went to him and said ‘OK, I want your definitive plan heading into the winter meetings,’ he [Hahn] couldn’t give it to me.'”"

The whole idea that on November 22nd, a mere two weeks before the Winter Meetings in Nashville, Rick Hahn is throwing darts at three disparate plans hoping for insight is ludicrous. I buy that this process was happening in late September, but after the GM meetings the landscape should be much clearer.

They know who is available. Look no further than Jason Heyward, Justin Upton, Yoenis Cespedes, Ian Desmond, Ben Zobrist, and Jordan Zimmerman; all players who could fill a need on the 2016 club.

On the trade route, buzz has surrounded names like Tyson Ross, Carlos Gonzalez, and Todd Frazier; also ideal targets for the White Sox.

It may be a fluid situation, and it’s true that the market evolves and follows a sort of domino effect that opens and closes various opportunities, but this is more a diversion than anything else. It’s an attempt to use the media as a pawn to gain leverage in trade talks and free agent pursuits, and make the competition downright confused as to what your game plan is.

I for one, will have no part in their ruse.

The White Sox have a direction, and it’s safe to assume that “Plan A” is going to be a bona-fide postseason push that expands payroll, while “Plan B” is more of the same in the event that Reinsdorf remains stubborn about preserving a comfortable bottom line, while “Plan C” is Hahn’s response to such a penchant for mediocrity.

“Plan C” would likely be Hahn opting out of the “Plan B” of signing David Freese and a cost-effective backend starter in favor of a full-scale rebuild that could even see Chris Sale leave town.

This article assumes that Jerry Reinsdorf read my piece about the White Sox needing to expand payroll, and is in the “Plan A” camp. If that’s the case, then the White Sox should be falling head over cleats for outfielder Justin Upton.

Upton was the number one overall pick in the 2005 amateur draft. Taken by the Arizona Diamondbacks, Upton was a five-tool standout destined for superstardom.

Making his big league debut at the tender age of 19, Upton’s career has been somewhat of a mixed bag.

The White Sox should be falling head over cleats for outfielder Justin Upton.

By no means has he been a bust, but considering the lofty ceiling that preceded his career, he’s fit the bill of a player that’s always seemed to have that untapped potential.

Over nine seasons, he has a career .271/.352/.473 (.825 OPS) slash line with 190 home runs. He’s a three-time All-Star and his best season was in 2011, when he finished 4th in MVP voting with a .289/.369/.529 line to go along with 31 bombs and 21 stolen bases, and a 6.1 WAR, per Baseball Reference.

That’s the type of production Upton should be good for on an annual basis, but he hasn’t been able to sustain that level of success. Still, he’s never had a poor season and seemed to find a more consistent power stroke over the last three years, averaging 25 home runs a season over that time.

His 2015 was encouraging. Despite playing half of his games in pitcher friendly Petco Park, he managed a .790 OPS with 26 home runs and 19 stolen bases.

He actually hit worse away from Petco, which is really just an anomaly more than anything else. In other words, he should do very well if placed in a hitter’s park.

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What’s interesting about Upton, is that he’s really a boom or bust type of player over the course of a season. Just look at last year as an example. He was dominant in May, posting a .343/.418/.536 line, but followed that up with a poor June (.608 OPS) and even worse July (.551 OPS).

He rebounded in August (.923 OPS) and was average for the rest of the season.

It’s not rare for Upton to disappear during stretches and it usually does occur early in the Summer leading up to the All-Star Break, but when he’s on, he’s on.

Upton can carry a line up when’s he hot, and it’s almost overwhelming to imagine what a hot Upton paired with Jose Abreu would look like.

There are inherent pros and cons that come with Upton. His aforementioned streakiness is an obvious con, but he also has fairly even splits, so he’s not destined to become a platoon player anytime soon.

If we’re comparing Upton to Cespedes, they’re ultimately a wash. Upton has age on his side (28 compared to Cespedes’ 30) but also comes along with a qualifying offer, while Cespedes doesn’t.

I think buying one’s prime years in free agency should trump surrendering the comp pick. The White Sox also know what Cespedes is. He’s a potent bat, but his standout 2015 is really his ceiling. He was a 6.3 WAR player last year, and that is certainly worth the big bucks but may not be replicable.

With a contract that could take him into his mid thirties, it’s hard to imagine he’ll consistently match his 2015 production, especially on the backend of that deal.

In contrast, Upton is still on a stepping stool and swiping his hands at a higher ceiling. The first three years of his next deal will occur during his age 28-30 seasons, historically right in a typical ballplayer’s prime.

Even at an already high cost, there’s potential surplus value if it all clicks for Upton in Chicago. It’s not hard to imagine him being close to a 30-30 player, and if he really caught fire, a 40 home run season playing in a hitter’s park like U.S. Cellular field wouldn’t be out of the question.

Upton’s defense in right would also be an upgrade over Avisail Garcia as his athleticism made him a Gold Glove finalist in 2014 and 2015. He isn’t Jason Heyward or Yoenis Cespedes but the glove has a floor of competence.

The biggest red flag with Upton are the strikeouts. He’s amassed 150 Ks in each of his last three seasons, and had a 25.6% strikeout rate in ’15, which is just a touch above his career average.

It’s not that Upton’s plate discipline is necessarily bad, as he swung at less out of zone pitches than the average hitter, per FanGraphs. Although, his o-contact was below average when he did hack at balls off the plate.

But all of this is to be expected with a power hitter, and whiffs are merely a trade-off of being a power threat every at bat.

While the White Sox haven’t had the best track record recently with strikeout/home run players (Adam Dunn, Adam LaRoche, Dayan Viciedo, etc.), Upton’s .203 ISO in 2015 would have looked awfully nice on a power starved Chicago roster.

There is value in being able to hit to all fields, and Upton’s spray chart is fairly balanced but what he brings to the table is true right-handed pull power, which the White Sox are desperately lacking.

Jose Abreu and Trayce Thompson showed an ability to deposit a fastball into the left field seats, but outside of them, this is a skill-set that isn’t really anywhere else on the roster.

Upton also provides Robin Ventura with some flexibility as far as line up construction goes. At the moment, Melky Cabrera is the only viable hitter to protect Jose Abreu, and that’s not saying much. Adding Upton and hitting him fourth, would give Abreu the first dose of real protection he’s ever seen on the South Side.

Allowing the 2014 MVP candidate to see more fastballs is always a plus. If Ventura chooses to flip the two, and place Abreu behind Upton, then Upton will get the lion’s share of pitches in the zone. That’s the advantage of having two centerpiece bats in a line up, which the White Sox haven’t had for some time.

Of course, a player like Upton isn’t found at your wholesale Costco. Try your local Whole Foods. Justin Upton’s agent, Larry Reynolds, will do his best to get his client a mega-deal. In fact, an opt-out clause that let’s Upton see free agency again in his early thirties could also be on the table.

MLBTraderumors’ columnist Tim Dierkes, has Upton pegged at a seven-year, $147 million contract.

ESPN’s Jim Bowden, predicts a slightly higher average annual value and has him slated to land a seven-year, $161 million deal. Bowden also explicitly lists the White Sox among a few other teams as a “best fit” for the outfielder.

Seven years seems reasonable to me as the deal would expire after Upton’s age 35 season. About $22 million a year for Upton’s services is really just the going rate these days. Hey, the qualifying offer is already at $16 million, why shouldn’t an All-Star cost roughly 50 percent more than that.

The White Sox’s largest contract in franchise history was given to Jose Abreu in the form of a 6-year, $68 million deal. It is unprecedented for a big market or even median market team to not have passed the $100 million barrier by now. In fact, about more than 80 percent of the league already has.

I think $154 million over seven years brings Upton to the South Side. The White Sox can sell him on being a big piece in a legitimate contention window and playing for a team that also features Jose Abreu and Chris Sale.

Signing Upton would enable the White Sox to move Cabrera to DH and open up the door to using either Avisail Garcia or Trayce Thompson as a pot sweetener in a deal for a big-time third baseman.

The basic point is this: The White Sox need more power, more credibility, more speed, and better defense. Justin Upton brings all of that in one package. The only caveat, it’s for a cool $150 million. Time to open up the checkbook Jerry.

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