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Making A Cubs Midsummer Deal: San Diego Padres

The Padres are nearing the time to sell on a whole boatload of pieces.

Tim Heitman-USA TODAY Sports

It's no secret that the San Diego Padres were the darlings of the offseason. Over a two-day stretch in December 2014, the Padres made more moves than many of us could ever imagine a team making in an entire year. They acquired starting catcher Derek Norris, outfielder Wil Myers, and third baseman Will Middlebrooks at the cost of the depth in their farm system, including righty Joe Ross, righty Jesse Hahn, reliever R.J. Alvarez, and, famously, shortstop Trea Turner, who lived in limbo for six months while he waited to be trade-eligible following his first year from signing. To Padres general manager A.J. Preller's credit, he managed to acquire the above trio without dealing from the top of his prospect list, depending on your opinion of Turner.

Unfortunately for the Padres, they made another fateful move on the same day as the Norris trade, inexplicably sending emerging catcher Yasmani Grandal and pitching prospects Joe Wieland and Zach Elfin to the Dodgers for broken-down, immobile former slugger Matt Kemp.

But that wasn't all. They also traded former seventh overall pick lefty Max Fried and a trio of moderately interesting prospects for the final year of team control of Justin Upton.


Preller took almost two months off, but he then dipped into his remaining payroll space to take a stab at forming a top rotation, signing Royals playoff hero James Shields to a heavily backloaded four-year, $75 million deal. Rumors had the Cubs bowing out when the bidding exceed three years and $60 million.

Apparently Preller felt anxious by the time the season rolled around, so on Opening Night, he sent his top pitching prospect, near-MLB arm Matt Wisler, along with second rounder Jordan Paroubeck, scuffling outfielder Cameron Maybin, a competitive balance Round A pick, and the last year of Carlos Quentin's dead weight salary to the Braves for the three final years of B.J. Upton (who now goes as Melvin Upton, Jr.) and ace closer Craig Kimbrel.

State of the Franchise
There's no denying that, on the whole, the moves gutted a big chunk of the San Diego farm system. Even with the above transactions, Preller kept four of his top five prospects in catcher Austin Hedges and outfield trio Hunter Renfroe, Rymer Liriano, and Michael Gettys.

Nevertheless, the offseason splurge was clearly intent on building a 2015 winner, and the early returns looked promising as the club jumped out to a 10-5 start. The team quickly fell to .500 thereafter but hung at or around the .500 mark until mid-June. From a 32-32 record on June 13th, the Padres have struggled mightily in falling to 41-49 at the All-Star break, 7.5 games behind the Cubs for the second wild card position.

To make matters much worse, Kemp has been horrendous as expected, Jedd Gyorko is in danger of leaving the Majors for good, Myers predictably flopped as a centerfielder and will miss months with continuing wrist injuries, Middlebrooks is carrying a .242 on-base percentage at midseason, contract-year righty Ian Kennedy imploded, and Shields got bit by the homer bug for the first time in five years despite moving to the National League and the confines of PETCO Park. The season is going up in flames.

To make matters worse, the cupboard is relatively thin in the minor leagues, and the Padres have massive outstanding payroll commitments after this season including the following:

Kemp: $72 million through 2019
Shields: $65 million through 2018 (includes 2019 buyout)
Gyorko: $33 million through 2019 (includes 2020 buyout)
Melvin Upton, Jr.: $31.9 million through 2017
Kimbrel: $25 million through 2017 (includes 2018 buyout)
Corey Luebke: $1.75 million (2016 buyout)
Joaquin Benoit: $1.5 million (2016 buyout)

Yikes. In addition to that septet, emerging two-pitch righty Tyson Ross figures to command somewhere in upwards of $20 million over his two remaining seasons of arbitration eligibility. Especially for a small market team, the Padres have a lot of money committed without having received much return on their investment.

Trade Assets
At this point, Kemp is essentially unmovable unless Preller is willing/able to eat significant cash and/or willing to deal attractive assets in order to move on from his albatross contract. Gyorko is in the same boat. Ditto Luebke, though his remaining commitment is minimal.

That leaves Benoit, Kimbrel, Upton Jr., and Shields among the future-committed tradable pieces. I don't think that the Padres will move Kimbrel and Benoit isn't a great fit for the Cubs. Further, Melvin Upton Jr. doesn't add much to the current Cubs roster. Obviously the foregoing ignores three of San Diego's most attractive assets: impending free agent bopper Justin Upton, fellow impending free agent everyman Will Venable, and perennially injured starter Andrew Cashner. It's possible that the front office could target Cashner, but having already traded him away once, that would be a surprising move and Cashner's next injury is practically inevitable. I suspect that Preller is unwilling to sell low on Cashner with additional club control remaining, so this doesn't seem like a match.

While we could discuss the entire roster, any Cubs interest on current Padres figures to focus on Shields, Justin Upton, and Venable, so we'll only look at that trio the rest of the way.

Except that I don't think Justin Upton is a likely Cubs target. Upton will still attract interest based on his pedigree -- he's a former number one overall pick he is still just 27, has a prototype build, and has produced consistently strong seasons for years including four seasons of at least 25 home runs -- but his actual production has been terribly underwhelming this year. He features a .484 OPS against left-handed pitching and he inexplicably has struggled mightily away from PETCO Park, carrying a .208/.308/.306 batting line on the road. He has always played much better at home than on the road throughout his career, but most assumed that was the result of playing his home games in hitter-friendly Arizona. Perhaps there's some bizarre comfort/preparation issue in play. Regardless, Upton's .253/.331/.422 overall line is uninspiring for a bat-first leftfielder and considering that his production has come against right-handed pitching, he doesn't present an upgrade over Chris Coghlan. If the Cubs acquire a bat, I'd be stunned if it was a bat-first corner outfielder.

That leaves Shields and Venable. There's not a ton to say about Shields that we didn't already say last winter. He has been remarkably durable, making at least 31 starts every year from 2007 onward and throwing under 215 innings just once. Shields tends to subside on average strikeouts, low walks, average homers, and by inducing plenty of ground balls. While he's still getting grounders this year, his other numbers have all jumped wildly: his 10.11 K/9 is well in excess of his 7.80 K/9 career rate, his 3.09 BB/9 is a career worst as he's only issued more than 2.35 BB/9 once, and his 1.47 HR/9 is his first total above 1.00 HR/9 since 2010. His strand rate has been a bit better than normal; his BABIP a bit worse. Shields has suffered a slight velocity drop compared to last year, but his pace is right in line with his career norms. He figures to provide roughly one additional win the rest of the way. Unfortunately for Shields, that alarming home run rate doesn't look like a fluke either: his hard-hit rate is the fifth worst among National League starters, placing him in the inglorious company of Kyle Lohse and Jeremy Hellickson.

But man, that contract is rough. $65 million over three years? That's well above what his market dictated last winter and the acquiring team doesn't get the benefit of the youngest year that the Padres bought (this year). For a guy who might reasonably produce 7.5 WAR over the next three years -- assuming his good health remains and his velocity doesn't crater -- Shields is overpaid by something in the territory of 10% or 20%. Not the most appealing target, even if we assume $7 million per win on the open market.

Venable, on the other hand, is the perfect kind of rental for the Cubs, and as a guy who I've had listed as a winter target for months, acquiring him a little early sounds great to me. Let's get something out of the way first: we're not talking about a star or a needle-moving piece. What we are talking about is a guy who hits righties reasonably well (.257/.323/.428 career; a bit better this year), plays an acceptable everyday center field, and who is relatively inexpensive with just $2 million remaining on his deal this year in his age-32 season. I have envisioned sticking Venable in a short-term platoon next year in center with Matt Szczur while the likes of Albert Almora, Jake Hannemann, Donnie Dewees, and perhaps even Ian Happ duke it out for the right to take the job in 2017 or so. When Theo Epstein stated that the Cubs were looking for a left-handed hitting outfielder who could play three or four days a week, it was impossible for me not to think of Venable and smile.

Trade Proposals
I've knocked down Shields in a big way, but it's still worthwhile to imagine what his acquisition might look like as well as picturing some Venable deals.

Proposal #1: Padres trade SP James Shields and $15 million to Cubs for 3B Christian Villanueva and SP Trevor Clifton

This is the kind of territory that the Padres should be expecting for a Shields deal. I'm sure it's tough for them to stomach, but the Cubs provide substantial salary relief in this situation. They agree to take on Shields are basically his market rate in exchange for a couple of assets who aren't the most attractive lottery tickets.

Proposal #2: Padres trade SP James Shields and OF Hunter Renfroe to Cubs for UTIL Arismendy Alcantara, 3B Christian Villanueva, and SP Eric Jokisch

Despite a truly dreadful start to his repeat visit to Double-A, Renfroe has turned it on lately. He's still a boom-or-bust prospect. Still, it may seem bizarre to see San Diego's top prospect included in this deal.

In the event that the Padres want to move all of Shields' salary, I think they're going to have to do something radical like this. Getting Alcantara back is a nice deal for them, particularly given his positional flexibility, and Villanueva and Jokisch can both compete for jobs next year.

Proposal #3: Padres trade CF Will Venable to Cubs for 3B Jeimer Candelario and RP James Norwood

The Cubs send the Padres a legitimately interesting long-term piece in Candelario as well as a bullpen option moving forward in Norwood's big arm. Not the sexiest deal, but one that leaves both teams feeling satisfied.

Proposal #4: Padres trade SP James Shields, CF Will Venable, and $5 million to Cubs for 3B Christian Villanueva, RP Ryan McNeil, and RF Jeffrey Baez

I wanted to come up with a deal that sent both Shields and Venable to the Cubs at the same time. It just doesn't make that much sense still. This is as good as it got for me. I did think that the Padres might prefer to take a flyer on Edwin Jackson's final year next year as opposed to simply including cash in the deal, but then I realized that Jackson doesn't fit San Diego's path at all if they're at all serious about trying to compete next year.

While I suspect that many readers are enticed by the prospect of acquiring Shields for merely taking on much or all of his salary, I urge you to remember that the Cubs' top offer for Shields was for $5 million less over three more valuable years. Shields hasn't done anything this year to up his price tag and there are plenty of reasons to suggest that it should drop instead.

More importantly, fitting Shields into the payroll at $20 million per year all but rules out the possibility of going after younger, better arms like David Price, Jordan Zimmermann, Johnny Cueto, and Jeff Samardzija, arms who will also cost $20 million (or more in the case of Price), but who should be notably more productive. I'd do that third deal for Venable and I'd spend a lot of time thinking about the second one that flips Renfroe and Alcanatara to see if a change of scenery can't reboot both careers.

But make no mistake: I am not at all interested in seeing the Cubs pay an above-market rate for James Shields and giving the Padres a prospect or two for the right to do so. Here's hoping Theo and Jed agree.