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The Wheelhouse: So You Want to Be a GM?

Derek VanRiper

Derek VanRiper

Derek is the Senior Baseball Editor for RotoWire.com, where he's been a two-time finalist for the FSWA's Baseball Writer of the Year award, and winner of the Best Football Article on the Web (2009) and Best Baseball Article on the Web (2010) awards. Derek also co-hosts RotoWire Fantasy Sports Today on SiriusXM Fantasy Sports Radio (XM 87, Sirius 210) from 11a-2p ET on Tuesdays and Wednesdays.

Like most people who play fantasy baseball, I believe that I could successfully work in a major league front office. Ultimately, most of us want to be a general manager, and that's what keeps us coming back year after to year in our attempts at rotisserie domination.

Bad trades in the big leagues only amplify the voice in my head telling me that I could at least prevent mistakes, if not become an executive capable of consistently improving a big franchise.

Even with the understanding that the job is much more complex and difficult than most of us will ever know, I cannot figure out what compelled Royals general manager Dayton Moore to flip one of his starting pitching prospects at High-A (Kyle Smith) to the Astros for Justin Maxwell.

This comes from a guy who liked Maxwell back in his days with the Nationals and wanted to see what he could do with consistent big league at-bats. Injuries kept that from happening, and he bounced around a few organizations before finding a temporary home with playing time in Houston last season.

If this were 2008, it would have been an easy trade to rationalize. It would have been a good trade at that time. A toolsy 24-year-old outfielder with a mix of power and speed that enabled him to play all three outfield spots? Sign me up. Unfortunately for the Royals, it's 2013. Maxwell will turn 30 in November and the trade looks more like a terminable offense. Maxwell was designated for assignment by the Yankees 16 months ago and the Astros claimed him off of waivers. That marked the second time in his career that Maxwell was DFA'd, with the first coming from the Nationals 15 months earlier.

Smith is hardly an elite prospect, but the Royals' lack of viable arms at the big league level prompted Moore to make the Wil Myers-James Shields trade with the Rays this winter. It looked bad at the time, and it looks worse now. Shields is under contract through the end of next season, which could change during the winter, but consider the following.

Ervin Santana is in his walk year. In fairness, Moore should receive credit for making a nice addition to an area of need. Long term, however, what type of commitment can you make to him given the concerns about the health of his elbow?

Jeremy Guthrie is signed through 2015. To this point, he's been a tick below replacement level (-0.1 WAR). If he's able to replicate the final two years of his time in Baltimore, maybe he's a two-win starter at most in 2014 and 2015. Most likely, he's something in between that level and what he's done during his time in Colorado and Kansas City - an innings-eater suitable to be a No. 5 starter.

Wade Davis has been better in a real-life sense than you might think (5.50 ERA, 4.14 xFIP, 1.2 WAR) and is controllable through 2017 thanks to a guaranteed $4.8 million in 2014 and three club options at $7, $8 and $10 million. He'll turn 28 in September, and may not have much growth left at this stage, but it's not out of the question to think he might be a No. 4 starter for the duration of the contract.

If that is your current rotation construction, how can you give up a promising arm for a 30-year-old platoon outfielder?

The Royals are three games over .500 and 6.5 games behind the Tigers in the American League Central entering play Friday. Currently, they're 4.5 back of the Indians for the second Wild Card.

Maybe this small deal was in line with what the Pirates did at the deadline in 2011 and 2012, pushing for a couple of pieces that would attempt to show the fanbase that they believe they are close to contending, without fully mortgaging the future by going all in and dealing away Kyle Zimmer, Adalberto Mondesi and/or Bubba Starling.

The problem, however, lies in the fact that the Royals' farm system, which thanks to promotions and weaker draft classes in recent years did not rank in the top half of the league entering the season according to Baseball America. The low-cost, moderate upgrade method made sense for the Pirates, who have a better wave of young talent position to infuse the big league roster in the coming years.

A 29-year-old outfielder that can mash left-handed pitching (career: .255/.373/.455), but can't hit righties (.203/.271/.396) is a complementary piece at best. If history is any indication, Maxwell is just as likely to be designated for assignment again by this time next year as he is to have value to the Royals as part of an outfield platoon.

If this trade were just the footnote for a busy deadline day where the Royals acquired another starting pitcher and a quality right fielder, it would be an overpay but one Kansas City fans could live with simply because of the associated moves.

Instead, it looks like another instance where the Royals became the butt of a joke, failing to make a move that would significantly help them make a run at a playoff spot, while showing a costly sliver of discontent that ultimately weakens the team in the long run.

Long story short, it's very difficult to justify giving up anything of potential long-term value for someone who has been designated for assignment twice in the last 20 months.

This year's non-waiver deadline was a bust, although the two biggest names on the move - Jake Peavy and Matt Garza - were a part of trades prior to July 31, so taking a 10-day view of the deadline makes things a bit more bountiful.

In my ongoing effort to try and get a feel for what being an actual general manager might be like, I took on a team on behalf of RotoWire in a league called The Big Show - a 24-team simulation league that utilizes linear weights to replicate a full 162-game regular season. In The Big Show, we have 80-man organizational rosters, so the first-year player draft each spring covers the players selected by MLB teams the previous June as well as any other unrostered minor league players without big league service time. Young talent, just as it as in MLB, for the same cost-control reasons, is a huge part of building a viable long-term organization. One slight difference between MLB and The Big Show is that Big Show franchises are limited to a $120 million salary cap.

Still, the degree to which the league mimics managing a real roster goes as deep as any league I've been a part of.

Since taking over prior to last season, there has been incremental progress in the wins department, but the core of the roster inherited wasn't quite good enough to take that next step. After selling off expiring pieces at the trade deadline last summer, a full-scale rebuild became the course of action this time around.

If you have ever played in a Score Sheet league, you have a good grasp on the importance of starting pitching depth. While our farm system was at least average compared to the others in our league upon take over, it was stocked mostly with position players (outfielders) and was extremely thin on pitching.

Major league general managers are indirectly accountable to their fan base by being accountable to ownership and the team's marketing department. Of course, in a simulation league, the negative consequences of trading away star player and deconstructing a roster are significantly less than they would be when you need to hit revenue targets and keep fans interested.

Thus, to be accountable and hopefully learn from my mistakes from the last 17 months, here's a look at the trades that I have made over the past two seasons.

5/12: Acquired RHP Tanner Scheppers for LHP Barry Zito.

Although Zito was signed for a mere $1.33 million in 2013 with a $1.29 million option for 2014, the opportunity to get six years of control on what I believed to be a one-day dominant reliever was well worth it. Surprisingly, Scheppers has a 0.3-0.0 edge in WAR this season over Zito, but this was about getting rid of a potential Old Maid card before he had no value to other teams even in a league where warm bodies to eat innings are useful.

7/12: Acquired 3B Alberto Callaspo and RHP Neil Ramirez for 3B Ryan Zimmerman.

Draft pick compensation was the better play in hindsight, although Callaspo filled an organizational need at third base (still having two arbitration years remaining, and sneaky value as a 2.5-3.0 win player the previous two seasons) with Zimmerman's upcoming departure and Ramirez was a buy-low attempt on an arm that has possesses good stuff, without consistency and control in the upper levels of the minors. Zimmerman would have landed a compensation round pick in the 25-28 overall range, where Paco Rodriguez, Chris Stratton, Joey Gallo and Lucas Sims were selected.

7/12: Acquired a 2013 fifth-round draft pick and 1B/OF Aaron Westlake for Carlos Lee.

Westlake washed out as an offseason cut, but the fifth-round pick was used to selected Red Sox right-hander Ty Buttrey. It's far too early to draw a meaningful conclusion on Buttrey (he's currently a short-season Lowell), but getting a young arm for two months of an expiring Lee seemed adequate.

7/12: Acquired LHP John Gast, LHP Braulio Lara and RHP Ryan Webb for C A.J. Ellis and INF Willie Bloomquist.

With Wilin Rosario and Chris Iannetta on the roster, moving Ellis in what looked like a possible peak in his value was the aim here. Put simply, it was a bad evaluation of his skills on my part, especially when you consider that he had accrued no service time prior to the start of our 2012 season. If nothing else, he could have been stashed away at Triple-A until a backup to Rosario was needed following a later trade of Iannetta.

Before undergoing season-ending shoulder surgery, Gast was making this trade look like salvageable. Unfortunately, his uncertain health and Ellis' steady production at a premium spot make this one a complete loss on my end barring something unforeseen. Lara is struggling with walks as a reliever at Double-A, but the new role increases his chances of making it to the big leagues. Webb is a replacement level reliever, but perhaps he will net an extra draft pick via trade in the near future.

7/12: Acquired RHP Alex Cobb, RHP Wilmer Font and RHP Brad Brach for CC Sabathia and a 2013 fifth-round pick.

Sabathia was an expiring contract and at the deadline last year, moving him while covering his remaining salary for the season landed us a very good mid-rotation starter in Cobb for the next six years. Brach has been a replacement level reliever so far this season after finishing at -0.7 WAR a year ago, but his issue in San Diego has been walks, which could eventually dissipate if his track record of control in the minors is any indication. Font was at the time, and still is, a lottery ticket with a live arm.

Kudos to the Brooklyn 42's (the organization on the other side of this deal), who turned that fifth-round pick into Danny Salazar, who simply was not my radar when I selected Buttrey five picks earlier.

12/12: Traded 3B Alberto Callaspo for RHP Liam Hendriks

If you did not believe me when I said that pitching depth is important and that the roster was truly lacking it, this trade should be proof. Callaspo has had a significantly down year, and dealing him free up some money ($4.5 million). Hendriks has shown good control (47:12 K:BB in 79 innings), but has been very hittable at Triple-A Rochester and is hardly a lock to start effectively as a big leaguer down the road on his current path. On the bright side, he's only 24, so perhaps there's still some development left.

12/12: Acquired RHP Shaun Marcum and INF Jordan Pacheco for C Chris Iannetta, 1B Brett Wallace and RHP Marcus Mateo.

The interest in trading Iannetta was two-fold. First, Wilin Rosario is a cheap long-term solution in my catcher spot. Second (and more importantly), the previous franchise owner/general manager had signed Iannetta to a long-term deal through 2015 and he was still owed $31.75 million. Marcum, conversely, was owed $19.725 million through 2014 and at least filled a dire organizational need despite a very lengthy injury history.

12/12: Acquired RHP Cody Allen and RHP Jeremy Hefner along with a 2013 fifth-round pick for RHP Joel Hanrahan and OF Seth Smith.

Yet another spot where money was trimmed in the form of arbitration-eligible players (Smith - $3.6M, Hanrahan - $4.1M). I had some concern that Smith's playing time was going to dry up in a crowded Oakland outfield, and Hanrahan's control issues in 2012 made me question whether he was going to rebound skills wise and earn anything more than that salary. The point became moot when he got hurt, but shaving $6.3M from the payroll (when accounting for Allen and Hefner coming back) was helpful. Six years each of Allen and Hefner were also enticing, while Hefner looked like he had a clear path to chewing up innings as the fifth starter given that he needed Johan Santana or Shaun Marcum to get hurt in order to have a clear spot.

2/13: Acquired OF/1B Michael Cuddyer and an eighth-round pick for INF D.J. LeMahieu, OF Tyler Moore and the fifth-round pick acquired from the Carlos Lee deal in July of 2012.

Cuddyer has been outstanding this year, and as an expiring contract with a 2013 salary at $9.5 million (no 2014 option), he was a good short-term replacement in right field for Smith. The eighth-round pick became Indians prospect Kieran Lovegrove. Like Buttrey, it's far too soon to gauge what he's going to be worth in the long run.

5/13: Acquired INF Nick Punto for a 2014 sixth-round draft pick and $200,000 cash.

Depth, and nothing else. Remember, defense and versatility are actually somewhat useful in a simulation format. Neil Walker was on the disabled list earlier this season and a lack of second-base eligible players prompted the minor deal for Punto. The $200K essentially covers the signing bonus of the player that will be selected with that sixth-round pick, which I might simply get back from another team in a future trade anyway.

5/13: Acquired OF Reymond Fuentes for RHP Shaun Marcum and $3 million in cash.

Of the $19.725 million on Marcum's deal in 2013 and 2014, $12 million was coming in 2014. Seeing an opportunity to offset the risk, cutting the rest of his salary for the current season and saving another $9 million in 2014 made sense. Fuentes, one of the key pieces in the Red Sox-Padres trade involving Adrian Gonzalez a few seasons ago, has recouped his prospect status at Double-A in his age-22 campaign with a .308/.381/.428 line including a 28-for-37 mark as a basestealer in San Antonio.

7/13: Acquired RHP Robert Stephenson, RHP Jose Dominguez, OF Chris Heisey and 3B Matt Dean for CF Dexter Fowler and OF/1B Michael Cuddyer.

As mentioned before, Cuddyer's contract was set to run out at the end of 2013. Considering the cost of acquisition, this was a pretty strong return since Fowler has only two (likely costly) arbitration years left before free agency in our league. He's on track for a career-best 3.5 WAR season, but his three-year plate discipline and ISO marks lead me to believe that this might actually be his career year, or at least, a plateau in his development. The downside, is a possible trade out of Colorado in the offseason given their glut of options at the position and his career numbers outside of Coors Field (.245/.335/.369). With four homers in his last 62 games, the power surge April looks like an aberration as well. He's valuable, but in this setting, it was difficult to see his value getting any higher.

Stephenson continues to ascend toward Cincinnati with the look for a future frontline starter. Possessing a fastball that can touch 100 mph with movement, he also has a pair of good second offerings including a curveball and changeup. The Reds recently promoted Stephenson to High-A Bakersfield where he's turned in two strong starters and a clunker while carrying a 13:1 K:BB in 14.2 innings after a 96:20 mark in 77 frames with Low-A Dayton to begin the year.

Dominguez was suspended in 2010 as a minor leaguers for testing positive for Stanozolol - and subsequently received another 25-game suspension in November for a banned substance or refusing to cooperate with the league's drug treatment program. In any case, he seems to have plenty of risk of future disciplinary action, but lights up the radar gun with a triple digit fastball. After piling up a 40:13 K:BB between Chattanooga and Albuquerque in 25.1 innings, Dominguez was promoted to Los Angeles and has since landed on the 15-day DL with a strained hamstring.

Once a supporter of the "Free Chris Heisey" movement, I have resigned to the idea that he's just a fourth outfielder and little more. Without Fowler and Cuddyer, he'll cheaply take up space for the rest of 2013 before moving into a less significant role on my club next season.

Dean, just 20 years old, is a long-term investment, but he's playing well in the Appalachian League with Bluefield in the Blue Jays' system through 37 games with a .296/.360/.443 line. His plate discipline is a work in progress (12:37 BB:K, 122 at-bats), but could be worse. Considered to be very raw, Dean has a chance to be a good defender at a valuable position with power to all fields if he's able to clean up his swing mechanics over the course of his development.

7/13: Acquired RHP Jordan Swagerty for OF Jonny Gomes.

We know what Gomes is at this stage and sim leagues don't value clubhouse presence. Swagerty is a former second-round pick in the Cardinals' system making his way back from Tommy John surgery. Between the Gulf Coast League and Florida State League, Swagerty has pitched in nine games this season (10.2 innings) working mostly as a reliever. It's unclear if that is a rehab-based decision, or a permanent shift from the St. Louis decision makers. Prior to going under the knife, he touched 96 mph with his fastball and had a very good curveball, projecting as a future closer or possible mid-rotation starter depending on the potential development of a third pitch.

7/13: Acquired RHP Jameson Taillon, OF Mason Williams, RHP Matt Barnes, RHP Jose Campos and OF Junior Lake for 1B Joey Votto.

This trade could/would never happen in real life. At least, not in July, but I felt like the offer for Votto (signed at $15M, $16.25M and $17.75M through 2016) was one that could not be passed up. Finding another organization willing to give up fewer players, but one elite position prospect never really went anywhere. Previous attempts to field offers often fell well short, but this time around, it just made sense to make the franchise much more talent rich in the long haul. Winning without Votto is going to be difficult, but consider the quality within the 30 years of club control in the return, and that with the $49 million available to spend over the next three seasons without him, there will be additional replacement value in free agency or through other acquisitions in trade.

Taillon is the most highly regarded piece coming back, and was labeled a 65 in the Baseball America Prospect Handbook this spring. His combination of velocity, movement, command and secondary offerings at age-21 make him an elite talent. With a 106:36 K:BB over 110.1 innings at Altoona, he is closing in on joining the rotation in Pittsburgh. The Bucs chose not to acquire another starting pitcher at the non-waiver trade deadline and Taillon could enter the equation should the need arise due to an injury in front of him. It may ultimately hinge on how well he pitches at Triple-A Indianapolis after being promoted Friday.

Williams also received a 65 grade in his 2013 BA ranking, although his tools are still being refined at High-A. Just 21 years old, the former fourth-round pick could see the big leagues at some point in 2014, but perhaps not as early as previously expected as he's hitting .274/.341/.372 over 89 games in the Florida State League. Although he is still somewhat raw, Williams has shown an improving eye including a career-high 8.8 percent walk rate, while maintaining a low strikeout rate (12.7%). Power is projected in his development, so perhaps Williams will become a better long-term option in center field than Dexter Fowler (who had just two years remaining before free agency) for my franchise.

Barnes has been missing bats at an excellent clip, ranking third in the Eastern League with 113 strikeouts despite having logged just 88.1 innings. Taken 19th overall by the Red Sox in 2011, Barnes set whiff records at the University of Connecticut, while his greatest hurdle in getting to the big leagues will be cutting back on the free passes. Graded as a 60 entering the season, Barnes has a handful of intriguing similarities to Matt Harvey both in his write-up, but also in his development to this point. Expecting Barnes to become another Harvey is foolish, but it's a good reminder that the light bulb can turn on in terms of command even with a move into the big leagues.

Campos turned 21 in July, but he's far behind the other prospects acquired in this deal in terms of his progress. Currently working at Low-A Charleston, he's posted good numbers with a 70:16 K:BB, 1.29 GO/AO and just four homers allowed in 77 innings. Campos suffered a fractured elbow in 2012 and also spent time on the disabled list in May. Prior to the injury this season, Campos had shown diminished velocity and drew a less than encouraging scouting report from ESPN's Keith Law via River Avenue Blues.

I saw Junior Lake play in the Arizona Fall League in 2011, when he was still being played as a middle infielder. Even if Starlin Castro didn't exist, Lake wasn't going to stick at shortstop because of his size, but his raw tools have always kept him on the prospect radar. Now playing left field for the Cubs, Lake has the arm strength to move to right once Nate Schierholtz is out of the picture, however, and his early production at the plate is on par with the tools he has inconsistently displayed in his development. Plate discipline is a short-term concern, as he walked just 5.9% of the time at Iowa this season and is drawing free passes at a 3.1% clip so far in Chicago. At the very least, he should have a couple of years to play regularly if he can hold his own before the Cubs are positioned to upgrade if he turns out to be merely an average option in a corner-outfield spot.

7/13: Acquired LHP Enny Romero and a PTBNL (Andrew Heaney) for DH David Ortiz.

Ortiz should outperform his $11 million option for 2014, but maximizing long-term value for one year and changes of his services was necessary.

Still working as a starter at Double-A, Romero fits the ball as a very projectable left-hander, but his long-term home will eventually be the bullpen if he's able to iron out his command issues. With a fastball that can reach 97 mph, a curveball and a changeup that is still a work in progress, the tools are certainly there, it's just matter of the Rays' ability to help him harness it.

Heaney is the better piece here, technically a PTBNL because he was drafted in our league back in March. Promoted to Double-A Jacksonville after a dominant stretch at High-A Jupiter. Also projected as a 60 by Baseball America, Heaney could quickly become the Marlins' No. 2 option in the rotation behind young ace Jose Fernandez.

7/13: Acquired DH Raul Ibanez for a 2013 fifth-round pick.

After trading Ortiz, Votto, Cuddyer and Fowler, the major league roster was light on guys to simply take up space for the rest of the season. The anticipation here is that further moves will be made to recoup this pick anyway from another club, so having Ibanez play out his expiring contract on my roster is essentially a move to have a complete 25-man roster.

From all of the moves I've made so far, I have nearly $75 million to spend in player acquisitions toward the 2014 salary cap. Perhaps half of that will end up going to free agents, while the rest will likely be part of trades similar to the Cuddyer deal I made this past spring where another club is looking to unload salary to increase their short-term flexibility. Going that route, I can safely avoid overcommitting to costly free agents, while quickly supplementing the young talent on the roster with veterans capable of quickly making this team competitive in the short term.

The playoff window may not fully open until after 2014, but it's proven easy enough to move expiring assets in each of the past two seasons where making a strong effort to win next season could payoff in the form of long-term value, if not in the form of push into the postseason.

As for my criticism of Moore, an extremely scaled-down version of running a franchise has already provided a couple of costly lessons and the Zimmerman trade in particular looks awful since Callaspo wouldn't have been a 2.5-3.0 win player this year at an area of need, and my subsequent Callaspo trade only netted Liam Hendriks. For rotisserie players in dynasty leagues, and even those in redraft leagues where a high number of transactions have been made throughout the season, reviewing the past year (or year-plus, in multi-year formats) can be very beneficial.

For those interested looking at the roster as it is now constructed, I've imported the team information here for RotoWire's franchise in The Big Show for public viewing.

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