What if Jim Hendry Had Been Fired in October 2009?

If the Ricketts had fired Jim Hendry immediately upon taking ownership, what would the Cubs’ drafts have looked like in 2010 and 2011? Would Javier Baez have been a Cub?

Jed-HoyerThe folks over at Blogabull have a post up about the biggest "What-If?" scenarios in the last 10 or so years for the Bulls. These hypothetical flights of fancy are quite a bit more vivid in basketball, where so much hinges the status of a handful of players, but it prompted me to think a little about the Cubs. The one question in recent memory that has always stood out in my mind is: "What if Ricketts had acted quickly and decisively upon taking ownership of the team?" One of the criticisms of Tom Ricketts that followed him from the business world is that he took his time in overhauling operations, waiting until well after it was evident that a change was necessary. I think it's fair to say that the same applies to his tenure of the Cubs, as he waited until midseason of 2011 to change regimes.

There are a lot of ways to go with this question, but I'm going to try to be very narrow in my focus. Let's assume that Ricketts had started the search for a new general manager prior to actually taking ownership of the team. He approaches Theo Epstein, who is quite happy in his Boston paradise, thank you very much, but would strongly recommend Jed Hoyer for the gig. Ricketts takes this idea seriously, and instead of joining the Padres, Jed Hoyer takes over for the Cubs and brings along Jason McLeod to run things on the amateur side. (Hey, this is my hypothetical. Don't like it? Make your own.)

I think it's fair to say that the front office's biggest disappointment since coming on was the implementation of the new CBA almost immediately after their hiring, and it's restriction of compensation picks and draft/international spending. Had they taken over after 2009, what might their big budget drafts in 2010 and 2011 looked like? Fortunately, we have some frame of reference here given that Theo and Jed were heavily involved in drafts for other teams.

2010: No Hayden Simpson!

I'm not sure what the Cubs draft would have looked like in 2010, but saying that Hayden Simpson would not have been a part of it is blatantly obvious. Would the team have opted for big bonus-seeking Zach Lee, whom they coveted in the trade talks for Ryan Dempster last year? Or would it have been eventual Red Sox pick Kolbrin Vitek? Maybe they would have reached for Anthony Ranaudo, knowing he wouldn't have been around in the second.

How about Padres second-rounder Jedd Gyorko at 65 overall? He would look good manning second or third for Cubs right now, and the Padres may not have been on him without Hoyer/McLeod pushing for it. Or would it have been Brandon Workman?

2011: Bullet Dodged?

I'm pretty confident in saying that 2010's draft would have looked a whole lot better (I mean, really: could it have been worse?). 2011? Maybe not. You see, in 2011 the Cubs actually spent money on the draft, shelling out for Javier Baez, Dan Vogelbach, and Dillon Maples, among others. The story goes that Jim Hendry caught wind that the new CBA was coming down the pike and convinced Ricketts to spend big (though I personally suspect that Ricketts himself may have been the driving force). 

In 2011, the Padres picked second baseman Cory Spangenberg 10th overall, immediately after the Cubs took Javier Baez. And, frankly, I don't think Baez would have been a Cub if Hoyer/McLeod were running that draft. Relevant quotes:

McLeod said there were two players selected before Spangenberg the organization liked, though they essentially got the guy they wanted.

I'm going to assume those two players were Rice third baseman Anthony Rendon, and one of the pitchers (likely Gerrit Cole), given this statement from Hoyer:

“He’s the second-best hitter in the country,” said Hoyer. “For a while, I thought he was our sleeper, but he hit his way out of that.”

And then there's this anecdote from McLeod:

McLeod had just scouted Baez, who played for Arlington Country Day, a Jacksonville private school that became a kind of barnstorming team after withdrawing from the Florida High School Athletic Association.

The competition was suspect and McLeod had no idea what he’d just seen, telling Hoyer: “I don’t know if this kid is going to be Manny Ramirez or not get to Double-A.”

Now, Baez is no sure thing (though, wow), but no GM on Earth is trading him straight-up for Cory Spangenberg at the moment.

Maybe you want to take the hypothetical further, and suppose that the Cubs would have started shedding older talent in 2010 and ended up with a higher pick. Would we be talking about the young infield tandem of Gyorko and Rendon right now? Would this front office even given a thought to Dan Vogelbach?

 

What are your all-time Cub "What-If's?"

Cubs weighing Dodgers trade offer for Ryan Dempster

The Cubs are weighing an offer they have received from the Dodgers for Ryan Dempster

ST. LOUIS — Ryan Dempster is still scheduled to start against the Cardinals on Friday night for the Cubs, who are considering the latest offer from the Dodgers for the right-hander.

According to MLB.com's Ken Gurnick, the Dodgers have made an offer, but they won't get into a bidding war because they also need to add offense, preferably a corner infielder, even more than they need Dempster. The Dodgers' farm system also is a little thin in the kind of prospects needed to land All-Star caliber players like Dempster, the Padres' Chase Headley or the Phillies' Shane Victorino. Cubs president of baseball operations Theo Epstein has said he's looking to improve on pitching in the organization.

That said, Dempster, 35, would be a pure rental for the Dodgers, which most likely is affecting the negotiations. Dempster is in the last year of his four-year contract, which is paying him $14 million this season. Players must be with a team for an entire season in order to qualify for Draft-pick compensation, according to the new CBA.

Not too surprisingly, Zach Lee will not be involved in the trade. The draft pick compensation is no doubt going to earn the Cubs less for Dempster than they'd have received a year ago. 

Zach Lee won’t be traded for a rental like Ryan Dempster

The Dodgers top prospect, and the midseason #49 prospect (Baseball America) Zach Lee won't be traded for a rental according to Ken Rosenthal.

Dodgers propose trade for Ryan Dempster

Bruce Levine is reporting that the Cubs have received a trade proposal for Ryan Dempster though the specifics are unknown. 

CHICAGO — The Los Angeles Dodgers have proposed a trade for Chicago Cubs starter Ryan Dempster, a baseball source told

The Cubs have been clear their top priority on the trade market is adding young pitching. It is unclear whether Zach Lee, the top-rated arm in Los Angeles' farm system, is included in the offer.

The Cubs appear to be making contingency plans in case a Dempster trade is completed. A major league source told ESPNChicago.com that talks are fluid and the team is preparing to have replacements in St. Louis this weekend in case a deal is completed for the veteran starter.

In what could be the first move of an active stretch, the Cubs acquired pitcher Justin Germano from the Boston Red Sox for cash considerations Thursday. In a corresponding transaction, right-hander Jairo Asencio was designated for assignment.

If the Cubs can get Lee for Dempster I'm going to be ecstatic. Lee was a midseason 49th ranked prospect by Baseball America. His value as a prospect would easily be $15 million so that would be a fantastic deal for the Cubs. It's hard for me to imagine the Dodgers giving up that much for a rental, but stranger things have probably happened.

Lee is a big guy and here's what Baseball America had to say prior to the season:

Lee has a deep arsenal and the pitchability to get the most out of it. His fastball generally ranges from 89-93 mph, but he can reach back for more when he needs it, touching as high as 98. He's a strike-thrower who commands his fastball to both sides of the plate. He also has an advanced feel for manipulating the ball to make it do what he wants against certain hitters. He can make his fastball sink, or turn it into a cutter that developed into a true weapon. Lee featured a hard curveball that tended to get slurvy in high school, but he worked on developing both a curve and slider as separate offerings in 2011. He made huge strides with the slider by the end of the season, allowing him to get in on the hands of lefthanders, who he held to a .229/.291/.341 line. The curve still shows promising spin and depth at 79-83 mph when it's on, but it continues to come and go. He also features an 81-84 mph changeup that has a chance to be an average pitch down the road.

I'll be surprised if the Cubs do this well. He's the top ranked Dodgers prospect and I just don't see an organization giving him up for Dempster's 2 months. Especially when you consider the Dodgers can't get draft picks at the end of the contract.

Justin Germano is 29 years old and has an ERA near 5 in 258 innings at the big league level. The guy has had fantastic control in the minor leagues (walks per 9 of about 1 to 2 over the last several years). His K/BB this year is over 5. I think he could fill in better than Chris Volstad could so this is a solid pick up for the Cubs.