The Chicago Cubs have had 3 winning seasons in a row and the previous 2 seasons they were the NL Central Division Champion.  There are some teams like the Pittsburgh Pirates, Cincinnati Reds and Kansas City Royals who would love to have that success yet the Cubs are considered a “failure.” It doesn’t help when most in the sports media look down on the Cubs and frequently ridicule them and their fans for what they perceive to be loyalty albeit blind loyalty. 

It is true that the 2009 season was a disappointment and I suppose you could call it a “failure”.  Yet I don’t think the Cubs need a complete overhaul of the roster in 2010 to get back to being a championship-caliber team again.  To me, it starts with the top and Jim Hendry made the worst moves he’s ever made as a GM.  The Cubs let Kerry Wood go because I think they thought Carlos Marmol was ready to succeed him as the closer.  So what do the Cubs do?  They go out and acquire Kevin Gregg from the Marlins then Lou Piniella announces Gregg as the closer during spring training.  Well, that one didn’t work out too well, did it?  Then they dangle Mark DeRosa in a reported trade with the Padres and Phillies in an attempt to get Jake Peavy, but when that deal falls through they then trade DeRosa to the Indians for two minor-league pitchers who don’t contribute anything to the Cubs in 2009.  But the capper is signing well-known attitude problem Milton Bradley as a free agent to give the Cubs “left-handed power.” Now, we all know that Bradley has more baggage than O’Hare International Aiport.  So what prompted Jim Hendry to sign this guy over Bobby Abreu and Raul Ibanez?  Yeah, that one didn’t work out too well either, did it? 

So here we are, Cubs fans, in a place that hasn’t been familiar to us since 2006: no Cubs in the playoffs.  And if 2008 was a disappointment, then 2009 was a catastrophe.  However, new ownership is on the way in the form of Tom Ricketts and many Cubs fans are wondering what he is going to do this offseason.  It is not uncommon to see new ownership replace current management when they arrive.  However, that normally happens with bad teams.  The Cubs have a good team and they’ve had three winning seasons in a row, but no championships.  Also, Jim Hendry and Lou Piniella are still under contract for 2010 so it’s unrealistic to believe that ownership and management will fire them with one season left to go. 

If I was in charge of the Cubs, I would hire a new team executive and the man I’d tab for the job is former Oakland Athletics GM Sandy Alderson.  Alderson recently was with the San Diego Padres and prior to that he worked in the commissioner’s office.  He’s very knowledgeable and has a proven track record as a winner, mostly with Oakland.  He is also regarded as one of Billy Beane’s mentors in Oakland.  We need a new voice in the executive position and Alderson could fit the bill.  After hiring Alderson I would personally fire Jim Hendry as GM and bring in a new GM to replace him.  Of course, I would discuss this with Alderson and I’d let him pick Hendry’s replacement, but one person I’d take a serious look at is Jed Hoyer of the Boston Red Sox.  He’s next in line to Theo Epstein in Boston and when Epstein briefly resigned after the 2005 season, Hoyer was one of a “Gang of Four” including Ben Cherington, Bill Lajoie and Craig Shipley who engineered trades for Josh Beckett, Mike Lowell, Mark Loretta, and Andy Marte.  He also accompanied Theo Epstein to Arizona in November 2003 to persuade Curt Schilling to accept a trade to Boston which he did. 

As for the manager position, I’ve been disappointed with Lou Piniella this year.  At times he has looked tired and lethargic, almost as if he’d rather be anywhere than in the dugout managing the Chicago Cubs.  I could be wrong, but that’s just my perception.  Piniella reportedly will be meeting with Jim Hendry after the season to discuss the coaching staff.  A shakeup could happen, but I would bring back Lou for one more year as I believe most of this season’s disappointment can be pinned on Hendry, not Piniella.  What I would do is bring back Ryne Sandberg as bench coach and move Alan Trammell to third base.  I’d fire Mike Quade, but offer him a position in the organization.  As for hitting coach, I’d probably bring back Von Joshua, but I’d also take a look at former Oakland Athletics hitting coach and former Cub Thad Bosley. 

When it comes to the roster and trades and free-agent signings, I would not bring back Kevin Gregg, Milton Bradley or Alfonso Soriano.  Gregg is a free-agent and I wouldn’t re-sign him for next year.  Bradley and Soriano will be harder to move since they aren’t free agents and have expensive, multi-year contracts.  Soriano has a “no-trade clause” which would make him difficult to move, but it’s not impossible.  Because both players have big contracts I would swap them to other teams in exchange for big contracts they don’t want.  I’d move Milton Bradley to the Giants in exchange for Aaron Rowand.  Rowand could play center field and allow Fukudome to move back to right field where he’s best.  I like Rowand even if he’s not the biggest star because he plays hard and he’s not afraid to run into a wall as he did in Philadelphia.  I’d move Alfonso Soriano to the Dodgers in exchange for Juan Pierre.  Soriano would reunite with Joe Torre and the Dodgers could move him to second base since Manny Ramirez is in left field.  Pierre would return to the Cubs as a left fielder and he’d give them a leadoff man with some speed which they desperately need.  The next move I’d make is signing free agent Roy Halladay.  Halladay would give the Cubs a rotation of Halladay, Zambrano, Dempster, Lilly and possibly Samardzija for 2010.  Not a bad starting five.  Signing Halladay would also send a message to the rest of the league and the fans that Chicago is committed to winning a championship and the new ownership will do anything and everything to make that possible.