- Failing to resign, or offer Kenny Lofton a contract following the 2003 playoff run. This mistake led to Corey Patterson leading off and playing CF, which then led to trading Nolasco, Pinto, and Mitre for a player who is a near certainty to be a one-year temp with the team.
- Passing on, or going weakly for long-term solution free agents Vlad Guerrero, Carlos Beltran, Rafeal Furcal, Kevin Millwood, Miguel Tejada, Billy Wagner, BJ Ryan, Brian Giles, etc. in favor of short-term, over-paid solutions like Jeromy Burnitz, Jacque Jones, Juan Pierre. Outside of Derrek Lee, the team is devoid of young cornerstones who a team can be built around and it's arguable that Lee is even on of those.
- Declining Moises Alou's option and opting to go into 2005 with Jason Dubois and Todd Hollandsworth as the team's sole leftfield options.
- Routinely overspending on bullpen arms: Mike Remlinger, LaTroy Hawkins, Scott Eyre, Bob Howry, Ryan Dempster, etc. With a self-imposed salary cap that will barely be in the highest quartile in the majors in 2007, these types of signings completely disallow making moves for players SUBSTANTIALLY better than league average - Ryan, Wagner, etc.
- Goodwin/Harris/Neifi/Macias/Greive, and on and on - The man has no clue what it takes to build a quality bench.
With a middle infield of Ronny!! and Izturis!!, first base manned by Mabry and Nevin, left-handed pitchers throwing baseballs to Jacque Jones, and a starting rotation that includes Hill, Rusch, Marmol, Marshall, Ryu??? this team WILL MEET THE IMPOSSIBLE!! 100 losses is coming!
Next off season, Jim Hendry will be bought out (Ben Cherrington!!!) and next June the Cubs will be receiving the top pick in each round of the first-year player's draft. Like I said, any trade that condemns Hendry (and hopefully MacFail) and gets the Cubs the top prospect in the 2007 draft is a BOON for Cubs fans.