It might not be quite the winter of his discontent, but this off-season hasn't been a whole lot of fun for Theo Epstein.
While the Cubs wait and wait and wait for something to happen that will increase revenue and allow them to start competing for expensive talent, they must endure the taunts of fans, media, players and even agents.
It was at the winter meetings that Scott Boras mocked the Cubs for their small-market operation.
The Jeff Samardzija talks started long before that and continue to go nowhere fast -- with Samardzija acting like a perennial Cy Young Award winner.
There are radio and TV deals to be negotiated, but the best of that television money is five long years away.
They have to beg the city to let them spend their own money and rebuild their crumbling ballpark, desperate to bring in new streams of cash -- or even sport a clubhouse worthy of a major-league team -- but that humiliation goes on and on.
Washington pols look efficient compared to the Cubs' business operation, which continues to be tortured and embarrassed by the rooftop owners, who prevent the Cubs from putting a single trowel in the ground.
But the cherry on top of the hot-manure sundae was the Masahiro Tanaka result.
The story should have been that the Cubs threw a pile of money on the table, took the gamble and made an attempt to secure a coveted Japanese free agent.
It was surprising because the Cubs are said to be short on cash and unable to compete -- even if they had a reason to compete for big-money players. The notion that they aren't in a position to spend that money -- with their young players still a ways away -- made the Tanaka bid surprising and exciting for Cubs fans.
That's where the story should have ended. Good for the Cubs for taking a shot. Can't blame them when another club went crazy in the process, pouring $35 million more than the Cubs into that deal. It was fun while it lasted. Praise all around.
Instead, the Cubs took a beating -- again.
Why? Because Cubs fans were sold on the idea that the Cubs would not be outbid for Tanaka.
This silly story was leaked by someone in the Cubs' organization -- likely from the business side -- continuing a pattern of misinformation and inaccurate headlines that only serve to make baseball operations look bad.
Even if there's no malice aforethought, and it's likely there's not, the end result is the same.
The Cubs look bad for not getting Tanaka after someone got the hopes up of fans desperate for a reason to be interested in 2014.
The Cubs look bad for falling woefully short when they were supposedly the high bidder.
The Cubs look bad because they can't get anything done.
And this is because someone with the Cubs keeps passing out bad information for purposes that escape, one would imagine, the grasp of those in baseball operations.
Epstein much prefers to undersell and over-perform, while someone on the flip side continues to force stories into the media, not the least of which was how Joe Girardi would be the next manager.
It was another fantasy that did nothing to help baseball ops, especially after they hired Rick Renteria, an uninspiring choice among fans in the wake of Girardi staying in New York.
At the convention, there was all manner of misstep, further antagonizing the rooftops and mocking those with whom the Cubs fight.
And when pressed on the issue of the Cubs' relationship with Phillies manager Ryne Sandberg, the marketing boss made it sound terrific and said Sandberg was invited to the convention.
According to Sandberg, this is patently untrue.
The unfortunate result of a disastrous winter is it leaves fans wondering if anyone with the Cubs is being honest about anything, when the baseball side has taken great pains to be open about their plans.
"We've been really transparent about what we're trying to get done here," said GM Jed Hoyer. "We really like our foundation, but we know we have to translate that foundation into wins and losses."
That is still the future and this is the present that Epstein has to deal with, someone chopping his legs out from under him from within his own organization, consistently undermining his attempt to manage the message.
You can't help but wonder how long Epstein can put up with it.
•Hear Barry Rozner on WSCR 670-AM and follow him @BarryRozner on Twitter.