What has this team done since the Ricketts took over ownership? Payroll dropped, wins went further down...
The "out of context" bottom line is that the Major League team has regressed with Ricketts as the owner.
In context the Ricketts ownership started off relatively slow as they seemingly mismanaged a few early moves and made some questionable decisions regarding the end of the Hendry Regime. The Cubs were slow to ditch Hendry IMO and made some hires (Oneri being the most well known) without having a GM to consult. Then there were a few PR debacles, the most infamous being Papa Ricketts involvement with a group that is aimed at discrediting the Obama administration, which regardless of your political motivations is a misstep in Rahm's Chicago. That news broke right as the Cubs were going to ask for public funding and well the whole thing went to shit.
The Hendry slow reaction worked to the Cubs benefit, however, as Theo Epstein was dumped in Boston and suddenly became very available. Ricketts made the hire and gave Theo free run over rebuilding the organization from the ground up.
Now here there are a lot of small details that you likely don't care about, but are important according to very smart baseball people both in the media, in the industry, in the industry after being in the media, and in the media while being fresh out of the industry. The Cubs have begun to build up an infrastructure that will support both player scouting and development while also spending money to renovate Wrigley and creating a floor plan to completely overhaul the stadium to better suit its fans and create extra streams of revenue.
On the scouting and development side the Cubs have increased their scouting department, modernized the front office, invested money in foreign markets like Venezuela, the DR, and Asia (a controversial market). Through 1 draft cycle this front office has acquired 5 of the Cubs top ten prospects and I believe 3 of them made the BP Top 101 list (Albert Almora, Jorge Soler, Arodys Vizcaino). The gains the Cubs have made in the DR and Ven. won't bee seen for a few years but having academies in both areas is certainly a boost.
From the MLB standpoint any gains the Cubs have made are minimal, but there is some general optimism about the roster this year. They won't make the playoffs but 75-80 wins is not ridiculous. Given the injury to Matt Garza the Cubs made a lot of smart moves given the FA market and their main weakness last year, which was Starting Pitching.
So yes, out of context the Cubs have regressed at the MLB level every year. It's a different story in context, in my opinion.