The Ricketts family is the least desirable bidder for Chelsea

Earlier this week, Gabe Henderson wrote up an excellent summary of the Ricketts family’s problematic history. The article went on to clarify why the past comments of patriarch, Joe Ricketts, should disqualify the family’s bid to purchase Chelsea out of hand, even if the bid itself is technically only tied to three of his children. There’s no question the Ricketts would walk into the club with a cloud of controversy over them from day one, and PR would be an uphill battle from the get-go. Put simply, The Raine Group has bids with less baggage (and more money) to consider.

All of that being said, you can set all the political and ethical quandaries aside and still have a perfectly reasonable argument as to why the Ricketts are among the least desirable bidders to have a serious chance of being selected.

The Ricketts’ main claim to fame is their ownership of the Chicago Cubs, the historic Major League Baseball franchise who won its first World Series title in over 100 years in 2016, ending one of longest trophy droughts in sports history (so stop complaining, Tottenham fans). Having purchased the team in 2009, the Ricketts oversaw a competitive and infrastructural renaissance that brought one of the preeminent “lovable loser” franchises to the promised land.

The reality, however, is that the one World Series trophy has been little more than a fancy coat of paint on a rickety (pun intended), beat up hatchback hardly fit for purpose. The Cubs are not a case study on how to successfully run a team, and a Ricketts takeover at Chelsea could be a veritable death knell for the club as a consistent top-level contender.

The Ricketts family is the least desirable bidder for Chelsea for multiple reasons

Despite the cultural love for Moneyball, Leicester City and all the other bright-eyed, “David vs. Goliath” dreams of the sports idealist, winning silverware in professional sports is largely a matter of outspending your competition. All while still having some semblance of a plan to build a functioning team. Regardless of how a sport and its league(s) are structured, spending (particularly on salaries) is closely correlated to winning, regardless of salary caps, Financial Fair Play or any other nominal restriction meant to maintain a modicum of competitive parity despite inherent financial inequalities. Is it romantic? God no. But it’s the philosophy that got the Blues to the top of the mountain, just like plenty of teams prior and since.

Baseball is no different. It is perhaps the closest American equivalent to the type of laissez-faire capitalism that rules European football, although crucially it still has the ironically American tradition of a safety net for bad teams. Unlike most American sports though, the MLB has no salary cap, the (usually soft) limit on how much money a team can collectively pay its players. The NBA, by comparison, will have a salary cap of $121 million for the 2022/23 season, meaning the combined annual salary of a team’s 15-player roster must add up to no more than the aforementioned figure. Teams can exceed this number, but any amount over that is subject to a massive “luxury tax.” This is the league’s way of letting teams indulge to a limited extent while still exerting some downward pressure to maintain something approaching competitive equality. Baseball, like football, scoffs at the idea of competitive balance and looking out for the little guys.

You want to get good? Get rich.

At least at the surface level, you can’t accuse the Ricketts of being unaware of the importance of spending. The Cubs have long had one of the highest payrolls in the MLB season after season (a product of being in a big market) and tended to be a middle of the road team that never seriously contended for the World Series.

In the two years prior the Ricketts’ purchase of the club, the Cubs had the third highest payroll each season. They also had the 12th and second best records (out of 30) in the league in those years, 2007 and 2008, respectively. They made the playoffs in both seasons. In 2009, the Ricketts took control and immediately began to pump more money into the team. Meanwhile, the on-field performance cratered. 2009, 2010 and 2011 saw the Cubs as the second, first and second highest paying team while achieving the 16th, 23rd and 26th best records. 2012, 2013 and 2014 were even worse (29th, 26th and 22nd by record), and the Ricketts’ investment fell off (seventh, seventh and 13th by payroll). Needless to say, the Cubs didn’t make the playoffs any of those seasons, rendering the first six seasons of the Ricketts’ ownership a complete wash.

It’s worth noting that 2012 was the start of a purposeful rebuilding process for the Cubs. The highly coveted Theo Epstein was hired as team president and began a process of developing young talent at the expense of winning (or even trying to win, for that matter). They were tanking, plain and simple. It’s an unsavory—yet all-too-common—practice in American sports, but it’s obviously not a realistic strategy in European football. Losing gets you relegated into obscurity, not the first pick in the next draft.

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That process, however, did pay dividends in 2015, 2016 and 2017. Some of the young talent that Chicago had invested in began to bear fruit. A sudden uptick in spending accompanied an equally sudden uptick in results with the team winning the World Series in 2016 and reaching the semifinals on either side of that. It can’t be emphasized enough how monumental an achievement this was, and how meaningful it was to lifelong Cubs fans. It’s understandable that some people out there will say that one World Series trophy absolves the Ricketts of every unlikeable move they made along the way. From the perspective of a Chelsea fan, however, a slow build to a single achievement would feel like a major step backwards for a club that expects to compete for multiple trophies every season.

Those halcyon days were short-lived though. 2018, 2019 and 2020 saw a further rise in spending, but results began to falter. Over those three seasons, the Cubs were third, first and second in spending, but only managed the sixth, 14th and ninth best records, respectively. The glory days of the mid-2010s were laid to rest just as quickly as they’d arrived.

That brings us to the 2021 season and perhaps the most concerning set of behavior from a Blues fans’ perspective. With Epstein leaving the organization and a hefty payroll to account for, the Ricketts decided to lean into the downturn and tore the team down to the studs. The result was the 24th best record in the league and a roster shorn of its best and most beloved players, ostensibly in an effort to save some money and kickstart another cycle of tanking and rebuilding.

It’s hard to come up with an equivalency to how brutal the Ricketts’ disembowelment of the team has been. The best Chelsea-centric analogy I can give you is this: let’s say that the Ricketts are in charge of the club by the end of April, so finances are restored and all the restrictions have been lifted by the end of the season. June comes around and they look at the expiring contracts of Cesar Azpilicueta, Andreas Christensen and Antonio Rudiger and decide they’d rather not put in the effort of negotiating with any of them. Thus, the Ricketts happily send the trio packing. Next season starts, things aren’t going great as the team hits its annual December-January slump. Seeing this downturn in form, on deadline day of the winter transfer window, the Ricketts suddenly sign off on cut-rate deals to sell Kai Havertz, Mason Mount and Reece James with no intention of reinvesting in replacements.

That’s basically what happened to the Cubs last season. A handful of talented veterans on expiring deals were shown ambivalence and three of the most important stars on the team were suddenly jettisoned midseason, something that was as emotionally wrenching for the players themselves as it was for the fans. All in an effort to cut back on spending in a world where spending is the only realistic road to success.

Brutal, stupid and completely unfeasible in football.

All things considered, the Ricketts haven’t done anything with the Cubs to suggest they’ll maintain or improve Chelsea’s current standing as one of the premier clubs in the world. Their reticence to spend consistently, their willingness to engage in tanking as a cheap means of talent acquisition and their apparent lack of concern for fan sentiments regarding roster moves all ring alarm bells. No owner is ever going check every box perfectly (including Roman Abramovich), but the Ricketts family just doesn’t seem to check many at all.

Of course, there’s the extra factor that The Raine Group and Chelsea’s board is looking for in a potential owner: experience in stadium renovations. Stamford Bridge could certainly use a reworking, but the state of Wrigley Field and the surrounding area prior to the 1060 Project was pretty shocking for a place as hallowed as the Cubs’ home ground. The five-year(ish), $575 million(ish) project began in 2014 and revamped almost every aspect of the stadium and the neighborhood surrounding it. On an infrastructural level, the area is better off for it.

Newer construction methods, better facilities and modern technology have provided both a visual facelift and fundamental reconstruction to prepare the franchise’s home for another 100 years of use. But it hasn’t come without its costs.

The main gripe you’ll hear from fans and ticket holders is that many of the new features are plastered with branding and advertisements from tip to tail, which degrades the character and uniqueness of the stadium and surrounding area. We all probably need to grow up a bit when the topic of corporate sponsorship and advertising revenue comes up, but in this particular case, it signals a potential issue for any potential project to upgrade Stamford Bridge. By most accounts, the branding and advertising in and around Wrigley Field is what funded the project in the first place, meaning it wasn’t necessarily a product of any direct investment from the Ricketts.

There’s a chicken and egg question here about what money goes where and who gets paid when, but it seems the Ricketts didn’t really pay for the renovations. This should call into question how they intend to fund renovations at Stamford Bridge, which would be far more expensive and rely on a different set of business regulations. It’s also worth remembering that it took six years to even start the 1060 Project, despite it being one of the things the Ricketts claimed an intention to do when they bought the team. Serious plans for renovating the Bridge have been in place for a long time now, and yet they’re just collecting dust now after seeming to be on the precipice of beginning just a few years ago.

Exorbitant cost notwithstanding, the political knots that need massaging to get a project of this magnitude done in London will take a degree of maneuvering, schmoozing and ingratiating oneself with the powers that be that could set the project back by a decade. That is, if it’s the Ricketts themselves—who don’t seem to have a notable foothold in London—trying to build those relationships. Stamford Bridge needed a renovation 10 years ago, putting it off for another 10 years isn’t acceptable. It’s not just a vanity project, it’s something a club must do to maintain its status at the top of the game. Suffice it to say, the stadium renovation aspect of the Ricketts’ candidacy is suspect at best.

To wrap up what has been a far-too-long diatribe, the Ricketts family just doesn’t have much to offer beyond “they own a sports team.” Almost every aspect of their bid package can presumably be overshadowed by another candidate. The Todd Boehly consortium has many of the same traits as the Ricketts’ bid (baseball, stadium renovation experience, etc.), but includes extra features like connections within London, a standing interest in purchasing Chelsea before the current political upheaval and a track record of investing in women’s sports.

An ideal next step in the process may be the Boehly and Sir Martin Broughton groups one-upping one another with promises and guarantees, with this additional “True Blue” consortium tacking itself on to the preferred bid. Either of these other two finalists pave a more promising path into the future for Chelsea compared to what the Ricketts can realistically offer.

There’s one undeniable positive for the Ricketts, however: they aren’t Woody Johnson.