St. Patrick's Day Collection | T-Shirts, Hoodies, Crewnecks, Hats, FlagsSHOP NOW

Dan Gilbert, And His Complicated Ownership History, Have Joined A Bid To Buy Chelsea

One of the biggest sports franchises in the world was forced onto the market when the UK government sanctioned Chelsea owner and Russian oligarch Roman Abramovich last month. This brought every billionaire looking for a new toy out of the woodwork as they tried to crew up and purchase the football club that is reportedly worth around $3 Billion.

One of the leaders in the clubhouse is a group led by The Ricketts family, which also owns the Chicago Cubs. That group just got a little bit stronger (and a lot richer) by reportedly adding one of the richest men in America, Cavs owner Dan Gilbert, to the group according to Sky Sports.

Sources said on Saturday evening that Rock Entertainment Group had agreed to invest a significant - though undisclosed - sum in the bid.

The emergence of Dan Gilbert, one of the richest people in America with wealth estimated by Forbes magazine at almost $31bn, as a participant in the auction raises the stakes still further as a quartet of bidders vie to succeed Roman Abramovich as Chelsea's owner.

As well as the Cleveland Cavaliers, REG owns the Cleveland Monsters ice hockey team, and the NBA G-League team Cleveland Charge.

The Ricketts’ bid had been met by protests because of brother Joe Ricketts’ (not involved in the bid to buy the team) leaked email from 2019 where he called Muslim people “my enemy.” Sounds like a swell guy.

The reasoning behind adding Gilbert’s Rock Entertainment Group to the group, aside from his money and experience running a championship level franchise, was the Cavs track record of diversity and inclusion.

A bid insider said the Cleveland Cavaliers' focus on diversity, equity and inclusion programs could help to allay any lingering concerns among Chelsea's fan-base about the consortium's suitability as owners of Chelsea.

They also pointed to the philanthropic endeavours of Mr Gilbert and his wife Jennifer, who have pledged $500m towards community revitalisation projects in Detroit.

A person close to them said they had also signed The Giving Pledge in 2012, promising that at least half of their combined wealth would be donated to philanthropic causes at the end of their lives.

The Cavs are a model franchise when it comes to hiring and promoting women and minority candidates. Lindsay Gottlieb was an assistant coach for the team before she left to take the head coaching job at USC and the Cavs currently have a black coach in JB Bickerstaff. Numerous front office positions are held by black and female employees. Koby Altman, Stefanie Meade, and Tracy Marek are just a few of the many names you can point to illuminating the team’s commitment to creating a diverse work environment.

There are certainly debates to be had about Gilbert’s business dealings outside of the Cavs, which include his own private police force in Detroit and a $32.5 Million settlement with the Justice Dept. for predatory lending accusations, but you cannot deny the man is one of the most successful businessmen in recent memory.

For now though I just want to focus on Dan as a sports owner.

His tenure as Cavs owner has been a rollercoaster to say the least. And not the fun new ones that turn and flip smoothly. I’m talking an old wooden dangerous son-of-a-bitch where you take your life in your own hands every time you step in line.

The franchise failed to win a championship in LeBron’s first stint, which then ended with the infamous letter Dan Gilbert fired off in comic sans claiming the team would win a title before LBJ. They didn’t. But they did lure LeBron back for a second stint and captured that elusive title giving the city their first one in over 50 years. “Cleveland, this is for you!!!” (but probably not nearly as much for Dan knowing LeBron’s feelings about the team’s owner).

Until this season, however, the Cavs had been one of the worst franchises in professional sports without LeBron on the floor and owned the longest losing streak in all of the four major sports at 26 straight (it has since been broken by Philly with 28 losses). And to many around the team, the rise of this competitive version of the Cavs coinciding with Gilbert’s absence from every day basketball operations is no coincidence.

Gilbert was the hand that led the sometimes curious, but always knee-jerk reactions from the Cavs front office. There are plenty of stories about unhinged late night texts from Dan to beat reporters berating them for critical articles they had written. Not to mention he has been notoriously cheap when it comes to paying his general managers. The most famous instance was him refusing to pay David Griffin which reportedly all but torpedoed a Kyrie Irving for Paul George trade and paved the way for LeBron to leave a second time.

Instead Dan steered the team towards trading Kyrie Irving for Isaiah Thomas and a trash heap, which led to this infamous LeBron IG post.


This sparked a tidal wave of Arthur memes, which is a period of meme history I think we would all like to forget.

Despite all that, the Cavs are at the forefront of pop culture and marketing with creative director Daniel Arsham and a highly regarded team of marketers behind him. Gibert does have a championship under his belt and has led efforts to revitalize two midwestern cities many thought were dead and gone. He helped get gambling approved in Ohio, and despite never delivering on his promise to build a new casino on the river in downtown Cleveland, there is gaming readily available next to the arena in which his basketball teams plays.

If you asked 20 different people what they think of Gilbert you will likely get 20 different answers depending on where they are from and what their interactions were with him. The one thing that every one of them would say, however, is that he is passionate about his sports teams winning and will spend whatever it takes to make that happen. So if that’s what Chelsea fans are looking for then they found the right guy. Everything else is up to personal interpretation.




Now enjoy the last 3:39 of Game 7 where the Cavs completed their 3-1 comeback over the Warriors and captured their first NBA title. I’ll be over here crying tears of joy if you need me.