Richard Arnold and Ed Woodward are friends, the pair both graduated from Bristol University and they share the same background in finance. They are Glazer acolytes.
Neither man should have found themselves with such power at Manchester United but a new era is now on the horizon.
Arnold replaced Woodward as the club's kingmaker in February 2022 when he was appointed as CEO, but he's spent just 21 months in that role and his expected departure was confirmed on Wednesday morning.
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The 52-year-old is the first victim of the change of regime as Sir Jim Ratcliffe's deal for a minority stake is set to be ratified. He won't be the last and his exit was expected along with the arrival of Ratcliffe's investment.
Arnold has been at United since 2007. He acted as the club's managing director from 2013, overseeing huge commercial growth, until replacing Woodward and he sought to distance himself from his predecessor.
That re-brand always seemed like an impossible task given their links and Arnold was ultimately another symbol of the Glazers' shackling ownership, which is why his departure will be celebrated.
Just a few months into his reign as CEO, supporters organised a protest outside of his home and the plan was foiled by Arnold himself, which led to a sit-down conversation in a pub which was covertly recorded and widely shared on social media.
Arnold discussed the Glazers' ownership, protests, commercial business, transfer policy and more. The reaction to the conversation was mixed, but most respected him for having the gumption to meet supporters.
"What’s happened is we have f***ing burned through cash," was the most memorable soundbite and Arnold insisted he wasn't there to defend the Glazers but working under the Americans spoke for itself.
Woodward was grossly unqualified to be hands-on in the running of the football side of the club and Arnold delegated responsibility when he became CEO, notably empowering football director John Murtough.
Arnold and Murtough were responsible for the appointment of Erik ten Hag from Ajax and they were convinced the Dutchman was the right person to take the club forward after impressing in interviews.
The leadership team was restructured with Arnold in charge and there were different voices present on investor calls, instead of Woodward single-handedly steering the ship.
Murtough was appointed as the club's inaugural director of football a year before Arnold was named CEO and he was keen to reiterate the chain of command had changed in the now-famous pub conversation with fans.
"Here's the money, John you are the f***ing director of football, Erik you are the manager, who do you want?" Arnold said and he was later pictured in Barcelona with Murtough that summer for talks to sign Frenkie de Jong.
Arnold stepped away from footballing matters and focussed on what he had expertise in, which was the business side of the club, and he recently oversaw the completion of sponsorship agreements with Adidas and Qualcomm.
Qualcomm will have their brand Snapdragon on the front of United shirts from next season and the company's deal is said to be worth just over £60m, which is a significant increase on the TeamViewer package.
Manchester City have the most lucrative shirt deal in the Premier League. Their scrutinised package with Etihad Airways is worth £67.5million each season and United now have the second most valuable in the division.
Arsenal and Liverpool, who have long-standing contracts with Emirates and Standard Chartered Bank respectively, are both believed to have deals valued at around £50m for shirt sponsorship.
There have been some positives from Arnold's time as CEO, but many felt his position was untenable due to the Mason Greenwood situation, which became a public disaster for the club in August.
Arnold had planned to confirm Greenwood's return to staff but news of his potential return leaked and there was backlash from supporters, with some threatening to walk away if he represented the club again.
The reaction from fans prompted United to reassess their intention to restore Greenwood to the first-team and a U-turn was eventually made. The right decision had been made but in the wrong way.
The Glazers delegated the Greenwood decision to Arnold and there were questions for him to answer. Why wasn't a decision reached sooner? Why was a return for the player initially planned? Why weren't the views of fans considered?
The U-turn, although around a far more serious and sensitive subject, had parallels with the European Super League debacle, where the club reached a decision before quickly reversing it following intense backlash.
Woodward left the club after the breakaway league collapsed and it was promised that lessons were learned, but Arnold was left with the same accusations as his predecessor and supporters wanted him to be sacked.
Arnold was always expected to leave once Ratcliffe's minority stake was ratified and news of his exit has not been a surprise.
The era of 'Bristol University bankers' running the club is finally coming to an end.
