The departure of both Sir Alex Ferguson and chief executive David Gill at the end of last season was always going to be a difficult double whammy for Manchester United to overcome. Though Ferguson was rightly seen as the biggest loss after 27 years and 13 league titles with the club, Gill's brilliance behind the scenes over the last decade has also been invaluable to their efficiency and consistent success. But now they're both gone, replaced by former Everton manager David Moyes and promoted commercial operations expert Ed Woodward, and the difference between the old regime and new was comically noticeable during the summer transfer window.
Under the cloud of Wayne Rooney demanding a transfer (again) before the end of last season, the club's transfer dealings started innocently enough with the signing of 20-year-old Penarol defender Guillermo Varela for a little over £1 million in early June, a few weeks before Woodward and Moyes officially began in their new roles. But while everyone was busy laughing at Arsenal for their own transfer market failings, Man United were not so quietly going down a similar path that, shockingly, wouldn't end nearly as well as it did for Arsenal.
They launched a very public pursuit of Barcelona's Cesc Fabregas, who eventually said he didn't want to move at all even though Man United wasted their time with multiple bids. They then made a futile attempt at bringing Cristiano Ronaldo back from Real Madrid and angered Moyes' former club with a join bid for Marouane Fellaini and Leighton Baines that was labeled "derisory and insulting."
In the midst of all of this was the ongoing saga of an "angry and confused" Wayne Rooney attempting to passive-aggressively force a move to Chelsea without actually forcing a move to Chelsea. But the new regime won praise for standing up to the wantaway star's games and finally getting him to resign himself to staying (again). Had the transfer window ended right there, it would've been disappointing not to have any big new signings, but not embarrassing. Keeping Rooney was important, after all. Unfortunately for Woodward and Moyes, it didn't end there.
After having a £25 million bid for promising 24-year-old Athletic Bilbao midfielder Ander Herrera rejected, Man United were reportedly willing to trigger his £30 million buyout clause to get a deal done. And that's when things got weird.
Three men who showed up at La Liga headquarters to complete the necessary paperwork late in the day supposedly turned out to be "impostors" doing so without the club's consent. That ended that.
With time running out, there were rumors of a £35 million bid for Real Madrid midfielder Sami Khedira being flatly rejected before Man United finally refocused their efforts back on Fellaini and Baines, while also trying to work out a literally last-minute loan deal for Real Madrid defender Fabio Coentrao.
As the man recently in charge of such things, Moyes knew better than anyone that Fellaini had a £23.5 million buyout clause that expired at the end of July. Yet when he finally got around to completing a deal for the big haired Belgian, the time wasting and derisory bids ran the final price up to £27.5 million. Still, a deal was finally done and help was needed in the midfield. A £15 million bid for Baines didn't work, though.
The Coentrao deal had everyone guessing even after the deadline passed. The result: no go because the paperwork wasn't completed in time. Perhaps they should have called in those go-getting impostors from earlier in the day to help them out.
Of course, change after a freakishly long period of success and stability is never going to be without difficulties and as reigning champions, keeping Wayne Rooney and adding Fellaini might be all that's needed (for now). And finding someone to take Bebe, one of the rare mistakes of the previous bosses, on loan was also a tiny miracle. Still, no new regime wants "humiliation" to be the first word in a major newspapers review of their first attempt at transfer wheeling and dealing at Manchester United.
Meanwhile, the once hilarious transfer stylings of Arsenal totally changed the script and won the hearts and minds of the deadline day audience while further highlighting Man United's goof-ups by pulling off a perfectly executed club record signing of Mesut Ozil. However, they did end up keeping Nicklas Bendtner.
It could've been much, much worse for Woodward and Moyes, though. At least they didn't misplace Patrice Evra's internal organs or sell Old Trafford for magic beans. They could have decapitated the Sir Alex Ferguson statue while looking for more money and given Robin van Persie back to Arsenal just because it was "the right thing to do." They didn't do any of that. A perfect four for four there. So they've got that going for them.