Paolo Maldini and Ricky Massara’s very quiet January market and 1-0 loss in the derby with Inter left Milan supporters disappointed, and with more questions than answers on the true intentions of RedBird, writes Matt Santangelo.

Gone as quickly as it came, the January transfer window closed for business last week, with Premier League giants Chelsea asserting their dominance on the market with a historically high spending month.

Todd Boehly emphatically put a stamp on the market with a slew of new players, chief among them the late €120m acquisition of Milan summer target Enzo Fernandez from Benfica.

Meanwhile, in what was deemed a crucial month to help aid Stefano Pioli’s s second half and spiralling out-of-control campaign, the Rossoneri’s lack of resources for directors Paolo Maldini and Frederic Massara left a poor taste in the mouths of supporters.

You cannot point to a single successful summer signing Maldini and Massara made, but the frugal investment strategy on behalf of Gerry Cardinale and RedBird off the back of a league title could not be more disappointing if you are a fan.

Amidst a horrific skid to start the new year, the winter market presented a real opportunity for RedBird to flex a bit of financial muscle and help strengthen a squad that is genuinely lacking in multiple phases.

The recent goalkeeping displays of Ciprian Tatarusanu meant a steady backup for top-choice option Mike Maignan was considered the bare minimum, followed by a winger and a central midfielder. As we saw, management did virtually nothing to bolster the roster.

Devis Vázquez, a 24-year-old keeper from Colombia, was the lone player to walk through the doors of Milanello this past month; a highly underwhelming purchase if you consider the numerous talks held for Atalanta’s Marco Sportiello who would have been an ideal candidate for the job.

While it is hard to project what he can be, in this present moment, Vasquez is not the answer to ease some tension that is boiling over between the sticks.

Then, there was the failed courtship of angsty Roma winger Nicolò Zaniolo whose intentions were clear: he wanted Milan and only Milan.

Though the Italian attacker comes with some baggage due to his wildly inconsistent play and injury sheet, he would be an immediate upgrade over what Pioli currently has and a name capable of the singular moments to drum up chances throughout a match. But the right formula could not be found to strike a deal with the Capital club, ultimately forcing Zaniolo to join Galatasaray in February.

Desperation settled in when Milan worked to strike a deal for Club Universidad de Chile winger Dario Osorio in the closing stages of the market, only to once again show real reluctance to commit any money towards areas of need.

It would be in Maldini and Massara’s best interest to spend in ways that elevate the sporting project, and there is no reason to believe those aren’t the intentions of the Italian directors. However, when RedBird are sanctioning such a restricted budget of €50m over multiple windows to improve an unfinished squad in a constantly ballooning market, one must question the legitimacy of the new owners.

Balancing the wage bill, refusing to extend key players who demanded significant wages above club valuations and cutting cost-effective loan deals favourable to stay the course: that has been done. With two consecutive years of UEFA Champions League football and a league title, there should be a bit more urgency to drive this project forward.

While the sustainability model of running a club like Milan is not lost on supporters and the reality of the Italian football landscape is understood, it is extremely hard to take RedBird’s complacency on the chin knowing how long it is taken the club to climb back to relevance.

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