Gregorio started his career in A.C. Cesena. He was the member of the youth reserve B squad in the 2007–08 season for Berretti reserve league.[2] Reserve A and B merged in 2008–09 season, as the Cesena first team was relegated at the end of 2007–08 Serie B, thus the reserve A was no longer eligible for the Campionato Nazionale Primavera (the youth national "spring" league). Gregorio remained in the reserve for 2008–09 season.[3] He followed the under-20 reserve returned to the spring league in 2009–10 season, but only played 13 times.[4]
On 29 June 2011, one day before the closure of 2010–11 financial year, Cesena formed two swap deals with Bologna F.C. 1909, which Gregorio was transferred to the capital of Emilia along with Kadir Caidi in co-ownership deal for €1 million and €750,000 respectively.[5][6] At the same time, Giacomo Bassoli and Jacopo Luppi moved to Romagna in the same formula.[5][6] The deal made the clubs had a financial boost instead of immediate impact on the squad.[nb 1]La Repubblica had criticized Bologna's swap deal with Livorno and Chievo in the same month were exploit to the transfer market to fix the balance sheet.[7]
Lega Pro loans
Gregorio left for Italian fourth division newcomer Santarcangelo in July 2011, along with K.Caidi[8] (both from Bologna/Cesena), G.Bassoli (from Cesena/Bologna), Rivolino Gavoci, Nicola Del Pivo and Daniele Ferri (Cesena only). The club also renewed the loan of former Cesena teammate Simone Tonelli, however now co-owned between Vicenza and Cesena. In June 2012 the ownerships were renewed. Gregorio left for Pontedera in 2012–13 Lega Pro Seconda Divisione.[9] In June 2013 both clubs gave up the remain 50% registration rights on their youth products. On 18 July 2013 he was signed by Teramo.[10]
Footnotes
^The all four players signed a 3-year contract, which both K.Caidi and Gregorio had an annual wage of €28,757 each.[5][6] Among the four players, only K.Caidi had a brief professional experience in 2010–11 Lega Pro Seconda Divisione. However the aggressive price tag made Cesena had a profit of €2M (Gregorio) and €1.5M (K.Caidi) respectively,[6] while Bologna had a profit of €2M and €1.5M for G.Bassoli and J.Luppi,[5] as youth product previously did not have a value as an intangible asset. As it was a pure swap deal, the increase in asset only in form of increase in intangible asset instead of cash (Bologna: Gregorio & K.Caidi; Cesena: G.Bassoli & J.Luppi). In June 2011 both clubs also made swap deal with other clubs, which both clubs eventually had a positive net equity (net asset) in order to register in 2011–12 Serie A without re-capitalization. On 30 June 2011, Cesena had a positive net equity of €502,106,[6] but boosted by new signing of G.Bassoli (€2M), Palumbo (€2M), J.Luppi (€1.5M) and Bonicelli (€1.2M). While Bologna, had a positive net equity of €18,990,427 on 30 June 2011,[5] which the club already received an equity contribution of €21,049,381[5] but the net equity was also boosted by new signing Pasi (€3.2M), Rickler (€3M), Gregorio (€2M) and K.Caidi (€1.5M). Moreover, half of the transfer fee of Nico Pulzetti (half of €3.3 million) was paid by Riccardo Regno (€1.65M tag).[5]
Moreover, as company had to "weather" its intangible asset by amortization, Gregorio and K.Caidi would have made Bologna have an amortization cost of €1,166,666 each seasons from 2011 to 2014 if both players eventually worth nothing. Moreover, both clubs had to pay VAT.