Longstaff is reportedly growing into a more influential figure in Canada. The report says he captained Montreal in a recent draw with Portland, stepping up when the club’s regular leaders began on the bench.
The midfielder reportedly described the experience as special, while stressing that leadership does not depend solely on wearing the armband. That attitude has helped shape his adaptation to life in North America, where distance from family and a different football culture have accelerated his personal development.
His route has not been straightforward. After emerging at Newcastle, Longstaff spent time on loan with Aberdeen, Mansfield Town and Colchester United before rebuilding his career in Canada following a serious knee injury.
A future clash with Inter Miami would carry a familiar challenge. Longstaff has already faced Messi during his time with Toronto FC, and the possibility of another encounter has clearly caught his imagination.
Before that fixture, however, Montreal’s immediate focus is reportedly the Canadian Championship quarter-final against Vancouver FC, followed by an MLS meeting with Toronto. Those matches will test whether Longstaff’s growing authority can help a team whose campaign has been uneven.
The report says Longstaff’s contract is due to expire at the end of the year, potentially making him a free agent. He is reportedly keeping his options open, including a return to Europe if an attractive opportunity emerges.
At the same time, Longstaff is said to be happy in Montreal and encouraged by the growth of MLS. That leaves him with a genuine choice rather than an obvious exit route.
The next fixtures could influence both sides of the decision. Strong performances against Vancouver, Toronto and eventually Messi’s Inter Miami would strengthen Longstaff’s case-whether he chooses to remain a leader in Montreal or seek his next challenge elsewhere.