Josh Bailey had his most productive season playing on John Tavares’ wing, and the Toronto Maple Leafs would be a better team if they trade for him

The Maple Leafs have a hole in their top-six forward group. While their first line is one of the best in the league, Tavares and right-wing William Nylander could use a new linemate.

Rookie forward Nicholas Robertson currently occupies the second line left-wing slot beside Tavares. Robertson has two points in 12 career NHL games and another eight points in nine AHL games with the Toronto Marlies. He’s a former second-round pick with tremendous upside.

The Maple Leafs might be skeptical giving Robertson such an important role down the stretch. Toronto is hungry for a Stanley Cup, and they could use some veterans to help them get one.

The Islanders lack youth, speed and skill. Robertson brings all these attributes to the table — though head coach Barry Trotz will have to trust him with elevated minutes and coach him through any mistakes.

Bailey for Robertson could be the start of a deal, but the Leafs have more needs to fill. The team needs right-handed defenders, a position of strength for the Islanders. Scott Mayfield, with his lowly $1.45 million salary cap hit, could be a prime target. He played significant time on the Isles’ top pair with Adam Pelech, proving he can provide reliable defense throughout a team’s lineup. Losing him would be a tough pill to swallow for the Islanders, though.

The Leafs could also use some cheap defensive depth, and 39-year-old Andy Greene is a great option. He could play both the right and left sides and his cap hit for the remainder of this season ($750,000) is extremely low.

In return, the Islanders can acquire Jake Muzzin. The 33-year-old defenseman is currently on long-term injured reserve and is likely out for the season with a concussion. This is an acquisition for next season.

The Islanders are in need of a left-handed defenseman to play with Noah Dobson on the second pair, and Muzzin fits that role perfectly. He’s the ideal combination of shut-down defense and offensive awareness. If he’s healthy, he’s just what the doctor ordered for the Isles. If not, he could stay on LTIR and not count against the team’s salary cap.

The Islanders should also request a draft pick considering the number of assets heading to Toronto. A third round pick next year — with the condition that it becomes a second rounder if the Leafs make the Stanley Cup Finals — sounds fair.

This would not be an easy trade for either team to complete. Robertson is arguably the Leafs’ top prospect, and the Leafs would have to maneuver around the salary cap to fit in Bailey and Mayfield’s long-term contracts. That could mean sending down a forward or the Islanders retaining salary. They will also need to move assets in the offseason to re-sign some RFAs and UFAs as well as account for Morgan Reilly’s contract extension.

The Leafs could make an easier trade for a rental — perhaps the Anaheim Ducks’ Rickard Rakell. But if the Leafs see something in Bailey, the trade could work.

This trade gives the Maple Leafs stability at crucial positions within their lineup. Bailey is a veteran second-liner who’s succeeded in the past with Tavares. They’re also getting two reliable defenders who could play significant minutes with any defense partner.

The Islanders get key future assets. They get a potential first-line winger, a second-pair defenseman and a draft pick. Those are exactly the assets the Islanders need to prioritize in a year their playoff odds have shrunk to 3%. It would be tough saying goodbye to Bailey (and harder seeing him with Tavares again), but it’s a change that must happen at this stage in Islanders’ history.

Ben Baruch

Born and raised on Long Island. Isles fan since 2009. Studying journalism at the University of Maryland, College Park.