The 20-year-old, who made his Hearts debut at the age of just 17, has signed for the part-time Capital club after being released by Inverness Caledonian Thistle.
McDonald has struggled with injury throughout his short career and his most recent spell at Inverness was no different.
But Naysmith, who has monitored the player’s progress from his time as loans manager at Hearts, moved quickly to snap him up after his release.
He is comnvinced the opportunity for McDonald to play regularly at League 2 level will benefit both player and club.
Naysmith explained: “Due to several different reasons, Anthony’s career hasn’t progressed as he would have liked or expected over the last few seasons and from talking to him over the last few days he realises he needs to get his career back on track.
“To do that, he needs to play consistently well, week in, week out and I am delighted that we have agreed a deal to bring him to Edinburgh City to give him the chance to do just that.”
McDonald was signed twice by former Caley manager and Jambo legend John Robertson – first on loan and then again on a free transfer in February 2021.
But just after signing for Inverness last year, following a brief spell at Spanish club Córdoba, McDonald suffered an injury that ruled him out of the rest of the 2020/21 campaign.
He returned to action at the start of this season and played against Hearts in the Premier Sports Group Stage at Tynecastle, making five appearances in all competitions.
McDonald initially joined Hearts at under-14 level from Livingston and made his first team debut, aged 16, in December 2017, playing from the start in a 2-0 win against Dundee and providing the assist for the opening goal.
He was subsequently loaned out to Dunfermline and Inverness, but made 25 first-team appearances for Hearts overall, mainly from the bench.
After being released by Hearts, he signed a two-year deal for Spanish club Córdoba CF in October 2020 before returning to Scotland to re-join Inverness a year ago.
It hasn’t worked out, but Naysmith knows McDonald has the raw attributes required to play at a higher level. The forward just needs a run of games and to stay injury free. If he does so, Naysmith is convinced he will be a big asset for City.
Naysmith added: “Anthony is an attack-minded player with really good ability, quick feet, decent pace and someone who can play in several positions.
“He will give us different options in attack. He is someone who I got to know a little when I was loans manager at Hearts and since then I have continued to watch his career with interest.
“Although only 20, he has played in the Premier League for Hearts and in the Championship for both Inverness and Dunfermline, so hopefully his experience of playing at a higher level will benefit the team.”