This article is part of Football League World’s ‘Terrace Talk’ series, which provides personal opinions from our FLW Fan Pundits regarding the latest breaking news, teams, players, managers, potential signings and more…
FLW's Middlesbrough fan pundit Dana Malt has offered her verdict on the club's worst signings of the last ten years as we approach the January transfer window.
With Premier League campaigns and poor spending in recent years, there has been plenty of good and bad pass through the doors at the Riverside.
The club are seemingly just starting to recover from poor recruitment following their season of high spending under Garry Monk as Michael Carrick looks to piece together a side capable of pushing for promotion.
Whether that's achievable or not this season is another question, but there's certainly enough quality to get them there.
The same can't be said however for these three signings, as Dana has narrowed down a list of Middlesbrough's worst signings ever to three players.
Let's take a look at who she selected..
3) Adlene Guedioura
The Algerian international arrived at the Riverside with a high reputation after helping Watford to promotion.
His ability to excite crowds with his ball-playing ability and habit of scoring from distance won him the hearts of many supporters at his previous clubs with Middlesbrough one of the exceptions.
He signed for Boro in January 2017 on deadline day but made just six appearances on Teeside. He would later sign for Nottingham Forest the following January cementing his place as one of the worst signings in recent history.
2) Dwight Tiendalli
This is very much a blink and you'll miss it transfer as the experienced Dutch full-back arrived on Teeside on loan in 2015.
Aitor Karanka brought him in to assist with Boro's promotion charge but Tiendalli struggled. After signing in March, he made his debut a month later in a 2-0 defeat away at Watford before sitting out the next four games. The club then opted to terminate his loan and he returned to his parent club Swansea City.
Just a few months later, his contract was terminated by the Swans and was out of the game for almost two years before signing for Oxford United in 2017.
1) Rudy Gestede
Similar to Guedioura, Gestede signed in January 2017 in a bid to assist with Boro's battle against a return to the Championship but was unsuccessful.
He joined the club for a fee in the region of £6m and will go down as one of the worst signings signings ever.
The Benin international managed just six goals in 59 games spread across three years and was released by the club after he refused to sign a new deal that would extend his contract to the end of the 19/20 season which was impacted by Covid.
Speaking of that situation, then manager Neil Warnock said: "I had a good chat with Rudy, I asked him to stay but he said he wasn't prepared to do that.
"I said ‘you might as well go home now’. I sent him off on Thursday, there's no point in doing anything else."