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Then captain of the Scotland under-21 team, Caddis joined the Town on a three-year deal in August 2010, after Swindon agreed an initial combined fee of £350,000 for the defender and Simon Ferry with Celtic after an initial offer, was turned down - the deal including clauses that could potentially take the fee up to £600,000. The capture of Caddis ended an eight-month pursuit by manager Danny Wilson, who had attempted to sign him during the previous transfer window in January, and again on loan before the season was out.
After sitting out the first game of the season, Caddis made his Town debut in the Carling Cup against Leyton Orient, before making his league bow in a 2-2 draw at Hartlepool that Saturday, with Swindon coming back from two down to draw 2-2. Battling for the right-back berth with Kevin Amankwaah, Caddis remained in the side until the end of August, when he missed a goalless draw at Carlisle whilst on international duty. When he returned, initially he found himself dropped to the bench, before returning the following weekend for a win at Walsall in a central midfield role. At the beginning of August, Caddis played on the right-side of midfield at Dagenham - before his final under-21 appearance for Scotland again saw him dropped to the bench, though he soon returned. Wilson seemed to prefer Caddis in a midfield position - despite an injury to Amankwaah keeping him out of the side, youngster Nathan Thompson and Scott Cuthbert (usually a centre back) were both played at right-back, with Caddis in midfield or out of the side completely. After spending the whole of November on the bench - a period in which he was called up to the Scotland senior side for the first time - Caddis finally returned to a right-back role at the end of the month for an FA Cup tie at Crawley, and after giving a good performance, he kept this position right through until the end of January, when defeat at fellow relegation candidates Bristol Rovers prompted Wilson to make wholesale changes to his lineup. Two games later, Caddis was recalled - and he netted his first senior goal in a 3-2 defeat at Bournemouth, with a good solo effort.
From that point on, Caddis was ever-present until the end of the season - and despite the Town slumping to the bottom of the table, the Scot was one of the more consistent performers - picking up the Supporters' Club Away Fans Player of the Year award. Over the close-season, new boss Paolo di Canio also hailed his consistency, and naming Caddis as one of his four 'leaders' on the pitch - di Canio also praised Caddis' versatility, hinting that he might utilise him further up the pitch in midfield. This proved not to be the case though - instead, Caddis was almost ever-present in the right back position, and he was joined on the right side by Matt Ritchie, who switched over from the left flank - and the two linked up superbly, the pairing arguably the most feared in League Two. After initially missing out on the captaincy to Oliver Risser, di Canio handed it to Caddis after injury to Risser early in September - when the Namibian returned though, di Canio announced that Caddis would retain the role for the rest of the season.
The Caddis and Ritchie partnership was crucial as Swindon climbed the League Two table after a poor start and also progressed in the Johnstone's Paint Trophy - Caddis himself getting in on the act with a couple of superb goals in December - the first an equaliser at Southend in the JPT which won the 'Ultimate Finish Award' for the best goal of the round, which was followed up the following Saturday with a superb forty yard run and low strike against Bristol Rovers. With the transfer window looming, Ipswich were rumoured to have made a double bid for both Caddis and Ritchie - a suggestion that chairman Jeremy Wray was quick to quash. Caddis netted his third goal in a month at the beginning of January with a curled free-kick against Wimbledon, then in February, Swindon reached the Johnstone's Paint Trophy final - Caddis stating that leading the Town out at Wembley would be one of the highlights of his football career.
Unfortunately, it wasn't to be - after Caddis netted his fourth of the season from the penalty spot at Hereford, and a ten match winning run was brought to an end by local rivals Oxford, Caddis limped out just fifteen minutes into the Town's next match against Dagenham - and though initial scan results on an ankle injury suggested that it wasn't too serious, he suffered a setback after returning to light training. In total, Caddis missed eight games over almost six weeks - and though the Town recorded five victories and six clean sheets without him, his absence was notable, particularly for Matt Ritchie - without the support down the right flank, the Town's attacking play was missing a dimension - and also at Wembley, where the Town were defeated by Chesterfield.
When Caddis did return in mid-April, he came back into a side on the brink of promotion - and a narrow victory over Plymouth in his first game left the Town needing just a point to confirm their ascent to League One. For a moment, it looked like it would be Caddis who sealed it - 1-0 down at Aldershot, the Town skipper netted an equaliser from the penalty spot in front of 1,200 travelling fans - only for the Shots to win the game. Promotion was eventually assured on the following Saturday, despite a 3-1 defeat at Gillingham - Caddis dedicating the promotion to the Town's 'amazing' support. As Swindon went on to seal the championship, Caddis was named in the PFA League Two Team of the Year alongside Matt Ritchie, before agreeing an extension to his contract until the end of the 2013/14 season.
Incredibly though, Caddis had played his last game for Swindon. After featuring throughout the Town’s pre-season campaign, di Canio stripped him of the captaincy the week before the new season started - accusing the Scot of “not being the same player” after becoming a new father over the summer - and then left him out of the squad for the season’s opening games. At the end of August, a deal was agreed to allow him to join Championship side Birmingham on a season long loan, with Adam Rooney moving in the opposite direction - but though Caddis initially impressed at St. Andrews, he was soon sidelined with a shoulder injury. When he returned to action sooner than anticipated, Caddis took a side-swipe at di Canio - stating that maybe it “was not so bad” that he had fallen out with the Italian, as there would have been no chance that he could have got back to fitness so quickly at the County Ground, as the facilities at the Championship side were so much better. Di Canio soon retaliated, saying that he “can’t accept stupid comments from a player who hasn’t proved anything yet in football”, suggesting that Caddis “didn’t even know how to stretch” when he had joined the club - soon after, it was revealed that di Canio had donated his image rights so that the club could benefit from treatment at an Italian rehabilitation center among the best in the world.
By the end of December, it seemed certain that Caddis would join the Blues on a permanent deal - but although a price was agreed, Birmingham pulled out of the deal as it was decided that they couldn’t afford the fee - and a deal was still not in place by the time the defender’s loan deal expired. By this time, a new board was in place at Swindon and di Canio had resigned and was replaced by Kevin MacDonald - the new supremo stating that he expected Caddis back for pre-season, and that he would not be sold on the cheap - Caddis himself seemed bemused at how his situation had worked out, having previously stated that he would “love” to stay at St. Andrews, he admitted that he had expected to have been transferred. Though Caddis started the pre-season campaign - even captaining the side at Forest Green Rovers - he found himself on the sidelines after a Swindon Advertiser interview in which he declared he didn’t know what his future held, or which direction the club was trying to go in - as new bids from Birmingham and Blackpool in the region of £120,000 were rejected. After the season started, Caddis revealed details of a meeting with new Town chairman Jed McCrory in which he was told, as one of the club’s highest earners, his wage would be an issue - going on to accuse the club of not playing him as they wanted him sold. He also stated that both Millwall and Birmingham had agreed to take on his contract on a loan deal - McCrory retorted by saying that he had been disappointed that Caddis had not agreed to return to Swindon to participate in the play-offs the previous season, and that the Scot had told him he wanted to play in the Championship and was looking for a new club. When a bid from Blackpool was eventually accepted, Caddis could not agree personal terms - the contract only marginally better than his Town deal, but dependent on the number of minutes he played. The saga finally came to an end at the beginning of September, when the Town accepted a bid of £150,000 from Birmingham, and Caddis moved to St. Andrews on a three-year deal.
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