Antonio Conte missed out on two of his top transfer targets, saw a key player sold against his wishes, and feels the current Chelsea squad is ill-equipped to handle the addition of the Champions League to its schedule.
No wonder the Italian coach cuts a frustrated figure heading into the start of Chelsea's Premier League title defense.
Going into Saturday's home match against Burnley, it could even be argued that Chelsea is beginning the season in a weaker position despite a summer outlay of around 140 million pounds ($180 million).
So much for building from a position of strength.
Will new striker Alvaro Morata be as effective up front as Diego Costa, who has been told by Conte via text message that he isn't part of his plans? Is new midfielder Tiemoue Bakayoko a significant upgrade on Nemanja Matic, who was sold to rival Manchester United in one of the most head-scratching moves of the summer window?
Chelsea was beaten to the signature of striker Romelu Lukaku by United, while Conte has also acknowledged that he tried to sign right back Kyle Walker, who ended up leaving Tottenham to join Manchester City.
It leaves Chelsea needing a new midfielder as well as reinforcements at wing back in the final days of the transfer window. Conte clearly wanted his squad in better shape at this stage, especially considering City and United — potentially Chelsea's biggest challengers this season — have been more decisive in the transfer market.
"It's very important to try to find the right solution, to try to improve the squad," Conte said this week at the Premier League launch.
Conte referenced the last time Chelsea defended the league title. It was the 2015-16 season and the team finished embarrassingly in 10th place, with coach Jose Mourinho fired before Christmas.
"For sure we want to avoid the Mourinho season," said Conte, although that really would be the worst-case scenario.
Things are more comfortable on the personal front for Conte, who recently signed a new, improved contract and will have his family — wife Elisabetta and daughter Vittoria — living with him in London this season. He has a year's experience of the Premier League and of English culture behind him, too.
This season will undoubtedly be tougher, though.
The last team to retain the Premier League was United in 2009 and Chelsea, which wasn't in European competition last season, now has the Champions League clogging up the schedule. United and City will be a tougher prospect now Mourinho and Pep Guardiola have something close to their ideal squads.
In the short term, Chelsea starts the season with Eden Hazard and Bakayoko out injured, while Morata is still getting used to his new teammates and may take the time to settle. The Spain striker is even likely to start on the bench against Burnley, with Michy Batshuayi starting.
Here are other things to look out for in the opening round of the season:
The season starts with uncertainty surrounding the future of a number of high-profile players.
Leicester winger Riyad Mahrez and Southampton defender Virgil van Dijk have both handed in transfer requests this offseason but have yet to seal a move. Mahrez could feature against Arsenal on Friday, but Van Dijk is currently training away from the Southampton squad and won't play against Swansea on Saturday.
Swansea coach Paul Clement said Thursday that Gylfi Sigurdsson will not be part of the squad for the match at St. Mary's Stadium, amid interest in the midfielder from Everton.
Meanwhile, Liverpool playmaker Philippe Coutinho and Arsenal forward Alexis Sanchez are the subject of interest from Barcelona and Paris Saint-Germain, respectively, but their clubs say they will not be sold. Sanchez is currently out with an abdominal injury, according to Arsenal manager Arsene Wenger, while Coutinho has missed training sessions this week with a reported back injury and could be unavailable against Watford on Saturday.
Wayne Rooney will make his first league start for Everton since returning to Goodison Park from Manchester United, but it will be his third competitive appearance in his second spell with his boyhood club.
Rooney also played in both legs of the Europa League third qualifying round against Slovakian side MFK Ruzomberok. Playing as a striker, he didn't score in either match.
Everton opens its Premier League campaign at home to Stoke.
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