The Blues invested £135million in Moises Caicedo and Robert Sanchez in the recent summer transfer window, with talks over the Ecuadorian midfielder running for several weeks before a surprise swoop from Liverpool was rejected and the two clubs were forced back to the negotiating table.
Marc Cucurella, Billy Gilmour, Levi Colwill and former Chelsea boss Graham Potter have also been traded between the teams in recent years - and few could blame Bloom for being exasparated by the situation.
However, he has admitted that he would have no qualms with doing business with the west Londoners again.
“We take each situation on its own merits and each one is separate,” he told The Athletic.
“When Graham went, that was six of our staff all in one go, but we just look at it all individually and every deal is a separate deal and the fact it happens to be one club is the way it is.
“It’s possible over the next two or three years that we have no dealings with Chelsea. So, for me, it’s not personal at all and each individual deal I’ve got to do what’s best for the football club first and foremost.
“If other clubs are interested in our head coaches, staff, players, I much prefer it that way than no one’s looking at any of our players or staff. So, we’re doing something very right. We do everything we can to keep our best players, but we know in the way of the world that won’t always be the case.”
Brighton striker Evan Ferguson is the latest young star to emerge out of the Seagulls and onto the gossip columns, amid talk of Chelsea being among several clubs interested in a player reportedly valued at £120m.
“I’m extremely excited about Evan Ferguson, as I am by lots of our young players who are also playing phenomenally well,” Bloom said. “But I will let others talk about the potential and what it may be.
“He doesn’t need me to put any more pressure on him. He’s a great young man, he’s got a superb temperament, and I’ll just let him develop and see what happens.”