BOSTON – It happens each winter.

At some point, writers talk about how tough it is to play in the American League East. We call it the toughest division in baseball, pointing to the post-season success teams in that division have had in the wild card era.

This year, we really mean it.

The AL East has never been deeper. In years past it was a top-heavy division, long dominated by the Red Sox and Yankees.

From 2003-2007, those teams made the playoffs in four out of five seasons.

Indeed, this pair of baseball behemoths went into the season fighting over the division title but still knowing that second-place would bring a postseason berth.

But in 2008, the Rays had joined the party.

This Big Three represented some of the best teams in the game.

Last year the Orioles edged the Rays for the division’s second playoff spot in the newly expanded postseason pool.

The Red Sox and Blue Jays were left on the outside looking in, but they’ve been among the most active teams looking to improve in this offseason.

The Blue Jays improved dramatically by virtue of a 12-team megadeal with the Marlins, while Boston has been called the “winners” of last week’s MLB winter meetings.

In one week, General Manager Ben Cherington added Mike Napoli, Shane Victorino and Koji Uehara to the mix.

It’s not a stretch to think all five teams in the division will enter the season expecting to contend for a playoff spot.

“All five teams, heads up,” said Tampa Bay Manager Joe Maddon last week in Nashville.

“It’s going to be very tight. Respectfully, I think every team is going to have an opportunity to get to the playoffs next year in our division.”

Sox fans aren’t quite ready to pencil their team into a playoff spot just yet.

While the Sox overpaid for Napoli and Victorino (each getting a three-year, $39 million deal), there are still pitching issues to deal with. Uehara is a huge addition to the bullpen, but Boston still needs help in the rotation.

And the cost of decent starting pitching continues to go up.

Kansas City acquired James Shields from the Rays in a deal that involved Wil Myers, one of the top prospects in the game.

While the Sox will be happy not to face “Big Game James” as often next season, they’ll be looking at the long-range forecast of Myers joining Evan Longoria (recently signed to a six-year extension) in the Rays lineup for years to come.

As deep as the AL East might be, there are issues each team will have to deal with.

Are the Rays taking a step back with Shields gone for the prospect of Myers’ future?

Can the Yankees recover from A-Rod’s hip surgery and the turmoil of last October?

Do the Orioles remain a contender now that they are wearing a target on their backs?

Will the Blue Jays jell quickly with all the newcomers?

Meanwhile, the Red Sox have more questions to answer than anyone.

On the plus side, they’ve settled the manager’s situation and have dramatically improved their clubhouse chemistry.

If they can land a starting pitcher — and there are still several quality arms available on the free-agent market — they can rightfully expect to be much better in 2013.

But they’re not alone. They’ll play 76 games against their division rivals next season.

And every one of those games will feature teams that have their sights firmly set on playing in October.

Tom Caron is the studio host for Red Sox broadcasts on the New England Sports Network. His column appears in the Press Herald on Tuesdays